Talk:Aspirin/Archive 1

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Archive 1 Archive 2

Initial comments

The systematic name for this is listed as 2-acetyloxybenzoic acid. Shouldn't that be 2-ethanoyloxybenzenecarboxylic acid? (Sorry if that sounds pedantic.)

I thought so as well, but PubChem and the CAS registry both say 2-acetyloxybenzoic acid. Bfesser 22:27, 17 February 2007 (UTC)


Small typographical correction: in the synthesis section, I changed 'acylated' to 'acetylated'. -- Kurtis (not registered)


COX is short for cycloxygenase enzyme which catalyses the production of prostaglandins, prostacyclines and thromboxanes from arachidonic acid. Aspirin inhibits this enzyme---bon


Could someone please check the pharmacology of aspirin described here... I thought COX was a type of prostaglandin... --Dweir


Nope, platelet cyclooxygenase is an enzyme that mediates the synthesis of prostaglandins (among other things) - I think there is a mistake though, in the platelet aggregation bit, in that it is thromboxane A2 (TXA2), also produced via a COX-mediated pathway, which is not a prostaglandin as stated, that increases platelet aggregation. Will do a bit more research and maybe edit the article re: effects on MI -- Alex.


I think they bought the Aspirin trademark back together with the American company named Bayer in 1994? The article sounds as if they currently don't have the trademark in the U.S..

They don't--no one does...it was declared generic in a 1921 federal court case, so there's nothing to buy--the mark has no commercial value in the US. Contrary to many stories adrift on the internet, this had nothing to do with the stripping of Bayer's assets during WWI, because the trademark was simply resold along with the rest, and then ruled generic a few years later because of public usage as a generic term.--postdlf

In Europe at least, the patent on the principle should have been expired; effectively other firms than bayer are already producing it. Does someone have better informations on the point?

I can't speak for other countries, but the patent in the US expired in 1917. However, "Aspirin" could have still been a viable trademark even with the patent in the public domain, if Bayer (and Sterling, the subsequent owner of the "Aspirin" mark) had better protected the brand name against use by competitors.--postdlf

128.193.88.189 - Please justify putting disclaimers on articles. It is a slippery slope. --snoyes 18:44 Feb 20, 2003 (UTC)

OK, I found a standard disclaimer on Wikipedia:Wikipedia medicine standards - please use this in stead of any other text. --

snoyes 18:55 Feb 20, 2003 (UTC)


I prefer an article about acetylsalicylic acid and a redirection from aspirin, because acetylsalicylic acid is the active agent and aspirin is only a commercial name ( imagine, what would happen if we include all the commercial names of acetylsalicylic acid ). Applying the generalization principle I suggest include the information in the acetylsalicylic acid article with a reference to aspirin like the first acetylsalicylic acid product.

I agree, aspirin is a common term for it, but it should be under acetysalicylic acid.70.49.36.110 23:30, 20 Apr 2005 (UTC)

I really don't think the last paragraph should be there. It's not well written, and seems to be totally separate from the general feel of the page. It really doesn't give any critical information and mentions several topics that are not explained. Use of acronyms for items not previously discussed and mentioning things still in the research phase are bad ideas for an encyclopedia also.

Aspirin is a BRAND. It has copyright.

It's a BAYER brand for acetylsalicylic acid.

It would be better to redirect aspirin to acetylsalicylic acid

--217.217.9.97 20:43, 31 Oct 2004 (UTC)

Brands are protected by trademarks, not copyright. Aspirin, furthermore, is a generic term in many countries, including the U.S., which means it does not function as a brand. The article explains this. Postdlf 01:18, 1 Nov 2004 (UTC)

Well, though Americans do not care much about other's properties, such as registered trademarks, this is an international encyclopedia and therefore to avoid complications the name of the drug should be used rather than the legally protected name. So main article to ASA and redirect there from Aspirin 84.129.215.116 18:20, 24 July 2006 (UTC)

As far as I can tell, looking at my British National Formulary, Aspirin is the International Nonproprietary Name (INN) and as per Wikipedia:WikiProject Drugs/General/Naming of drug pages, is the name that should be used. David Ruben Talk 01:23, 25 July 2006 (UTC)
That seems pretty clear, and I agree, most people would be looking it up under Aspirin rather than 'acetylsalicylic acid'. An encyclopaedia such as Wikipedia is meant to explain the chemical background to readers who don't know much about it, they are not meant to arm themselves with prior foreknowledge before they come to Wikipedia. If I had never heard of ASA why would I want to rely on a Redirect from "Aspirin" and be confronted by a name which I would only undertand after reading the whole article. I am speaking as Wikipedian. Dieter Simon 21:28, 25 July 2006 (UTC)
Still, it is a registered trademark and a proprietary name to the Bayer AG and therefore has to carry a ® when used in common terms. Using the non-proprietary name acetylsalicylic acid is better, though, because this article should not only be about the original stuff from Bayer but about the drug which is also used in generics. 80.136.198.208 22:11, 20 February 2007 (UTC)
As noted above, the name was genericized in the 20s. Even if Wikipedia's manual of style (see WP:MOSTM) specified the use of ® and ™ on trademarks (it doesn't), the name is no longer a trademark anyway. Zetawoof(ζ) 22:41, 20 February 2007 (UTC)
Even though the name has been STOLEN in some countries, it makes no differences to the fact that it is a proprietary name owned by the Bayer company. The fact that in some countries people don't care about the rights of others shouldn't become the common way. Otherwise you could use chinese counterfeits to describe brand products. Even though the name is illegally used by many U.S. companies, it is still stolen. Wikipedia shouldn't contribute to that. Otherwise, what would you say when I started my own fast food restaurant calling it Burger King? 80.136.198.208 23:47, 20 February 2007 (UTC)
Bayer still maintains the trademark Aspirin here in Canada, and so I was a little surprised to find ASA (by which generics are known here) redirected to aspirin, when products still maintaining trademark already forward to their generic names (as Lipitor does). I went to see if I could find aspirin / ASA in the INN lists, I found these here but didn't see aspirin OR acetylsalicylic acid. Could some one provide reference to the actual recommended (not proposed?) INN entry for ASA to clear this up? From what I read in one of the INN documents, the purpose of the INN is so that NO party could claim ownership over the term... so wouldn't chosing a brand name still held in Canada defeat the purpose of HAVING an INN? I acknowledge an above user had the British formulary in hand, and that I was rather tired when scanning those lists (gah! scans!) but a direct link to the document would be perfect! - BalthCat 07:54, 18 June 2007 (UTC)
The word "aspirin" is recognized as a Bayer trademark by Germany and numerous other countries, but it treated as a generic drug description in the United States, the United Kingdom and France. Trademark rights were seized as an economic reparation under the treaty of Versailles, Article 297, Annex section 5. Use of the "aspirin" trademark in the United States was reportedly sold to Sterling Products by the Alien Property Commission in 1919 (see "Drug, Disincorporated," Time, July 10, 1933). Prior to that, however, Bayer had challenged United Drug of Massachusetts in a United States trademark infringement lawsuit, Bayer Co. v. United Drug Co., 272 F. 505, decided in 1921, mainly in favor of United Drug. Curiously, Bayer's standing to sue was not questioned by the district court decision for that case, but perhaps that reflects failure by the U.S. Congress ever to ratify the Treaty of Versailles. In any event, as of January, 2007, the Wikipedia article's discussion of "aspirin" as a trademark needs review. It claims that "[t]he right to use the aspirin trademark in the United States (along with all other Bayer trademarks) was purchased from the U.S. government by Sterling Drug in 1918." Not according to Time and not likely, since the Treaty of Versailles was not signed until 1919, and possibly not relevant, since the United States never ratified the Treaty. The decision in Bayer v. United Drug recognizes a right of United Drug to distribute bottles for retail sale containing up to 50 tablets labelled with "aspirin" as a generic word, but not to so label larger containers or to engage in wholesale trade using "aspirin" as a generic word. Nevertheless, forty years later containers of at least 1,000 tablets were being sold in the United States by Lit of New Jersey and by perhaps other manufacturers labeled with "aspirin" as a generic word. However, Bayer has not entirely given up in the U.S. It appealed a rejection of an attempt to trademark "aspirina" (meaning "aspirin" in Spanish), but it lost in the Court of Appeals, In Re Bayer Aktiengesellschaft, Ser. 78/212,751, May 24, 2007.

____________________

Made a few changes - removed "including US" for NPOV reasons, aspirin is still used to treat flu (just not in children) and removed the statement that "his reasoning was very much in error", as his reasoning is not actually stated! Dan100 23:29, Dec 17, 2004 (UTC)

But, but, but . . . I thought dextro-glucyloctose was an acetylmorphinol!! lol!

List of countries that have rejected Aspirin as a registered trademark

USA, Sudan, Australia, China, South Africa, Mongolia, New Zealand, Argentina, Indonesia, Angola, France, United Kingdom, Morocco, Mozambique, Cote d'Ivoireand Uganda.

It should also be noted in India and half of African countries, Bayer never registered the trademark. All the countries listed above are countries where Bayer initially owned the trade mark.

Added an image

I added a picture of pure crystals of acetylsalicylic acid under the 'history of discovery' section. I had extracted some from aspirin pills today (using acetone), with plans to hydrolyse it and then make oil of wintergreen with the resulting salicylic acid. I figured I'd take a picture of this first and add it to the Aspirin article.

Methylsalicylic acid

Can someone pharmaceutically qualified check the formula details in the box, such as those altered to "methylsalicylic acid", etc.? I wish people put a sign-on name to an edit. Dieter Simon 00:30, 16 October 2005 (UTC)

Action of salicylic acid?

There's something about the logic of the article that's a little hard to follow. The early sections imply that aspirin was originally discovered as a derivative of salicylic acid, which had somewhat the same pharmacological uses. Later on, though, it claims that aspirin works by acetylating COX:

This happens because cyclooxygenase, an enzyme which participates in the production of prostaglandins and thromboxanes, is irreversibly inhibited when aspirin acetylates it.

Now, obviously salicylic acid doesn't acetylate anything; it has no acetyl group. So why would salicylic acid have the same effects? Please explain. --Trovatore 19:30, 30 November 2005 (UTC)

Answer better late than never: This is an example of scientific ideas changing with time. When aspirin was first commercialized by Bayer in 1899, nothing was known about the mechanism of any drug. Aspirin was considered just a less acidic form of salicylic acid, and assumed (then) to work by being hydrolyzed in vivo to salicylic acid which was supposed to be the real analgesic. The acetyl group was (then) considered just a blocking group to reduce the acidity in the stomach.

However the work of Vane in 1971 disproved this idea and showed that the essential action of aspirin is the acetylation of COX. This acetylation does of course produce salicylic acid as a secondary product, but its biological effect is minor compared to the inhibition of COX.

As for similar pharmacological uses, it is just a coincidence that both inhibition of COX and salicylic acid produce analgesic effects. And the inhibition of COX leads to other effects which salicylic acid does not, for example the anticoagulation effect which is helpful in preventing strokes. Dirac66 23:43, 20 September 2007 (UTC)

Boiling point/decomposition

To answer the question posed in an edit summary, a number of sources specify decomposition upon heating. Here's an example of an MSDS : [1] Edgar181 01:07, 21 January 2006 (UTC)


Test for ASA

There was a standing request in the natural sciences portion of Wikipedia:Requested_articles/Natural_Sciences#Chemical_compounds. I dont know if this request was for analytical or in vitro testing, and I didnt think that it would be appropriate to add a new article on the subject. The request has been present for over a month,so I thought I try to fulfill it here. If you have suggestions on how to better handle this request, let me know. rmosler 10:08, 27 March 2006 (UTC)

Looking at all the information, I think I will reconsider combining the articles and just have a stand alone article on salicylate testing rmosler 10:46, 27 March 2006 (UTC)

SMILES

The current SMILES string used in this artice is CC(=O)OC1=CC=CC=C1C(=O)O. However, the article about this molucale representations says aromatic rings should be in lower case. Furthermore, I'm not really an expert, but I'd say renthesis ahould be used either in the label, the second 1, or in the acidic radical. That said, perhaps CC(=O)c1ccccc1(C(=O)O) is a better representation. jοτομικρόν (talk, email) 20:08, 25 April 2006 (UTC)

I updated the SMILES string to include information on aromaticity. It wasn't really wrong originally, but this way is a bit more precise. --Ed (Edgar181) 20:24, 25 April 2006 (UTC)

The name

"Aspirin" is not an official name of the molecule, it's just one of the drugs that contain acetylsalicylic acid. It's a serious abuse to use name of a product that contains a molecule as a name for the molecute, trademarks or not. Taw 16:40, 9 May 2006 (UTC)

Wrong. Aspirin = Acetyl salicylate. Paracetamol does not redirect to acetaminophen. Paul C 17:59, 9 May 2006 (UTC)
Do you know about at least one scientific source that call the molecule aspirin ? Taw 20:37, 30 May 2006 (UTC)
Goodman & Gilman's Pharmacological Basis of Therapeutics? Paul C 23:08, 30 May 2006 (UTC)
Oh well, I don't like having article about acetylsalicylic acid under aspirin, but if even medical sources abuse it this way, there may be little choice ;-) Taw 15:27, 1 June 2006 (UTC)
Calling the acetylsalicylic acid molecule aspirin is not abuse! You're just being pedantic. It is commonplace in organic chemistry to refer to a molecule by a trivial name such as aspirin. See for example ibuprofen, oseltamivir, cocaine etc.
Ben 16:45, 1 June 2006 (UTC).
I have never seen a box of anything saying it contained acetylsalicylic acid, they all say aspirin202.161.5.252 09:26, 22 May 2007 (UTC)
Come to Canada and buy some ASA! - BalthCat 07:58, 18 June 2007 (UTC)
The Merck Index lists it as aspirin. --Itub 08:03, 26 September 2007 (UTC)

Section called "Aspirin"

Is there any way to make sense of the section under the header "Aspirin"? From the text of the article one can't tell who or where "Sterling" came from. Also, shouldn't that portion of history under the header "Aspirin" be combined with the section entitled "Discovery". The two sections tend to overlap. 24.186.214.2 20:22, 7 June 2006 (UTC)

I might try a better introduction of Sterling Co. Someone took a senence from somewhere and didn't introduce the Sterling company properly.Gaviidae 11:15, 6 July 2006 (UTC)
update: I made a Sterling page but it sucks and needs work. Help. Gaviidae 17:56, 9 July 2006 (UTC)

Aspirin and Cancer

Someone had a citation-less sentence about some recent article proclaiming aspirin's anti-colorectal cancer properties-- as I went to get the actual article, I found so much about aspirin and cancer out there that I made a whole new section, because it didn't seem to belong in the How It Works section anymore. I've sort-of listed the articles in chronological order. If anyone has other significant studies (ie, other parts of the body), please add them. I tried to find the actual studies rather than 3rd-party CNN/BCC-style accounts, so that readers can see the actual papers if they wanted more info. This seem a good idea or is there some Wiki-cancer-aspirin page out there that this should go into??Gaviidae 11:15, 6 July 2006 (UTC)

Thanks for information - the risks of NSAIDs (GI bleeds and incr heart disease) probably outweigh most of the benefits seen - particularly considering the high dosages looked at in some of these studies. Indeed I believe it was studies of COX-II use at preventing Colon cancer which highlighted the recent much reported risks of COX-II as causing heart disease & deaths. With attention now turned to the more conventional NDAIDs (Ibuprofen & Diclofenac), these too seem to have a previously underappreciated coronary risk in long-term usage. So even hinting at use of aspirin for cancer prevention in an "open" source such as wikipedia carries risks (I've admitted several patients in the past with acute gastric ulcer bleeds due entirely to self-medicated aspirin use for "heart protection" when there was no clinical need for them to have done so, fortunately none died). The effects and studies on aspirin on rates of cancer is fascinating though (both on what it reveals about the pathophysiology of cancers and approaches that might be taken to help prevent) - but for now this is purely research, speculation (of what the overall cost-benefit outcome might be), and not part of established medical advice/practice.
  • I've moved it down to the end of the general discussion on (established) use.
  • I don't think wikipedia is the place to discuss at length each single study (vs citing perhaps an official guideline that considers cost-benefits and cites its sources). I grant your prose is well written, but I would prefer in wikipedia to see a more succinct style that does not include in the main text the details of which journal and which team undertook a particular study - my personal feeling is that such information is best included by modifying in-line links to full footnote citations.
I wont for now have a go at compacting down the information you clearly so carefully sourced, as I think it would be useful to first see if other editors agree with your thought that such info might best be served in its own article to which 'Aspirin' then points. Rather than Aspirin effect on cancer, might not the more general NSAID effect on cancer be helpful, given that there has been well reported studies looking at COX-II use for colon cancer that created so much controversy ? David Ruben Talk 13:22, 6 July 2006 (UTC)
Thanks for the comments. I'm not sure how to provide citations to the ideas without citing the actual papers-- and I also mentioned the sizes of the populations (important because smaller study sizes don't weigh as much in my and many others' minds) and who was involved (women in these studies, mostly), and how they did them (for instance, some of these are simply asking people how much aspirin they take, and people are notoriously vague when asked about their habits-- thus I mentioned whether particular studies were questionaire-style or empirical (the actual studies say how correct they think the participants' answers were)). I also mentioned some of the researchers' reservations at the high doses used by some participants (2 aspirin a day, wow). As much as I wanted to simply mention that there was research into aspirin and effects on various cancers, every time I tried to leave something out it became quite useless, or skewed the general NPOV in at least my feeling.
Where is the Wiki how-to page for footnotes? Because I agree with you that footnotes are cleaner and can make the section more succinct. (n/m, found that on your talk page : ) Gaviidae 09:14, 7 July 2006 (UTC)
I don't know of any particular source that has basic guidelines for the average Joe Schmuckenberger, although the 3rd-party reports that I ran across (CNN/BBC-style sites) always had a cautioning physician and sometimes the researchers of the particular study themselves cautioning against people reading about some study results and then chompin down aspirin like candy : )
I too think that there is so much out there that there could possibly be a link on the Aspirin page to an NSAIDs and Cancer page. I have also run across patients (mostly elderly who believed everything in Reader's Digest-- oh how I hate that publication!!) who were taking a full adult aspirin daily for their hearts (mind you I was not a physician at the time, only working in radiology doing GI studies and such), and I always had to remind them that they needed to ask their doctors first, and that the general aspirin recommendation for cardiovascular health is only a "child" dose, the 81mg chewies found at the drug store, not 325mg!
As for the COX-2 studies done by Merck (and I must be the only one who noticed that while Merck voluntarily removed their (otherwise great) drug, Pfizer continued to sell theirs and even later petitioned the FDA for a liquid or inhaled form of their COX-2 inhibitors?), either on this page or in one of the research papers I read (can't remember which, I'll check) it was mentioned possibly why COX-2 inhibitors increased thromboses etc. Maybe that section should be moved or copied to the NSAIDs/cancer section. It could be added to the current GI bleed warning in the beginning paragraph, along with the Wiki disclaimer "talk to your doc first" etc. The funny thing is, I seem to remember that there was some statistical reduction in polyps in the Merck study, but the results didn't count as the study was terminated early. It might also be apropo to add near the end of Cancer section the study you mention re adverse cardiovascular effects of non-aspirin NSAIDs-- that's a new one to me. Maybe a summary of current medical advice generally accepted now at the bottom? Gaviidae 07:48, 7 July 2006 (UTC)

Molecular Structure

I'd like to point out that the Lewis structure and the space filling structure on the Aspirin page have slightly different configs. The O and OH is swapped. --Russoc4 20:47, 12 September 2006 (UTC)

That doesn't matter, the carbon to which those groups are attached is non-chiral.83.147.180.185 12:44, 5 August 2007 (UTC)

Menstruating women?

Does ASA really cause increased menstrual bleeding? I can't find a reference for this, and actually it doesn't make much sense. The amount of menstrual bleeding should no be affected by any blood thinners, and (in fact) current menstruation is not even a contraindication for thrombolytic therapy. Maybe take out that line or a proper reference. Ksheka 12:43, 24 October 2006 (UTC)

This may actually make an interesting section. If anyone wants to take a shot at it, here are some references: [2] [3]

[4] [5] [6] Ksheka 12:51, 24 October 2006 (UTC)



Somebody---

I don't know anything about anything, but if somebody does, they might edit the line "Please note that children cannot tolerate as much aspirin per unit body weight as adults can, even when aspirin is indicated.".--Gtg207u 06:42, 3 January 2007 (UTC)

Fatal cases

I checked the references about the number of fatal cases of aspirin overdoses, and the vast majorit are suicide cases, which I added. This made me doubt the statement in the beginning about the several hunderd fatal overdoses occussing annualy, as this is hard to extrapolate from the 52 american cases, given the fact that suicide rates and preferred methods vary greatly across countries. Furthermore, I don't think intentional fatalities an unintentional ones should be counted together when discussing side effects of a drug. Unless someone adds a reference for the worldwide number of unintentional fatalities, I'm going to remove that sentence. 194.94.96.194 12:47, 2 February 2007 (UTC)

Done194.94.96.194 16:58, 16 February 2007 (UTC)

Picric Acid

Shouldn't this article mention picric acid, or be linked to the picric acid article, since pure ASA is crucial in the production of picric acid, and is quite often extracted by hobbyists or teachers for demonstrations? 65.103.218.97 23:03, 27 February 2007 (UTC)

Pronunciation

A pronunciation of acetylsalicylic acid would be nice. --Bookinvestor 04:54, 14 March 2007 (UTC)

I'm not very IPA-fluent—could someone check the following? IPA: [əˈsɛtlˌsæləˈsɪlɪk ˈæsɪd] Fvasconcellos 22:52, 15 March 2007 (UTC)
that is an acurate IPA transciption —The preceding unsigned comment was added by The Right Honourable (talkcontribs) 02:21, 17 March 2007 (UTC).

I have put the above IPA on the main page. Philiprogers 16:53, 8 April 2007 (UTC)

toxicity is not the right term

the section 'toxicity of low dose aspirin' should be called something like 'danger of low dose aspirin'The Right Honourable 02:32, 31 March 2007 (UTC)


introductory section

the paragraph about uses of low-dose aspirin should probably be moved to a new subsection or incorporated into some existing subsection dealing with uses. Right now the introductory section jumps into a discussion of very specialized discussion of use, which is really only one aspect of this rather broad article.

Question COX

Since platelets have no DNA, they are unable to synthesize new COX once aspirin has irreversibly inhibited the enzyme, an important difference with reversible inhibitors.

If Ibuprofen is a reversable inhibitor, how is that? if it affects both COX1 & 2, does it not affect COX1 the same way as aspirin? Even the answers further up don't quite get me. Gaviidae 12:53, 24 April 2007 (UTC)

Of course it does - but after a period of time, ibuprofen etc will dissociate from the COX, which will then start to work again. But aspirin stays permanently bound to the COX enzyme. In normal cells, the cell will just make more, working, COX, but a platelet cannot do this, so its COX is permanently inactivated. Dlh-stablelights 16:37, 15 June 2007 (UTC)

Oral asprin is near SPF 2 publication suggests this reduces UVA photoaging

oral aspirin is effective against UVA generated erythrema http://phot.allenpress.com/photonline/?request=get-document&doi=10.1562%2F0031-8655(2001)074%3C0587:UERCOM%3E2.0.CO%3B2 abstract at

It appears that oral aspirin it is about spf 2 at 250 mg 3 hours prior to UV thus there is the possibility then that time release asprin could halve the rate of photoaging

If you like put this on the main page

Aspirin is very clever

You can take it for rheumatic pain, sciatica, lumbago, headaches, period pain, dental pain and many other things. But how does it know which bit hurts and where it should go? :) -- SteveCrook 00:38, 4 June 2007 (UTC)

Readability

What is a 'centrally mediated vision disturbance'? Njál 22:31, 10 July 2007 (UTC)

Rasputin saves prince Alexei from Aspirin

I removed the paragraph about aspirin possibly given to Russian prince Alexei, who was saved from it by Rasputin. Nothing is known about Alexei taking aspirin. This is just another ridiculous story invented by Diarmuid Jeffreys in his poorly researched book "Aspirin: the remarkable story". In that book Jeffreys also perpetuates the myth that Eichengrun discovered aspirin. It is impossible to trust anything written in the book, which says that in 1856 Gerhardt examined the salicylic acid molecule under the microscope and saw the atoms; the hydroxyl group was rubbing off the stomach wall. If you do not believe me, it is on p47: "One of the many substances Gerhardt examined under his microscope was salicylic acid.[...] The first thing he noticed was that the acid's molecular structure was made of a central structure: a six-carbon benzene ring - with two attached components. These were a hydroxyl group of atoms and a carboxyl group of atoms. The hydroxyl set separated from the core when it rubbed against the stomach wall and it was this that caused the dreadful gastric irritation." Paul gene 00:43, 20 July 2007 (UTC)

My paperback copy of this book says "One of the many substances Gerhardt examined closely was salicylic acid.". I wonder if Paul is reading an early hardback edition that hadn't been reviewed thoroughly? Colin°Talk 11:34, 6 September 2007 (UTC)
I quoted a 2004 hardcover edition. Even if it does not have the rubbing hydroxyl groups thing, it is still complete nonsense. For example, Gerhard did not examine the acetylsalicilic acid closely, it was just one of about 20 examples in his paper, and he did not even bother purifying it. He did not "aim to replace the hydrogen atom of the hydroxyl group with an acetyl group" - at that time the notion of hydroxyl group did not exist, because the structural theory did not exist. "But it was a tricky process", says Jeffreys. No it was not, all he did was just to mix two compounds", etc, etc Paul gene 00:34, 8 September 2007 (UTC)
  • My goodness, that must have been a rather impressive microscope. I reverted your removal of unsourced claims, however, as I think you inadvertently deleted more than you intended to in a few instances. Zetawoof(ζ) 07:58, 20 July 2007 (UTC)

No it was not inadvertent. Rasputin had a source, so I commented regarding the dubiousness of that source. Separately from Rasputin I also deleted two statements, on which I had put facts tag in May. Since nobody since May sourced those statements, and I have no idea where they are coming from, I deleted them.Paul gene 01:15, 21 July 2007 (UTC)

Aspirin: the remarkable story

I'd like to counter a couple of accusations by Paul Gene about this book. Firstly, let me state that I am aware this is a book written by a journalist for a lay audience. As such it may contain over-simplifications, misunderstandings and mistakes (though the latter are common-enough in expert textbooks, especially early editions). The book has 277 pages of body-text, 32 small-type pages of "Notes and sources", 9 small-type pages of Bibliography and a 13 page index. It received a glowing review by the BMJ, awarded 4 stars out of 4. As a popular science book, it is a good read yet also contains sources for the text. However, I can appreciate that, as an expert, Paul was dissapointed when reading it.

  • The aspirin/Alexei/Rasputin account "is just another ridiculous story invented by Diarmuid Jeffreys in his poorly researched book". This is unfair. The Raputin story is contained within a footnote on page 121. Jeffreys states "It's very likely that to ease the pain the imperial doctors prescribed what, even then, was the world's most popular analgesic". I admit he does then get a bit carried away with the consequences and his book is criticised by some for these tangential stories. However, he does not claim Alexei definitely took aspirin. This story was not "invented" by Jeffreys. His source is Friend DG (1974). "Aspirin: the unique drug". Archives of surgery (Chicago, Ill. : 1960) 108 (6): 765–9. PMID 4597964. .
  • "Jeffreys also perpetuates the myth that Eichengrun discovered aspirin." I'd like to know how Paul has the confidence to call this a "myth". To do so implies that the argument has been settled and ridicules those who maintain an alternative theory. Jeffreys is aware of Sneader's paper (it is in his Bibliography) and appears to side with him. Jeffreys acknowledges that "The exact role Hoffman, Eichengrun and Dreser played in developing aspirin has been the matter of much debate" and also "Although there is considerable controversy over this issue, in my opinion the most reliable...". Jeffreys should be commended for informing his reader of the controversy and that certain aspects of history he relates are "in his opinion". Most journalists are taught to "assume authority" and simply tell the story how they see it.
  • You can read Sneader's paper here and the responses here. Sneader has written several papers on drug discovery and at least one book on the subject. As such, his views should not be lightly dismissed. Sneader responds to each of the letters and doesn't back down. Are there further articles that settle once-and-for-all that Sneader is wrong? If not, the current text is not NPOV. Paul's view may well be correct, but is only one POV. The current text of this article gives the impression that Sneader's paper has been dismissed and calls Eichengrün a "pretender to the title". Such language should not appear on WP except perhaps in a quotation.

I've already noted that the "microscope" gaff seems to have been corrected in later editions. I do wonder how one can honestly say "it is impossible to trust anything written in the book". That seems too harsh when some of the criticisms are just differences of opinion. History is not science; there are some "facts" we will never know for certain. Colin°Talk 13:45, 6 September 2007 (UTC)

Colin, you are right about some NPOV. Aspirin was one of the first articles I edited. I removed it, and I answer everything else later. Paul gene 11:41, 7 September 2007 (UTC)
  • It (the Jeffrey'sbook) received a glowing review by the BMJ. Interestingly, it is the first 2004 edition (the one that had the microscope gaffe) that received the glowing review in BMJ. Remember, the book reviews in BMJ are not peer-reviewed, so the BMJ respectability does not extend to them. I guess, some hack wrote it.
  • The "hack" was Boleslav L Lichterman, Centre for the History of Medicine, Russian Academy of Medical Sciences, Moscow, Russia. Some of his work is listed in Pubmed/Pubmed Central. Colin°Talk 15:19, 8 September 2007 (UTC)
A hack he is. From the Pubmed you can find out that his day job in an outfit called "Centre for the History of Medicine of Russian Academy of Medical Sciences" is expounding on topics like Medical ethics in Russia before the October revolution and after Russian revolution, and about Basic problems of medical ethics in Russia in a historical context, and about Conflict or harmony of Clinical research and the medical press in Russia. I would not be surprised if he did not read the book in full or even at all. More than 300 pages of English text must have been a lot for him. Paul gene 21:17, 8 September 2007 (UTC)
  • OK, let's presume that it was not Jeffreys but Friend DG who came up with the "Rasputin saves Alexei from aspirin" story. But look at what Jeffreys writes, "It's very likely [my emphasis] that" Alexei's doctors prescribed aspirin. And why is it likely? - because it "was the world's most popular analgesic". So, these are just speculations, and as such unverifiable and have no place in WP. The Nicholas II family doctor was killed together with the emperor's family in 1918, so it is unlikely that the story could come from him. If you can find the Friend DG paper, and see that he cites a memoir from somebody close to the Russian emperor, than I am all for including that fact into the Aspirin article. Paul gene 01:23, 8 September 2007 (UTC)
I agree, it is pure speculation and don't think there is any basis for it other than a hunch. Speculation (if attributed) can appear on WP, but WP:UNDUE suggests we shouldn't be reporting what is just a footnote after all... unless other authors have seized on this and it is now a commonly told story. Lets drop this one. Colin°Talk 15:19, 8 September 2007 (UTC)
  • "Jeffreys also perpetuates the myth that Eichengrun discovered aspirin." Before I started reading about aspirin, I had thought too that Sneader did a great thing when he uncovered the fascist conspiracy to promote "arian" Hoffman and forget the real father of aspirin "Jew" Eichengrun. However, as I looked through the available literature, I found that the prevailing point of view among historians and chemists is that neither Hoffman nor Eichengrun discovered aspirin. First of all, everybody, including Jeffreys agrees that Gerhardt was the first to synthesize aspirin. The next question is, who was the first to prepare pure aspirin. It was von Gilm, and he published a paper on the subject in the premier chemical journal of that time. Who established the structure of aspirin - Kraut and coworkers, and they published in the same journal. Now, if you ask who was the author of the aspirin's marketing campaign - the answer would be Eichengrun or Hoffman or Dreiser - but I cannot care less about that answer. I only covered the Eichengrun-Hoffman controversy because so much attention has been paid to it, so it had to be covered. Paul gene 01:46, 8 September 2007 (UTC)
It is more than just marketing. Did Hoffman not establish a new process for creating aspirin? If so, he deserves some credit. Some questions: Was that new technique necessary for producing large quantities in a pure form? Is that process still used today? I suspect, that even without the Bayer team, aspirin would have appeared around that time. In other words, it wasn't such a leap of genius. What do you think? Colin°Talk 15:19, 8 September 2007 (UTC)
Did Hoffman not establish a new process for creating aspirin? Was or wasn't it such a leap of genius.? The article says it all: "In 1897, Felix Hoffmann, a chemist at Friedrich Bayer & Co., obtained acetylsalicylic acid[7] by a reaction of salicylic acid and acetic anhydride;[8] that is, essentially repeating the Gilm/Kraut procedure but substituting acetic anhydride for acetyl chloride." So, he gets the credit he deserves. There is a discussion later in the article, as to whether his process was novel, and courts in GB and Germany said - no, and in the US - yes. No POV. Answering the questions, Was that new technique necessary for producing large quantities in a pure form? Is that process still used today?, would take a chemist and some original research. As for the marketing, product development and introduction of aspirin, the consensus appears to be to divide the credit among the three men - Eichengrün, Hoffmann and Dreser, because of the controversy and lack of established facts. My own opinion is that Eichengrün was probably the moving force behind aspirin, and Dreser also played an important role, but mostly because of his position. But this is my personal POV. Paul gene 21:39, 8 September 2007 (UTC)
  • You can read Sneader's paper here and the responses here. "Sneader has written several papers on drug discovery" and so did I, so my views should not be dismissed lightly ;). But lets consider the facts.
What is wrong with Sneader's paper? First of all, he discusses "discovery of aspirin", while it would be more correct to speak about "marketing of aspirin". He does not even mention Gerhard, whose role in the discovery of aspirin is recognized by everyone. He also conveniently forgets to mention that the US patent on aspirin has Hoffman's name as the inventor (and this is important since the US law unlike the law in many other countries requires that the real inventor be named, not just any representative of the company.) His article is all based on speculations around the time line of aspirin development, while he dismisses the only solid evidence - the note in Hoffman's notebook. He did not credit the previous research on the history of aspirin (at least three papers), which is a big no-no in science. Paul gene 02:24, 8 September 2007 (UTC)

Aspirin resistance

Aspirin is meant to reduce platelet activation to be of benefit in secondary prevention of strokes and heart attacks. If platelets remain activated (in laboratory assays), the result is termed "aspirin resistance". Until recently it was controversial whether this translates to poorer outcomes in patients. This meta-analysis indicates that people whose platelets remain activated are worse off.

Enter the routine ordering of aspirin resistance tests on everyone who has CVAs or MIs despite aspirin treatment. Hmm. JFW | T@lk 21:38, 13 August 2007 (UTC)

WP:RxCOTW

This article has been selected as the first Pharmacology Collaboration of the Week. The goal during this week is to raise this article to meet the featured article criteria, and nominate it on September 10, 2007 at WP:FAC.

Also, please visit WP:RxCOTW for other nominees for the next collaboration of the week. Dr. Cash 00:15, 5 September 2007 (UTC)

My first thoughts on quickly skimming this article are (1) it is massively under-referenced and (2) very listy. Any ideas on how to tackle the first? High-quality, reliable source suggestions welcome! :) Fvasconcellos (t·c) 01:17, 5 September 2007 (UTC)

Is it possible to get a better photo of aspirin crystals/powder? The one already there is way too...white.Jeff Dahl 02:11, 5 September 2007 (UTC)

Ugly! And what is so remarkable about aspirin crystals? You could make a shot of salt crystals and call them aspirin, and nobody would notice the difference. Let's remove the photo.Paul gene 09:38, 6 September 2007 (UTC)
I agree that the image is very hard to see. Furthermore, it's not really necessary for the article, although to me, salt & aspirin would be quite easy to tell the difference by looking at it (not sure about people without a scientific/chemistry background, though). If a better image could be taken, it **might** go better in the synthesis section, but it's not necessary, so I'll remove it for now. Dr. Cash 18:33, 7 September 2007 (UTC)

Origin of the name

Isn't aspirin a contraction of Acetylirte Spirsäure (acetylated spiræic acid), created by Bayer's Heinrich Dreser? What's this about it being derived from Raffaele Piria's surname? We must find a reference for this, or remove it. Fvasconcellos (t·c) 18:37, 5 September 2007 (UTC)

According to Bayer (and they should know that for sure) aspirin comes from acetylated spirsaure. All other versions of the word aspirin origins are nonsense and should be removed, whether there are references or not.Paul gene 09:34, 6 September 2007 (UTC)
From the book "Aspirin: The Remarkable Story of a Wonder Drug" by Diarmuid Jeffreys, 2004. ISBN 0-7475-7083-3, page 73:
On 23 January 1899, a memo circulated through Bayer's senior management addressing the thorny issue of what the new product should be called. Round robins of this sort were common and allowed everyone to have their say on a range of proposals. Because salicylic acid (as Karl Lowig had found out many years earlier) could be obtained from the meadowsweet plant, the document contained the suggestion that an abbreviation of the plant's Latin genus, Spiraea, should be put at the heart of the new brand name. The letter 'a' could be added at the front to acknowledge acetylation, and the letters 'in' could be tacked on to the end to make it easier to say — as was customary with many medicines of that time. It was noted that there was a drawback to this proposal because it might be suggestive of the word 'aspiration', which wouldn't have been an appropriate metaphor. An alternative could be the name 'euspirin'. When it came to him, Arthur Eichengrün, whose idea the final name probably was, wrote: 'I am in favour of Aspirin because "Eu" is generally used for improved taste and odour.' Carl Cuisberg, Felix Hoffman and Heinrich Dreser all signed without comment.[source: Bayer Leverkusen archives]
The book is a great read, BTW. Colin°Talk 11:24, 6 September 2007 (UTC)
I've removed the Piria line and reworded the remainder of the statement a bit. Thanks so much for the preceding paragraph, Colin; I've no doubt the book is a great read (I'm personally a Berton Roueché fan), although concerns have indeed been raised about its accuracy (and I'm not talking about Paul :) (OK, hadn't seen your notes above) Fvasconcellos (t·c) 13:51, 6 September 2007 (UTC)

History: a review

Here is a review of the History section. I've checked the facts against Jeffreys' book. I know Paul thinks this book is worthless, but it is what I've got to hand. As Fvasconcellos notes, this article is undercited. I don't mind whether this book is used as a source within this section or a better source found. It meets WP:RS, though I wouldn't dare to use it for medical or chemistry facts (see discussions on talk WP:MEDRS for where I've argued against the use of journalist's text for medical facts).

  • The Hippocrates sentence is confirmed on p15, but with a qualification: "Hyppocrates recommended the bark of the willow tree as an analgesic, although in this case it was as a remedy for the pains of childbirth and as a fever reducer." Perhaps our text should say "ease the pains of childbirth and reduce fever"?
  • On p11, a Sumerian tablet is mentioned, which lists willow along with numerous other remedies. Unfortunately, the tablet does not indicate what the remedy is for.
  • On p12, the Ebers Papyrus is noted to have three references to willow as "a general purpose tonic or as some kind of pain reliever and anti-inflammatory therapy". Jeffreys casts some doubt as to whether the remedies would have actually worked.
  • Lebanon, Assyria and the Cherokee aren't mentioned so I can't confirm the text here. On p28 he notes willow appears in sixth century Chinese medical texts (unclear indications) and some evidence of use by indigenous tribes in southern Africa and by Amerindians (neither had a written medical tradition, though).
  • Jeffreys devotes a whole chapter to Reverend Stone. The sentence in our text could be expanded into its own paragraph:
The Reverend Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, discovered in 1758 that the bark of the willow was effective in reducing a fever. Stone claims to have accidentally tasted willow bark and noted its bitterness was similar to the bark from cinchona, whose extract quinine was known to be effective in treating fever and agues (due to malaria). Stone was familiar with the doctrine of signatures, which held that the source of an illness (boggy grounds) and its cure (willow trees nearby) were often found together. Over then next five years, Stone experimented on 50 subjects and claimed near universal success. In 1763, he wrote of his discovery in a letter to George Parker, 2nd Earl of Macclesfield and president of the Royal Society, which was subsequently published in the society's Philosophical Transactions.[1]
  • Jeffreys book disagrees somewhat with the current text wrt to isolation of salicin. He claims (p38-9) the first person was Joseph Buchner, Professor of Pharmacy at Munich University. He obtained a tiny amount of "bitter-tasting yellow crystals" in 1828 and "christened it salicin (after salix, the Latin anme for willow)". Leroux is credited with refining the extraction procedure in 1829, and "obtained around 25 g of salicin crystals from one kilo of willow bark". In 1838, Raffaele Pira produced a more potent acid from the crystals, which he called "salicylic acid".
  • According to Jeffreys, the extraction from meadowsweet occurred in two stages: Swiss pharmacist Johann Pagenstecher extracted what he believed was the "therapeutic essence" and used it to treat pain. His report in a Swiss journal was discovered by the German Karl Jacob Lowig who obtained some of this tincture and transformed it into an acid, which he called "spirsaure" and tested its effects on reducing fever and pain. He had independently discovered salicylic acid.
  • Over pages 49-55, Jeffreys tells the story of Thomas John MacLagan and his experiments with salicin. He credits Maclagan with performing the first scientific study (of such compounds) and using a simple control process in his trial. The results were published: Maclagan, T. J., 'The treatment of acute rheumatism by salicin', Lancet, 4 March 1876. There followed a "flurry" of other papers documenting the success of salicylic acid. On his death in 1903, The Lancet proclaimed "Dr Maclagan would seem to have been the first to draw the attention of the medical profession to the use of salicin in modern days." I believe Maclagan deserves a mention at the end of this section.
  • Gerhardt's creation of ASA is covered in pages 46-7. Jeffreys' explanation of the chemistry might be shakey, but there are a couple of points worth adding. "he only managed to obtain a crude and impure version of the final substeance" and "Gerhardt found the whole procedure so lengthy and tedious that he decided to shelve it". Jeffreys also notes that Gerhardt's home town of Strasbourg has a memorial that recognises his place in the history of Aspirin.
  • The Gerhardt and von Gilm paragraphs contain footnotes that cite the original papers. As primary texts, they are unable to substantiate much of the discussion within these paragraphs. In addition, these papers are not available online or in English. As such, I suspect that WP editors haven't read them. I therefore strongly recommend the citations are ammeded with "as cited by ...." and a secondary source listed that is the true source of the information.
  • Jeffreys' book doesn't mention von Gilm nor Schröder, Prinzhorn and Kraut. A secondary source is required for this information. It would be nice if we could discover what von Gilm's forename was (begins with H).

That's as far as I've reviewed so far. Colin°Talk 18:43, 6 September 2007 (UTC)

    • Looks good. (Concise, I know :) I honestly have no reason to think the book's historical research would be objectionable, particularly since the facts surrounding aspirin's early history appear so...muddy. It has been mentioned, AFAIK, that Eichengrün's claims were dismissed because he was Jewish; apparently Jeffreys' book covers this? It would certainly warrant a mention here. Fvasconcellos (t·c) 22:48, 6 September 2007 (UTC)
      • By the way, Colin, I presume the Reverend Stone paragraph above is not a direct quote from the book; I think it should be added to the article. Fvasconcellos (t·c) 19:14, 7 September 2007 (UTC)
        • The paragraph is my wording, based on the whole chapter. I've left Paul a message on his talk page. Unless someone's got a better source, or Paul feels the book really is a worthless source, then I'll incorporate what I can into the article. That still leaves some unsourced text. I'll try to look at the rest of the history over the weekend. Colin°Talk 21:30, 7 September 2007 (UTC)
  • The Hippocrates sentence is confirmed on p15 "Hippocrate, le père de la médecine moderne, recommandait une tisane de feuilles de saule pour soulager les douleurs de l'enfantement et du jus d'écorce de peuplier pour certaines atteintes oculaires." see H. Lévesque1 and O. Lafont, L'aspirine à travers les siècles: Rappel historique, La Revue de Médecine Interne,Volume 21, Supplement 1, March 2000, Pages S8-S17 Paul gene 14:20, 8 September 2007 (UTC)
    • Hmmm. The above text describes a "herb tea of willow leaves to relieve the pains of the childbirth". The English abstract at PMID 10763200 says "chewing willow leaves for analgesia in childbirth". Was it tea or chewing that he recommended? Lots of sources for either on Google/PubMed. Several sources mention bark, bitter powders and reducing fever. I wonder if Hippocrates described two different treatments, using different parts of the tree, for fever and for pain in childbirth. What I've yet to find is a source that actually cites the Hippocratic corpus. Perhaps Lévesque/Lafont do, but their abstract disagrees with their text. I'd like to get this right as otherwise Wikipedia is just repeating all the cumulative mistakes of past writers. Colin°Talk 20:32, 12 September 2007 (UTC)
      • There is no inconsistency between the text of the Levesque article and its abstract in French: "Initialement utilisée sous forme de décoctions à base de feuilles ou d'écorce de saule par les Égyptiens et les Sumériens puis par Hippocrate, pour prévenir les douleurs de l'enfantement, et plus tard par le révérend Edward Stone (premier auteur à montrer scientifiquement son efficacité) pour traiter les fièvres, il fallut attendre le XIXe siècle pour découvrir le principe actif, et les caractéristiques de la salicine." However, in this quotation, Levescue refers to Mueller RL, Scheidt S. History of drugs for thrombotic disease. Discovery, development, and directions for the future. Circulation. 1994 Jan;89(1):432-49. This article is available free from the journal's website http://circ.ahajournals.org/cgi/reprint/89/1/432 and gives a very nice overview of the aspirin's history (better than Levescue's IMHO). It says: "The first recorded descriptions of therapeutic benefits of extracts of willow bark and other plant sources of salicylates were made by Hippocrates, the father of modern medicine, 2400 years ago.4 He recommended chewing willow leaves for analgesia in childbirth and the juice of the poplar tree for eye diseases." and refers to 4. Gross M, Greenberg LA. The Salicylates: A Critical Bibliographic Review. New Haven, Conn: Hillhouse Press; 1948:1-8. This appeared to be more reliable reference. However, in the 1856 edition of the Hippocrates' full works (available free at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge) there is only a single mention of willow (v 8, p 187): "Fumigation expulsive, capable aussi de faire sortir du sang hors de la matrice: mettre des feuilles de saule sur le feu et fumiger; on fera asseoir la femme et on la laissera jusqu’a ce que la vapeur entre dans matrice." Poplar bark (which also contains salicilin and other salycilates) is mentioned several times. More on this later. Paul gene 04:14, 13 September 2007 (UTC)
        • Oh the whole thing has got terribly confused. Mueller/Scheidt's language isn't very precise at times. Sentences that mention "willow bark" at the beginning and "willow leaves" at the end don't help clarify things. It also doesn't help that they say it is "the first recorded description" when Levescue and others mention Egyptians and Assyrians as being earlier (though I get the impression that it is difficult to always know precisely what they thought the medicine was good for). Finally, they credit Galen with the first antipyretic usage, not Hippocrates. My current gut feeling is that "chewing willow leaves for analgesia in childbirth" is correct and that willow bark has been wrongly associated with Hippocrates (at least as far as pain relief is concerned) due to either imprecise language or confusing things with Stone's usage of bark. Also, there are doubts about Hippocrates using willow for fever reduction.
Before mentioning poplar bark for eye diseases, do we know that the therapeutic effect (whatever that may be) was due to the salycilates? Colin°Talk 12:43, 13 September 2007 (UTC)
  • On p12, the Ebers Papyrus is noted to have three references to willow "Les Égyptiens connaissaient les propriétés antalgiques de la myrte et des feuilles de saule. Dans le papyrus Ebers [4], il existe une description très précise d'états inflammatoires répondant bien à la prise de tisanes à base de feuilles de saule (figure 1)." see Lévescue (2000) Paul gene 14:26, 8 September 2007 (UTC)
  • Gerhardt's creation of ASA is covered in pages 46-7. Jeffreys' explanation of the chemistry might be shakey, but there are a couple of points worth adding. "he only managed to obtain a crude and impure version of the final substeance" and "Gerhardt found the whole procedure so lengthy and tedious that he decided to shelve it". Sorry, but the last sentence is another example of Jeffreys' inventions. The procedure was very easy, and you can read it in the text of the Aspirin article. I also doubt very much that Jeffreys has any sources regarding Gerhardt "deciding to shelve it". By the way, according to the patent law and chemistry custom, it is often enough to prepare substantially pure (not pharmaceutically or analytically pure) compound to claim a priority for compound, and Gerhard, probably satisfies this requirement. Paul gene 02:47, 8 September 2007 (UTC)
One of your sources below confirms that Gerhardt's product wasn't pure, which I think we should mention. If it isn't pure enough to use as a safe medicine, then the improvements made by later chemists are significant. Colin°Talk 15:49, 8 September 2007 (UTC)
Agree, I just presumed that the fact that Gerhardt made only crude compound would be clear from the description. Paul gene 22:37, 8 September 2007 (UTC)
  • The Gerhardt and von Gilm paragraphs contain footnotes that cite the original papers. As primary texts, they are unable to substantiate much of the discussion within these paragraphs.
I disagree. See WP:PSTS: "Primary sources that have been published by a reliable source may be used in Wikipedia, but only with care, because it is easy to misuse them. For that reason, anyone—without specialist knowledge—who reads the primary source should be able to verify that the Wikipedia passage agrees with the primary source." "An article or section of an article that relies on a primary source should (1) only make descriptive claims, the accuracy of which is easily verifiable by any reasonable, educated person without specialist knowledge, and (2) make no analytic, synthetic, interpretive, explanatory, or evaluative claims". Which is exactly what I did, the corresponding paragraphs contain only short description of the relevant experiments and no comments or evaluation.
OK, on reviewing what I wrote I think the "much" isn't justified. However, the claim that "Gerhardt, was first to prepare acetylsalicylic acid" can't be taken from his paper (even if he himself boasts of it, he isn't unbiased and history (as often happens) might have shown him to be ignorant of some discovery elsewhere). Similarly "he did not pursue it further." probably can't come from the paper. In the second paragraph, "They were first to assign to it the correct structure" must come from a secondary source. Colin°Talk 15:49, 8 September 2007 (UTC)
In addition, these papers are not available online or in English. As such, I suspect that WP editors haven't read them.
Wrong, they are available online: see http://www3.interscience.wiley.com/cgi-bin/jissue/112322225 and http://www3.interscience.wiley.com/cgi-bin/jissue/112322853. Or you can order them free through an interlibrary loan. And knowledge of basic German is not a specialist knowledge, is it? And I did read them. Moreover, the articles are very old so they are not copyrighted. I could post images or PDFs somewhere but they are large. I can e-mail them too. The chemistry described in the papers does not go beyond the high school chemistry, and what is described in the Preparation chapter of the Aspirin article. Paul gene 03:18, 8 September 2007 (UTC)
Paul, I apologise for significantly underestimating you (though I didn't actually check/know who wrote those bits of the history section). WP is indeed fortunate to have such an expert. I can't read German. I think we should link to the online versions by using the DOI. Colin°Talk 15:49, 8 September 2007 (UTC)
secondary source listed... Here you go.
"The French chemist Charles Gerhardt was the first to synthesise acetylsalycilic acid in a crude form in 1853. In spite of the achievement of Gerhardt, the invention was ignored until 1859 when it was prepared again by von Gilm. Ten years later the German Karl Kraut found an improved synthetic method of making acetylsalicylic acid but, again, it was ignored…Arthur Eichengrun, who was responsible for pharmaceutical development, had an idea to develop much-needed version of salicylic acid with a better toxicity profile. This development was put in the hands of a 29-year-old chemist, Felix Hoffmann… In 1893 when Hoffmann searched the literature on salicylate derivatives he found the works of Gerhardt and Kraut. Hoffman developed an improved synthetic pathway to acetylsalycilic acid between 1893 and 1897, which he described in his laboratory notebook on 10 October 1897." T Hedner, The early clinical history of salicylates in rheumatology and pain , Clinical Rheumatology, v 17, no1, 1998, p17-25. Paul gene 03:43, 8 September 2007 (UTC)
"Like many legends, the aspirin story is not completely untrue. Hoffmann truly did synthesize acetylsalicylic acid. He may even given some to his father. Alas, Hoffmann found ASA not so much in the laboratory as in the library: It had been created in a crude form back in 1853 by a French chemis, Charles Frederic Gerhardt, and synthesized in a purer form sixteen years later by Karl Johann Kraut, a German. (Hoffmann's methos of making ASA, however, was an improvement over that of his predecessors.)" Charles C. Mann and Mark L. Plummer (1991). The aspirin wars: money, medicine, and 100 years of rampant competition. Boston, Mass: Harvard Business School Press, p. 25 Paul gene 03:55, 8 September 2007 (UTC)
Do you think we should remove the "gave to his father" legend (even Bayer use the word "legend")? Eichengrun seems to deserve the credit for starting the "lets improve on salicylic acid" task at Bayer. Colin°Talk 15:49, 8 September 2007 (UTC)
No we should not remove the legend; it is is an important part of the mass culture. Paul gene 22:37, 8 September 2007 (UTC) In my personal opinion Eichengrün would deserve the credit but there is no proof, except for his own claims and Sneader's time line speculations. Paul gene 23:52, 8 September 2007 (UTC)
Here is waht the best source (IMO) Mann (1991), p 25-36 tells us:
" Bayer's drug lab was split into two parts: a pharmaceutical section, which developed new drugs and was run by Arthur Eichengrün, a researcher with several successful products already under his belt; and a pharmacological section, which tested the drugs and was directed by Heinrich Dreser, a respected professor from the University of Bonn. The idea of a separate testing facility was Duisberg's. Fearful of incurring doctors' wrath by ship­ping drugs that didn't work, Duisberg wanted an additional check that would weed out all but the best remedies. Any drug developed by Eichengrün's lab would be passed on to Dreser's lab for his approval. As one of the new lab's first projects, Eichengrün chose to search for a version of salicylic acid with fewer side effects. ...
The lack of novelty did not discourage Eichengrün, who passed ASA to Dreser for testing. It was not a hit. Many doctors believed that salicylic acid had an "enfeebling action on the heart"; declaring that acetylsalicylic acid would necessarily share that enfeebling action, Dreser rejected ASA out of hand.* (Mann's footnote:* The reason for this erroneous belief is hard to ascertain, although it may have come from the then-common use of salicylic acid in massive doses to ease the pain and swelling of rheumatic fever. Given what in modern terms would be regarded as an overdose of salicylic acid, patients pant for breath and feel their hearts race. From this, doctors apparently concluded that salicylates can exhaust the heart.) For more than a year, what was destined to be the most successful drug ever invented sat on a shelf....
Acetylsalicylic acid remained among the drugs rejected by the pharmacological laboratory, until it was again brought to Dreser's attention late in 1898. How this occurred is a matter of dispute. Decades afterward, Eichengrün asserted rather angrily that it was only through his efforts that ASA was reconsidered by Dreser, and that he, Eichengrün, had believed from the start that ASA was the most promising medication yet developed by the lab. Dreser's contract gave him a veto over all clinical testing. His opposition to ASA, the irate Eichengrün wrote, had been a "death sentence" for the drug.
Vexed by Dreser's rejection, Eichengrün tested the new drug on himself. When his heart was not poisoned, he decided to examine it further. While ASA sat in Dreser's lab, Eichengrün surreptitiously passed it to doctors in Berlin, who administered it to their patients. ASA not only eased the discomfort of fevers and aching joints, they learned, it also soothed headaches. Significantly, it had many fewer side effects than salicylic acid or any of the variants of salicylic acid on pharmacy shelves.
One of the doctors, Felix Goldmann, was Bayer's representative in Berlin, the nation's capital, cultural center, and biggest city. He delivered an enthusiastic report on ASA to the company's management. Asked his opinion of Goldmann's memo, Dreser growled: "This is the usual Berlin bragging; the product has no value." At this point, according to Eichengrün, Duisberg himself came to the rescue. He insisted that tests be conducted by an outside pharmacologist. The results were glowing. Finally acceding, Dreser wrote a scientific paper extolling ASA. In it he neglected to mention Hoffmann and Eichengrün." Paul gene 17:34, 9 September 2007 (UTC)


"Même si son nom est toujours resté dans l'ombre le premier à avoir synthétisé l'aspirine est un chimiste français de renom [5], le pharmacien Charles-Frédéric Gerhardt (1816-1856), qui fut un temps professeur à l'École supérieure de pharmacie de Strasbourg, dont le rôle, dans le développement de la théorie atomique fut considérable et qui introduisit la notion de série homologue en chimie [28]. Présentés en mai et juin 1852, puis publiés l'année suivante en français [29] et en allemand [30], ses travaux portant sur les anhydrides d'acide, consistaient à faire réagir le sel de sodium d'un premier acide carboxylique avec le chlorure d'acyle provenant de l'halogénation d'un second acide organique. Il eut l'idée de faire réagir le salicylate de sodium sur le chlorure d'acétyle. Il considéra que la substance blanche qu'il avait isolée était l'anhydre mixte de l'acide salicylique et de l'acide acétique. Il la nomma « acide acéto-salicylique ». En fait, c'est l'acide acétylsalicylique qu'il avait obtenu, sans toutefois l'identifier [31] ! Ce n'est qu'en 1859 que l'acide acétylsalicylique fut consciemment synthétisé par H. von Gilm, par action de l'acide salicylique sur le chlorure d'acétyle [31], et en 1869 que ce produit fut identifié à celui que Gerhardt avait synthétisé seize ans plus tôt [32]. Il ne s'agissait alors que de chimie organique pure, sans visée thérapeutique particulière." H. Lévesque1 and O. Lafont, L'aspirine à travers les siècles: Rappel historique, La Revue de Médecine Interne,Volume 21, Supplement 1, March 2000, Pages S8-S17 (sorry for the typos) Paul gene 04:20, 8 September 2007 (UTC) I just only corrected the typos in the above quotation and did not change anything else, I hope it is OK with you. Paul gene 15:21, 8 September 2007 (UTC) Lévesque (2000) further goes on: "En 1895, décidant de s'intéresser aux produits pharmaceutiques, cette société fait appel au pharmacologue Heinrich Dreser et au docteur Arthur Eichengrün et engage une dizaine de chimistes dont le pharmacien Felix Hoffmann dont l'un des sujets de recherche proposés portait sur l'élaboration d'un dérivé de l'acide acétylsalicylique moins toxique. La légende suggère que le père de ce jeune chimiste souffrant d'un rhumatisme inflammatoire, calmé par l'acide salicylique, mais le tolérant mal sur le plan digestif, aurait demandé à son fils de lui trouver un remède miracle. Ce dernier se plongeant dans les travaux de Gerhardt et de Kraut et adaptant peut-être la technique imaginée par le Russe Marcellus Nencki (1847-1901), redécouvrit l'acide acétylsalicylique (figure I). Felix Hoffmann proposa donc l'utilisation de cette molécule qui fut initialement refusée par Dreser, du fait d'une possible cardiotoxicité sur la grenouille." Paul gene 15:46, 8 September 2007 (UTC)

I have another 2 refs, let me know if you need quations from them. Paul gene 04:26, 8 September 2007 (UTC)

  • Jeffreys' book doesn't mention von Gilm nor Schröder, Prinzhorn and Kraut. A secondary source is required for this information. It would be nice if we could discover what von Gilm's forename was (begins with H). Well, did I not tell you that Jeffreys' book is poorly sourced? Von Gilm's name - only H is in the original, sorry. Paul gene 04:26, 8 September 2007 (UTC)
Shame about the H. Including forenames is the sort of reader-friendly thing we should do. It is one good thing about a pop-science source compared to a medical paper :-) Colin°Talk 15:49, 8 September 2007 (UTC)
  • Jeffreys book disagrees somewhat with the current text wrt to isolation of salicin. "However, the earliest attempts to isolate an active principle from willow bark were made by the Italians Fontana and Brugnatelli. Between 1826 and 1829, they managed to isolate small amounts of the glycoside compound salicin [4]. German and French scientists were also trying to isolate an active principle from natural sources and, in 1828, Buchner in Munich also isolated salicin [4]. A year later, the Frenchman Leroux managed to do the same task and also demonstrated its antipyretic activity [5]. Some years later, in 1833, Merck in Darmstadt made the same discovery and isolated salicin from willow bark [5]." see Hedner (1998) Paul gene 12:15, 8 September 2007 (UTC)
  • According to Jeffreys, the extraction from meadowsweet occurred in two stages

"Other early achievements in pharmaceutical chemistry were made by the Swiss pharmacist Pagenstecher who, in 1831, distilled salicylaldehyde from the meadowsweet or the queen of the meadow plant (Spiraea ulmaria, now Filipendula ulmaria) [6]. A further important step was taken by the Swiss chemist Lowing in 1835 [5], who became the first to prepare salicylic acid. In Paris, salicylic acid was isolated by Piria in 1838 from the willow bark glycoside salicin [5] and a year later Dumas showed that Lowing's and Piria's compounds were identical. Both scientists had prepared salicylic acid, one working with salicin from willow bark, and the other working with salicylaldehyde from meadowsweet [5]. In the New World, the American William Procter and the Frenchman Auguste Cahours were working with wintergreen (Gaultheria procumbens and G. hispudula), which was an old folk remedy for 'aguish disorders' [6]. In 1843 they managed to isolate methyl salicylate and in the following years Cahours described how to hydrolyse methyl salicylate to salicylic acid [6]." see Hedner (1998) Paul gene 12:25, 8 September 2007 (UTC)

  • Over pages 49-55, Jeffreys tells the story of Thomas John MacLagan and his experiments with salicin. He credits Maclagan with performing the first scientific study (of such compounds) and using a simple control process in his trial. "Si les caractéristiques et les modalités d'extraction furent plus ou moins rapidement précisées, il était important de vérifier que cette salicine jouissait réellement des propriétés fébrifuges revendiquées soixante ans auparavant par le clergyman anglais Edward Stone. Nous avons vu les réserves émises par plusieurs auteurs tels Trousseau [17] ou Foy [18], cependant un certain nombre d'expériences tentées dans les hôpitaux parisiens furent concluantes et le célèbre médecin Magendie pouvait affirmer qu'à la posologie de 1 g par jour en trois prises elle coupait les fièvres du jour au lendemain et ceci quel que soit leur type. De fait, dans les traités de médecine et de thérapeutique de la tin du XIX siècle, l'efficacité de la salicine ne semble plus discutée : l'accord est unanime aujourd'hui pour reconnaître l'efficacité absolue de la médication salicylée [24], le salicylate de soude employé depuis bientôt vingt ans n'a plus à faire ses preuves [25]. En 1874, un médecin de Dundee, T.J. Mac Lagan, également influencé par la théorie des signatures, fit les mêmes constatations que le révérend Stone et décida de rechercher un remède contre le rhumatisme articulaire aigu parmi les Salicaceae, connues pour contenir de la salicine. Après avoir pris lui-même 5 puis 10 puis 30 grains (envi-mn 2 g) de salicine, sans ressentir le moindre inconvénient, il décida de donner à un patient, « porteur d'un rhumatisme articulaire très avancé », 12 grains de salicine toutes les trois heures. Les résultats dépassèrent tout ce que je pouvais espérer, avec notamment une chute de la fièvre etc une diminution de la douleur et de l'enflure des articulations. Il observa alors des résultats similaires chez huit autres patients rhumatisants (quatre formes aiguës, trois subaiguës et une chronique) [26]. Quelques semaines plus tard, dans une lettre réponse au Lancet, le docteur Ensor, exerçant au cap de Bonne-Espérance en Afrique du Sud, signalait que les Hottentots, peuplade primitive, connaissaient l'effet antirhumatismal du saule depuis de nombreuses années. En effet, dans sa lettre pleine d'humour, il signale l'observation d'une femme souffrant, d'après ses termes, de la plus féroce attaque de rhumatisme articulaire aigu qu'il ait jamais vu, à laquelle il proposa le traitement habituel à cette époque (poudre de Dover et calomel). Revoyant la malade deux mois plus tard, totalement asymptomatique, il se félicita de son traitement jusqu'à ce que cette dernière, lui expliquant que son traitement ayant été un échec total, elle avait consulté un vieux berger hottentot. qui avait préconisé une décoction de feuilles de saule après en avoir pris pendant plusieurs jours, les douleurs commencèrent à diminuer et finalement disparurent complètement [in 5]" see Lévescue (2000) Paul gene 14:57, 8 September 2007 (UTC)
Thanks for taking the time to dig out and type up all this. I've not got time to digest all the above at the moment. The question is: are you going to incorporate these sources and extra facts into the text or shall I? Colin°Talk 15:49, 8 September 2007 (UTC)
No problem, I used OCR software;), and I have had the PDF files of the references for a long time. Please incorporate the references into the article as you see fit; thank you for your help. Paul gene 23:52, 8 September 2007 (UTC)

"The mechanism of action of aspirin"

Free full text of Vane's short 2003 review. A very interesting read. Fvasconcellos (t·c) 21:17, 9 September 2007 (UTC)

Yes, it is very interesting. I suggest putting a link to this review at an appropriate place in the article. Dirac66 02:08, 16 September 2007 (UTC)

Done. Dirac66 (talk) 17:13, 31 December 2007 (UTC)

Breast cancer risk

This news link claims "A new study has found that aspirin use can cut the risk of breast cancer by almost 25 percent." The study is PMID 17698973, and such a lofty claim could use confirmation. Full text, anyone? Fvasconcellos (t·c) 21:54, 9 September 2007 (UTC)

Here's an exact quote from the discussion section of the paper (PMID 17698973) and is repeated in the abstract:
"We observed no association between aspirin use or total NSAID use and breast cancer risk among the female members of the Multiethnic Cohort study, but we did observe a protective effect of other NSAID use among current users..."
So the "protective effects" only show up with non-aspirin NSAIDs. Funny how the news media grabs on to the story they want to see rather than what is actually there. Jeff Dahl 17:47, 13 September 2007 (UTC)
Indeed. Thanks for finding this—I could have at least read the abstract :P Fvasconcellos (t·c) 22:38, 13 September 2007 (UTC)

Yet another myth - Hippocrates prescribed willow bark to his patients for pain relief

I copied the discussion on Hippocrates from above for convenience.Paul gene 01:02, 15 September 2007 (UTC)

  • The Hippocrates sentence is confirmed on p15, but with a qualification: "Hyppocrates recommended the bark of the willow tree as an analgesic, although in this case it was as a remedy for the pains of childbirth and as a fever reducer." Perhaps our text should say "ease the pains of childbirth and reduce fever"?

"Hippocrate, le père de la médecine moderne, recommandait une tisane de feuilles de saule pour soulager les douleurs de l'enfantement et du jus d'écorce de peuplier pour certaines atteintes oculaires." see H. Lévesque1 and O. Lafont, L'aspirine à travers les siècles: Rappel historique, La Revue de Médecine Interne,Volume 21, Supplement 1, March 2000, Pages S8-S17 Paul gene 14:20, 8 September 2007 (UTC)

    • Hmmm. The above text describes a "herb tea of willow leaves to relieve the pains of the childbirth". The English abstract at PMID 10763200 says "chewing willow leaves for analgesia in childbirth". Was it tea or chewing that he recommended? Lots of sources for either on Google/PubMed. Several sources mention bark, bitter powders and reducing fever. I wonder if Hippocrates described two different treatments, using different parts of the tree, for fever and for pain in childbirth. What I've yet to find is a source that actually cites the Hippocratic corpus. Perhaps Lévesque/Lafont do, but their abstract disagrees with their text. I'd like to get this right as otherwise Wikipedia is just repeating all the cumulative mistakes of past writers. Colin°Talk 20:32, 12 September 2007 (UTC)
      • There is no inconsistency between the text of the Levesque article and its abstract in French: "Initialement utilisée sous forme de décoctions à base de feuilles ou d'écorce de saule par les Égyptiens et les Sumériens puis par Hippocrate, pour prévenir les douleurs de l'enfantement, et plus tard par le révérend Edward Stone (premier auteur à montrer scientifiquement son efficacité) pour traiter les fièvres, il fallut attendre le XIXe siècle pour découvrir le principe actif, et les caractéristiques de la salicine." However, in this quotation, Levescue refers to Mueller RL, Scheidt S. History of drugs for thrombotic disease. Discovery, development, and directions for the future. Circulation. 1994 Jan;89(1):432-49. This article is available free from the journal's website http://circ.ahajournals.org/cgi/reprint/89/1/432 and gives a very nice overview of the aspirin's history (better than Levescue's IMHO). It says: "The first recorded descriptions of therapeutic benefits of extracts of willow bark and other plant sources of salicylates were made by Hippocrates, the father of modern medicine, 2400 years ago.4 He recommended chewing willow leaves for analgesia in childbirth and the juice of the poplar tree for eye diseases." and refers to 4. Gross M, Greenberg LA. The Salicylates: A Critical Bibliographic Review. New Haven, Conn: Hillhouse Press; 1948:1-8. This appeared to be more reliable reference. However, in the 1856 edition of the Hippocrates' full works (available free at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge) there is only a single mention of willow (v 8, p 187): "Fumigation expulsive, capable aussi de faire sortir du sang hors de la matrice: mettre des feuilles de saule sur le feu et fumiger; on fera asseoir la femme et on la laissera jusqu’a ce que la vapeur entre dans matrice." Poplar bark (which also contains salicilin and other salycilates) is mentioned several times. More on this later. Paul gene 04:14, 13 September 2007 (UTC)
        • Oh the whole thing has got terribly confused. Mueller/Scheidt's language isn't very precise at times. Sentences that mention "willow bark" at the beginning and "willow leaves" at the end don't help clarify things. It also doesn't help that they say it is "the first recorded description" when Levescue and others mention Egyptians and Assyrians as being earlier (though I get the impression that it is difficult to always know precisely what they thought the medicine was good for). Finally, they credit Galen with the first antipyretic usage, not Hippocrates. My current gut feeling is that "chewing willow leaves for analgesia in childbirth" is correct and that willow bark has been wrongly associated with Hippocrates (at least as far as pain relief is concerned) due to either imprecise language or confusing things with Stone's usage of bark. Also, there are doubts about Hippocrates using willow for fever reduction.
Before mentioning poplar bark for eye diseases, do we know that the therapeutic effect (whatever that may be) was due to the salycilates? Colin°Talk 12:43, 13 September 2007 (UTC)
  • First, background. There have been no printed translations to English of the parts of Hippocratic Corpus, namely Diseases of Women and Nature of Women, that mention the use of willow and poplar. The most complete and authoritative translation of the Corpus to a contemporary European language is Oeuvre complètes d'Hippocrate. Ed. Emile Littré. 10 vols. Paris, J.B.Bailliére, 1839-1861, mentioned above and now freely available online at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge. An English translation from Greek of the part I of The Diseases of Women done by Kathleen Whiteley as a part of her MA work at the University of South Africa is freely available online at http://etd.unisa.ac.za/ETD-db/theses/available/etd-06142004-162341/unrestricted/04dissertation.pdf. Whitely tries to make the text more understandable for the contemporary reader but this does not always work.
The above passage about willow leaves fumigation (v 8, p187) Whiteley translates as "Fragrant medication for expelling the foetus or placenta, also enabling the woman to expel blood from the belly: put willow leaves on a fire, fumigate, and make the woman sit until the smoke goes into the womb."
Poplar
v 8, p 183. Littré: "Autre moyen expulsif ... bien neuf cocons rèsineux du peuplier de Crète, piler, boire dans du vin." Whiteley: "Another means of expelling the placenta: ... let her drink nine seeds from the black poplar of Crete ground into wine." Here I do not know how neuf cocons resineux can turn into nine seeds.
v 8, p 229 Littré: "Pour l’argémon: larme de peuplier, lait de femme, mêler et s’en servir." Whiteley: "For albugo (A white speck on the eye - LSJ) you must use black poplar sap mixed with breast milk." Paul gene 01:02, 15 September 2007 (UTC)
v 7 p349 Littré: "chasse le chorion ...Autre: prenez des noeuds résineux, au nombre de neuf, du peuplier de Crète (populus gracia), pilez-les et faites-les boire dans du vin, c'est un moyen qui favorise aussi la délivrance quand l'accouchement est laborieux." (Use http://babelfish.altavista.com/tr for a quick and dirty translation to English.)
v 8 p357 as a part of multicomponent concoction "pour la matrice".
The bottom line is, there is no indication in Hippocratic Corpus of any use of willow as a pain medication or for inflammation. The Corpus recommended willow leaves fumigation or poplar parts in vine for expelling fetus, placenta or chorion, or helping with difficult delivery. Poplar sap in breast milk could be used for an eye disease. Paul gene 01:53, 15 September 2007 (UTC)

Move salicylic acid to a separate page?

As has been pointed above, aspirin has a different mechanism of action than salicylic acid, which is related to its acetyl group. Should these two compounds share the same page? Paul gene 02:07, 22 September 2007 (UTC)

Erm, they don't? Fvasconcellos (t·c) 02:14, 22 September 2007 (UTC)
Here is what this (ASPIRIN) article says: " Aspirin acts as an acetylating agent where an acetyl group is covalently attached to a serine residue in the active site of the COX enzyme." And there is no acetyl group in salicylic acid. Also see: http://en.wikipedia.org/wiki/Talk:Aspirin#Action_of_salicylic_acid.3F It is good that salicylic acid has its own page, so we can move all the ancient history there. Paul gene 14:24, 22 September 2007 (UTC)

Here's some lay comments/questions:

  • Any popular or medical article discussing the history of aspirin includes the history of salicylates. We'd have to have pretty good NOR reasons for excluding them.
  • Aspirin has multiple therapeutic uses, not all of which share the same mechanism of action. The article perhaps doesn't make this clear. For example, the last sentence hints that reducing inflammation is a property of the salicylates. The principle pain-relief mechanism seems to be aspirin-specific (if I interpret this discussion correctly) but if the salicylates have pain relief / fever reduction properties, does aspirin also share those properties? In other words, does it have two mechanisms for pain relief and/or fever reduction?
  • Aspirin shares some side-effects with salicylic acid. Are these due to related chemistry?

The article should be clearer about the differences with salicylic acid, both medically and in its actions. The salicylic acid article could clearly be expanded. Colin°Talk 15:24, 22 September 2007 (UTC)

These all are very good points. I do not really know anything about the aspirin pharmacokinetics, e.g. how much of it is decomposed in the body to salicylic acid. I am still not sure how relevant the history of salicylates is to the history of aspirin. Would the history of khat be relevant in bupropion or, even closer, diethylpropion (Tenuate) article? (Diethylpropion is partially metabolized to cathinone, the active principle of khat.) On the other hand, histories of fluoxetine and sertraline do begin with the histories of structurally related compounds. The said fluoxetine and sertraline precursors, however, do not have their own pages. Paul gene 11:22, 23 September 2007 (UTC)
And I do not suggest excluding the history of salycilates, I suggest linking to it. The history of aspirin could begin with "Salicylates have been used since antiquity [link to the moved history in the salicylic acid article]. The French chemist Charles Frederic Gerhardt ....." Then, an introductory sentence would be needed after Kraut and before Hoffmann about the increased medicinal use of salicylic acid in 1870-1900, and how Bayer began working on pro-drugs of salicylic acid to decrease the gastrointestinal side effects. Paul gene 11:37, 23 September 2007 (UTC)

Coughing

Coughing says coughing is a side affect of aspirin? Is this correct on this page? (and if so, why does it cause coughing?) Caffm8 (talk) 19:31, 10 December 2007 (UTC)

History - initial side-effects

Initially aspirin had many problems - shouldn't this be included in the history section? See here, page 456/7. Thoughts? Malick78 (talk) 21:14, 20 January 2008 (UTC)

Reyes syndrome

am i incorrect to say that aspirin is contraindicated in children under the age of 16 according to the BNF not under 12 as stated on this page?

Liamoh (talk) 11:17, 13 March 2008 (UTC)

You are correct (BNF 53 (2007)). Fixed. Thanks for pointing it out. - Neparis (talk) 14:48, 13 March 2008 (UTC)

Aspirin in fiction?

I know it's there, i.e. Doctor Who where he says a tablet of aspirin could kill him.

DarkestMoonlight (talk) 15:54, 18 March 2008 (UTC)

Mechanism of action of aspirin article?

An editor has suggested during this article's peer review that the section about aspirin's mechanism of action could potentially be split into it's own article. Personally, I think that with a little more content and a few more sources, this section could indeed stand as it's own article, which would help to shorten Aspirin somewhat by just using a summary. What do other editors think about this idea? CrazyChemGuy (talk) 21:10, 15 April 2008 (UTC)

History section

Paul gene reverted the update of the history section with the explanation: "Replaced unbalanced version of history based on Bayer promotions with the conventional one. Discuss before reverting." ' That version was the intro from history of aspirin, which I think is a fairly balanced and concise overview of the history. It is not based on Bayer promotions, and only coincides with them to the extent that they are accurate. It mentions Bayer in only two sentences, and notes that before academic work in synthesizing aspirin existed before Bayer turned the drug into a world-wide commercial success. Here is that version:



The history of aspirin and the medical use of it and related substances stretches back to antiquity, though pure aspirin (acetylsalicylic acid or ASA) has only been manufactured and marketed since 1899. Medicines made from willow and other salicylate-rich plants date back at least to 3000 BC, and were part of the pharmacopoeia of Western medicine in Classical antiquity and the Middle Ages. Willow bark extract became recognized for its specific effects on fever, pain and inflammation in the mid-eighteenth century. By the nineteenth century pharmacists were experimenting with and prescribing a variety of chemicals related to salicylic acid, the active component of willow extract.

In 1853, chemist Charles Frédéric Gerhardt reacted acetyl chloride with sodium salicylate to produce acetylsalicylic acid for the first time; in the second half of the nineteenth century, other academic chemists established the compound's chemical structure and devised more efficient methods of synthesis. In 1897, scientists at the drug and dye firm Bayer began investigating acetylsalicylic acid as a less-irritating replacement for standard common salicylate medicines. By 1899, Bayer had dubbed this drug Aspirin and was selling it around the world. Aspirin's popularity grew over the first half of the twentieth century, spurred by its effectiveness in the wake of Spanish flu pandemic of 1918, and aspirin's profitability led to fierce competition and the proliferation of aspirin brands and products.

Aspirin's popularity declined after the development of acetaminophen in 1956 and ibuprofen in 1962. In the 1960s and 1970s, John Vane and others discovered the basic mechanism of aspirin's effects, while clinical trials and other studies from the 1960s to the 1980s established aspirin's efficacy as an anti-clotting agent that reduces the risk of clotting diseases. Aspirin sales revived considerably in the last decades of the twentieth century, and remain strong in the twenty-first, thanks to widespread use as a preventive treatment for heart attacks and strokes.


The earlier version was, in my view, extremely unbalanced, focusing almost solely on the synthesis of aspirin and neglecting its broader social, commercial and clinical history. If there are specific suggestions for how the above version is improperly balanced, I'm eager to hear them so that the history of aspirin intro can be improved. I'm resubstituting this material here; let's work to make it an acceptable and broad historical overview.--ragesoss (talk) 18:12, 17 April 2008 (UTC)

The problem with the version of Aspirin history Ragesoss is suggesting, is that unfortunately it is based on Bayer promotional materials and more than 100-year-old science. Point-by-point
  • Why mention that Bayer synthesized pure ASA? - because it is in Bayer promotion materials that Bayer was first to do that. Neither German authorities nor the UK courts of the time found any merits in this claim (the US court disagreed). It is generally accepted among chemists that von Gilm and Kraut prepared pure acetylsalycilic acid earlier.
  • Aspirin is less-irritating than salicylic acid or sodium salicylate. - Also a century-old Bayer claim. Is there any contemporary evidence that aspirin is less-irritating than salicylic acid or sodium salicylate?
  • Should other salicylates be mentioned in such detail? Bayer scientists a century ago believed aspirin to be a prodrug of salicylic acid. It is not so, and the mechanism of action of aspirin is different and is due to its acetyl group.
  • It is unfair to chemists to exclude the history of aspirin preparation and determination of its structure in favor of commercial details. Paul Gene (talk) 23:04, 17 April 2008 (UTC)
I argued much the same points in September of 2007 (see the Discussion History of that time) and seem to convince the other editors. Thus, you changed a discussed at length and accepted version of the article. Paul Gene (talk) 23:12, 17 April 2008 (UTC)
Paul gene, thanks. The secondary sources I've found (in particular, Aspirin Wars by Mann and Plummer and Aspirin by Jeffreys) both claim that aspirin is less irritating. Is there a more reliable source that claims the contrary? Neither of these sources is particularly kind to Bayer in general (and both side pretty much accept Eichengrun's account of the Bayer synthesis, contra Bayer's standard legend). Neither mentions von Gilm; are there secondary sources we can use that confirm vol Gilm's synthesis of pure ASA? If that is in fact widely accepted, then that section can be reworded; the key thing that Bayer did, after all, was effectively build aspirin's reputation (as a less-irritating salicylate and as a clinically effective drug) and market it effectively, and whether or not they were the first to obtain pure ASA is a secondary concern. I will try to rework it to address your concerns; a reliable secondary source on von Gilm and non-irritation would be greatly appreciated.--ragesoss (talk) 00:17, 18 April 2008 (UTC)
I've revised the second paragraph; hopefully it's more to your liking. It no longer mentions purity, which you are right about being beside the point, and it mentions Gerhardt's work specifically. It also presents the "less-irritating" bit from the perspective of the Bayer scientists, without definitively claiming that aspirin is in fact less irritating. The amount of coverage of salicylates is appropriate, in my view; both of the history of aspirin books I mentioned devote a substantial portion of their coverage to the prehistory of aspirin, as do most other sources I've seen. As for discussion of the business aspects short-changing the chemists, both aspects need to be covered (as well as the research on mechanism and clinical effectiveness, both of which are also crucial aspects of aspirin's history). The social side of a drug is no less significant than the chemical side, especially a drug that has been used in as many ways as aspirin over such a long period.--ragesoss (talk) 00:34, 18 April 2008 (UTC)
Thank you, you revision is very reasonable. Salicylates should be mentioned to provide the background as to why Bayer was looking for their replacement. I just think that it is disproportionately long in this version of the article. The aspirin history is shrouded in many myths and you want to be careful not to trust all the claims in the secondary sources. Jeffries book is particularly full of inventions. Even other, more academic sources, make mistakes. For example, Hippocratic Corpus has no mentions of willow concoctions as a pain killer. This claim appears first in a 1930s review on antique medicine, but I was not able to obtain that source. Paul Gene (talk) 10:37, 18 April 2008 (UTC)

Survey

WP:Good article usage is a survey of the language and style of Wikipedia editors in articles being reviewed for Good article nomination. It will help make the experience of writing Good Articles as non-threatening and satisfying as possible if all the participating editors would take a moment to answer a few questions for us, in this section please. The survey will end on April 30.

  • Would you like any additional feedback on the writing style in this article?


  • If you write a lot outside of Wikipedia, what kind of writing do you do?


  • Is your writing style influenced by any particular WikiProject or other group on Wikipedia?


At any point during this review, let us know if we recommend any edits, including markup, punctuation and language, that you feel don't fit with your writing style. Thanks for your time. - Dan Dank55 (talk)(mistakes) 04:12, 21 April 2008 (UTC)

GA Review

This review is transcluded from Talk:Aspirin/GA1. The edit link for this section can be used to add comments to the review.

The article is fairly close to meeting the GA criteria, but needs a little bit of work to bring it up to standards:

  • There are several citation issues in the article. First, there's a 'citation needed' tag that needs to be addressed. I've also seen several sections with uncited or poorly cited material, mostly in the history section, but also in a few other places.
YesYCitation issues appear to have been adressed.CrazyChemGuy (talk) 22:54, 2 May 2008 (UTC)
  • The prose could use a bit of a cleanup. I would recommend a good, thorough copyedit. Some material looks a bit too technical, and almost looks like some information from the abstracts of scientific articles was just copied directly into the article (e.g. 'adverse effects'). That section should have a summary at the beginning of the section, instead of just going right into subsections. Try to tie the information together instead of just listing it. Some sentences need to be corrected for grammar and rephrased.
  • There's some manual of style issues, so I would recommend someone with experience in that area to copyedit the article. Look at wikilinking (only full dates should be linked, not years and not month years). Why is rat wikilinked? There doesn't seem to be context for this. The placement of reference citations in sentences should also be examined -- citations should be placed immediately after the sentence(s) being cited, immediately after the punctuation with no space between (like this.[2] not like this. [3]). There's some references listed which only have a single external link with no author, title, publisher, date of publication, date URL retrieved, included in the citation.
  • I would promote the mechanism of action section; this seems to be a bit more important than some of the other sections. Probably should fall right after 'therapeutic uses'.
YesYSection has been moved. CrazyChemGuy (talk) 19:02, 30 April 2008 (UTC)
  • WP:MEDMOS does not advocate having a 'dosage' section; we have to be very careful with this as we don't want to look like we're providing actual medical advice. This section could be removed from the article.
YesYDosage information was removed from the section; section should now comply with WP:MEDMOSCrazyChemGuy (talk) 19:02, 30 April 2008 (UTC)
  • 'Contraindications' is just a bulleted list. While generally well cited (except for one point), it should ideally be converted to prose and there should be more information to tie this section together better. As it's written, it looks like it belongs in the drug information brochure by the manufacturer, instead of in an encyclopedia.
YesYConverted to prose and merged with Resistance.CrazyChemGuy (talk) 19:02, 30 April 2008 (UTC)
  • The 'resistance' section is very short, and could probably be combined with another section. It seems out of place in the lineup of sections here. On it's own, it doesn't comply with WP:MEDMOS.
YesYMerged with Contraindications.CrazyChemGuy (talk) 19:02, 30 April 2008 (UTC)
  • Likewise, 'polymorphism' is also very short, and should probably be combined with another section as well. Perhaps add it to a section on 'chemical and physical properties', in a discussion on the structure.
YesYMerged, along with Synthesis, into section on Chemistry. CrazyChemGuy (talk) 23:12, 2 May 2008 (UTC)
  • There's no information on pharmacokinetics (absorption, distribution, metabolism, and excretion) in the article.
YesYA section on pharmacokinetics has been added.CrazyChemGuy (talk) 19:02, 30 April 2008 (UTC)

These are the biggest issues with the article the way I see them now. I will put the article on hold for one week and review it again after that. Dr. Cash (talk) 23:46, 27 April 2008 (UTC)

There are more comments which should be addressed in the current peer review for the article (although for future reference peer review should not be conducted at the same time as a GA review). Dr. Cash (talk) 23:49, 27 April 2008 (UTC)
Dosage strengths removed as per above comments and WP:MEDMOS (vary by country, individual products and age). See changes. Patient product literature, the references given and most importantly the prescription instructions of ones own doctor should be followed... In teh case of thromboprophylaxis, some advocate 75mg, others 150mg and that's just in UK (little evidence for either of these doses - just historical usuage) and different values used in US I believe - sufficent to point out much lower strengths and once daily rather than multiple dosing when used as an analgesic. David Ruben Talk 11:43, 28 April 2008 (UTC)
  • Oppose. Out of the first four references I checked, three were false in the sense that they stated exactly the opposite of what was written in the article. Serious (and long) work is needed to re-check all the references. I will fail the article unless somebody thinks it is unfair. Paul Gene (talk) 10:34, 29 April 2008 (UTC)
I won't oppose your opposition, but I looked at those references and I don't think the situation is as simple as you put it. It illustrates the larger problem of writing about recent medical studies, and that is that there are no definite conclusions in many cases and one can always find a study with the opposite result. For example, let's look at the prostate cancer issue you addressed in this edit. The two references provided are for individual studies that had negative results, but they acknowledge that there is an existing hypothesis and do not claim to have disproven it definitely but end with weaker statements such as "These data suggest that aspirin use may not be associated with reduced risk of prostate cancer" and "These findings do not support a protective role of regular aspirin use on prostate cancer risk". This is because it's hard to be certain from just one study; if you look for example at PMID 15998950 , that one ends with "These results support the hypothesis that long duration regular NSAID use is associated with modestly reduced risk of prostate cancer." So what is the truth? I have no idea, and I'm not a specialist in prostate cancer or aspirin, like most Wikipedia editors here, I imagine. The only thing I can say is that some studies support the hypothesis and some don't. I can also see from reading the abstracts that there are different definitions of regular aspirin use. One of the negative studies defined it as once per week for six months, while the positive study defined it as 30 per month for 5 years. That already is an obvious difference that might explain the different results.
The real question is, what should the Wikipedia article say? I think the original text was reasonably cautious, as it said "The drug may be effective..." (that is, it may or may not...). The problem is that it only cited specific negative studies. Ideally it should cite a review or meta analysis that can attempt to provide a bigger and more balanced picture. If no such reference exist, at least it should say "some studies support this hypothesis[ref] and some don't[ref]. Another option is to try to avoid reporting the bleeding edge of medical research on Wikipedia, as it is very hard to do it in a balanced way. Let's wait until the research makes it into the textbooks rather than citing very recent specific studies. I suspect this will not be the most popular option because some people will be afraid of looking outdated, but for an encyclopedia this can be better than looking like the evening news shows, which one day report "X cures cancer!" and the next day report "X causes cancer!", which only results in confusion to the audience. --Itub (talk) 11:27, 29 April 2008 (UTC)
No, you misunderstood. Of course you can cite the most recent research in WP! All I want is this — if it is written "aspirin prevents cancer", the references given should support this. So if references say "mostly likely not" the article should say "most likely not" — not "likely yes". Since this problem keeps occurring in this article, (I saw it before in the chemistry part) I conclude that a serious work is needed to check all the references, and it is premature to promote it to GA. Paul Gene (talk) 18:09, 29 April 2008 (UTC)
I don't think it's time to fail the article just yet. When the article was first placed on hold, a week was given for improvements to be made. While I do agree with you that the issue of the citations needs to be addressed, failing the article will only take away motivation for the article to be improved. Personally, with my current real life workload, I should get plenty of time to work on the article later in the week. I may not be able to fix everything that has been suggested here, but even then, the article would still be better than if it was failed immediately. I would strongly suggest keeping the article on hold to see if these issues can't be fixed. CrazyChemGuy (talk) 20:58, 29 April 2008 (UTC)
The article certainly won't be failed right now; part of the process of GA review is a general improvement phase, which includes addressing issues are they pertain to the Good Article criteria. Some articles pass easily; others take more time; hence the reason for the on hold step. It would be more helpful, though, if Paul would be more specific in the concerns regarding citations. Simply saying, "Out of the first four references I checked, three were false..." isn't really all that helpful. Which ones were "false"? Where do you see the problems. Let's try and help each other out here rather than being vague and throwing out "oppose" votes (it's not a vote). Dr. Cash (talk) 21:09, 29 April 2008 (UTC)
Read the discussion and edit history. My point is that article is very far from GA. There are major not merely cosmetic issues. Paul Gene (talk) 22:43, 29 April 2008 (UTC)
On a side note, I've added a section about pharmacokinetics. The prose could probably use some work, as I admit I'm not the best at that, and it sounds rather technical, but I did try to ensure that my sources were quite reliable - in this case, they are all from well known medical journals, such as JAMA. I think this should improve the article a lot, once the section gets smoothed out (along with the prose/copyediting needs of the rest of the article); if anyone has any suggestions about how to improve this section I'd love to hear them. CrazyChemGuy (talk) 23:50, 29 April 2008 (UTC)

I still have some issues, mainly with some of the references, and am having a hard time passing it as is.

  • In the lead: "Low doses of aspirin may also be given immediately after a heart attack; these doses may inhibit the synthesis of prothrombin and therefore produce a second and different anticoagulant effect,[1] although this is not well understood." Why is the citation on the statement right after the comma, not after the sentence. If it's not well understood, says who? If there are disputes in the literature, this should be pointed out. But I wouldn't focus on something somewhat controversial in the lead; the lead should summarize the article. Focus on experimental treatments later in the article.
  • The last two paragraphs of the history section have completely uncited material.
  • A copyedit should still be done. I can see several instances where there should be commas. Others were there shouldn't be. Others were phrasing is awkward.
  • Some of the references in the 'therapeutic uses' section just aren't used very well. For example, in this sentence: "Aspirin is one of the most frequently used drugs in the treatment of mild to moderate pain, including that of migraines,[7] and fever." why is the citation on the migraines, and why is there a comma after migraines. It should be relatively trivial to find a damn pharmacology book that backs up the whole sentence, and put a citation after the whole thing, instead of in the middle. It seems like editors here are trying to use a wikipedia reference to give more weight to someone's paper, instead of just citing this from a book -- this is really basic info here.
  • The overciting of other material can be seen in the 'experimental uses' section, specifically in the sentence on reducing the risk of various cancers. Five citations after the gastrointestinal bleeding part, two after "lung", two at the end of the whole sentence!! I think we need to really look at what citations are really necessary here, and which ones are merely filler. Citations that aren't really necessary can be removed.

I'd still like to see this get to GA, but I still don't think we're quite there yet. It's already been quite awhile on hold, so try and finish this up by saturday, or I'll really have no choice but to fail it. Dr. Cash (talk)

I'm not quite sure that the material in the 'experimental uses' section is overcited. I checked each citation, and one of them was not properly placed, and I moved it, but other than that it did indeed seem that they all supported the material the claimed too. Given that the correlation between aspirin use and various types of cancer isn't simply something that is widely accepted, I think it's okay to have that many citations there - I think claims such as a correlation between aspirin and colon cancer needs several studies to be cited and all in agreement. I'm not quite sure why you feel it is a problem for this information to be "over" cited. After editing the article some more, I can't find much else in the article to improve, save for perhaps some copyediting, though I'm sure much of this is just because I've been staring at this same text for as long as I have. I think it's at the point now where it can pass as a GA, especially after I give it a good copyedit here, but the real test of this will be in the eyes of a fresh, unbiased editor, so... I suppose it's time to see what you think. CrazyChemGuy (talk) 15:30, 17 May 2008 (UTC)

Some points

I will try to do a formal GA review later, but quickly some points:

  • Why is the chemistry section at the bottom? Wouldn't it make more sense to progress from chemistry to pharmacology to clinical uses to contraindications/adverse events?
  • The external links seem to generally be duplicating the content of the history and pharmacology sections.
  • Ref 28 looks borky. Needs proper formatting (AHA).
  • Some other references are bare URLs.
  • The treatment of toxicity is still a bit vague. What is actually done is the use of bicarbonate solution to acidify the urine and aid in the excretion of salicylates. This needs a good reference.

I was a bit dismayed that we allowed a citation "aspirin may increase pancreatic cancer risk" based on a single study. People read Wikipedia and do get worried about such claims. In this case I easily found a later study that disproved the association, but we really ought to be careful. JFW | T@lk 07:27, 7 May 2008 (UTC)

I think I agree with Paul Gene above that this article still needs some work before it will reach GA. JFW | T@lk 07:30, 7 May 2008 (UTC)
Like I said above, citing specific single studies is dangerous, and there are many such citations in this article. For every study, you can always find another study the opposite result. ;-) Therefore, I suggest we should try to cite only secondary literature that reviews multiple studies and puts them into perspective. --Itub (talk) 09:30, 7 May 2008 (UTC)
There is nothing wrong with citing particular studies, especially if they have made some waves, but my point here was that the "aspirin causes cancer" link had been disproven by subsequent research. Omitting the meta-analysis was IMHO irresponsible.
Which other "single studies" are you referring to? JFW | T@lk 20:50, 7 May 2008 (UTC)
For example, the sentence "Aspirin did not reduce cataract formation in diabetic patients.[11]" This is citing one study from 1992 which in fact reached this conclusion. But what about the earlier studies that reached the opposite conclusion? How about mentioning why someone might think that aspirin might reduce cataract formation in the first place? When I see a statement this on Wikipedia, based on one, seemingly cherry-picked specific study, I can think of three things: 1) the user who added it is an expert who knows that this is the scientific consensus and that the cited study is considered the "gold standard" in the field; 2) the user stumbled on this study for whatever reason, thought it was interesting, and cited it, without looking at the broader context (probably without even reading it); or 3) the user who added it has an agenda and is purposefully adding only one side of the story. I would like to hope that the right explanation is 1), but I'm afraid that most of the time it's not, and in fact Wikipedia content policies on neutrality and verifiability are based on the assumption that it's not.
Let me give you an example of how I think such a statement should be presented. These are the first few sentences from the introduction of a 2001 paper, PMID 11231774: "A possible role for aspirin in reducing risks of cataract was first suggested in studies of patients with arthritis or diabetes mellitus[1-2] and in a study of patients undergoing cataract surgery.[3] Most subsequent observational epidemiologic studies, however, have generally shown no association between self-selected aspirin use and cataract.[4-14] Results from 2 of 3 randomized trials that included an evaluation of the aspirin-cataract hypothesis also indicate no apparent benefit of aspirin in reducing risks of cataract...". OK, we don't really need to give 14+ references for this minor part of this Wikipedia article, but we could at least write the text in a similar manner and attribute it to the 2001 paper. This would also have the advantage of being 9 years more recent and based on more subsequent studies. Note that the citation would be not so much to point to the results of the 2001 study, but to the mini-review contained in the introduction of the paper (so that we don't need to cite the 14+ references ourselves). Or ideally, if there is a review we can cite that would be better.
I haven't looked at the other references in the Wikipedia article in detail, but I suspect that a similar problem will occur with some of the references in the "Experimental uses" and "Adverse effects" sections. --Itub (talk) 08:50, 8 May 2008 (UTC)

GA status update

I've checked the article and cleaned up a few minor grammatical issues. I've also checked all the references in the 'experimental uses' section, and they all appear to support what they are citing; though I rephrased the part about pancreatic cancer, since both citations came to different conclusions. Other than these issues, I don't see any other major issues with the GA criteria, and I think it can be passed. Since we've already pretty much exhausted the limit of on hold status already, a decision needs to be made. Unless there are other major objections by either Paul Gene or JFW, I will pass this article as a Good Article in 48 hours. Dr. Cash (talk) 16:28, 28 May 2008 (UTC)

Seeing no evidence of further issues from others, I have passed this article as a Good article. Congratulations! Dr. Cash (talk) 14:26, 30 May 2008 (UTC)

Reversion of edit by Paul Gene

I recently made this edit: [7]. I don't think that the source in question is unreliable or that the content needs to be removed- as there is plenty of information out there to support that statement, I think the best course of action if one feels the source given was not reliable would be to find another source and add it. The source may not be scholarly, perhaps, but the opinion that old aspirin smells like vinegar was given by a qualified person with a PhD in the relevant area - their qualifications were listed on the page listed.CrazyChemGuy (talk) 00:12, 30 April 2008 (UTC)

The sentence being discussed is this: Formulations containing high concentrations of aspirin often smell like vinegar.[4] It has the following problems. First, the sentence implies that "high concentrations" of aspirin are somehow special and so lower concentrations would not smell like vinegar, which is strange. Second, references to bulletin boards are generally not considered reliable on WP (see WP:RS), anybody can say that he is a prof and PhD. Third, if you read the bulletin board text, there is nothing about "high concentration formulations", it is about old solid aspirin smelling like vinegar, so it duplicates the next sentence: "aspirin can decompose in moist conditions, yielding salicylic acid and acetic acid.[5]" Perhaps we just should leave this last sentence, which also has a proper quotation. Paul Gene (talk) 01:03, 30 April 2008 (UTC)
I would be okay to leave only the last part of that sentence now. I do know that the decomposition of aspirin is autocatylitic and also results in a vinegar odor (I mean, seriously, acetic acid), so I will look for a reliable source- perhaps I'll try the local library for a print source, I haven't found much about it being autocatylitic on google - because I do think that stuff needs to go back in eventually, as it is relevant. I'll look for things on a few of the other troubled citations too, while I'm there tomorrow anyway. CrazyChemGuy (talk) 02:29, 30 April 2008 (UTC)
On a related note, I am removing the following statement: "Another study, however, has reported that the incidence of these side effects, when compared to those of some other forms of aspirin, may be reduced by taking aspirin an enteric coated form. [41] 104 participants were given a 14 day trial on the different types of aspirin being tested. After day 14, the dosage was lowered and reductions in gastric effects were seen in those with the enteric coated aspirin."
This statement is completely incorrect. For 14 days the patients were given 75 mg of EC aspirin. And then either continued with the same dose or with increased dose (150 mg) of EC aspirin or with 162 mg of microencapsulated aspirin. Gastric side effects were not measured, so this reference is irrelevant to the topic of side effects. By the way the lit. review part of this paper states "Whilst both enteric coating and buffering agents may theoretically reduce irritation of gastric mucosa, blood levels are just as high as with conventional aspirin and recent work has shown similar rates of bleeding with these preparations" that is the reverse of what it is purported to state. Paul Gene (talk) 01:36, 30 April 2008 (UTC)

False references

A relevant discussion on false references we had with CrazyChemGuy on my talk page:


Hi, you have removed several references from Aspirin as being false or not relevant in the way they are cited. I do wonder if on some of them, such as [1], the reference does in fact support the material - even if it is not mentioned in the abstract, the full text of the article may still have information that supports the sentence, could it not? Personally, I have not read the article in question, nor have I read several other of the articles you removed as citations, but do you think maybe one should be a little careful when removing such sourced information? I realize some people do do this, but I doubt that many editors would intentionally introduce sources that are not relevant to the material. I'm not saying you've done anything wrong; I'm just curious if you have double checked all of these references. CrazyChemGuy (talk) 00:05, 30 April 2008 (UTC)
I would have checked a full text if it were a well and competently written article. It is not. I checked, however, the full text for the reference you mentioned. And no, the full text does not support that nonsense. 103 out of 160 people had GI symptoms, not 160. In any case this study cannot be used to establish the frequency of GI symptoms that can be specifically attributed to aspirin. To do that it had to be randomized and, ideally, blinded. Second, using citations, which are at best tangential to the material they purport to prove, is a common phenomenon on WP. I would not guess what its causes are. To make everybody's life easier, the WP guidelines generally recommend that in the onus of finding a proof is on the person who inserts information into the article. Cheers, Paul Gene (talk) 00:24, 30 April 2008 (UTC) Paul Gene (talk) 01:41, 30 April 2008 (UTC)

Small Text

Pharmacokinetics

The pH of the small intestine is alkaline, (very), and not acidic. Aspirin is very soluble in the duodenum. GrahamColmTalk 11:29, 27 May 2008 (UTC)

You're correct. It seems I screwed that up when I wrote the secton - an IP changed acidity to pH, which is what I meant to type, but I reverted the edit without paying much attention [8]. Thanks for pointing this error out - I've edited the pharmacokinetics section to fix this error. CrazyChemGuy (talk) 16:59, 27 May 2008 (UTC)
  1. ^ Stone, E (1763). "An Account of the Success of the Bark of the Willow in the Cure of Agues". Philosophical Transactions 53: 195–200. 
  2. ^ a
  3. ^ b>
  4. ^ "http://www.newton.dep.anl.gov/askasci/chem00/chem00314.htm". Retrieved 04-29-08.  Check date values in: |accessdate= (help)
  5. ^ Carstensen, J.T.; F Attarchi and XP Hou (July 1985). "Decomposition of aspirin in the solid state in the presence of limited amounts of moisture.". Journal of Pharmaceutical Sciences 77 (4): 318–321. Retrieved 2008-04-28.