Amoxicillin: Difference between revisions
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==Medical uses== |
==Medical uses== |
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Amoxicillin is used in the treatment of a number of infections including: [[acute otitis media]], [[streptococcal pharyngitis]], [[pneumonia]], [[cellulitis|skin infections]], [[urinary tract infection]]s, ''[[salmonella]]'', [[lyme disease]], and chlamydia infections.<ref name=AHFS>{{cite web|title=Amoxicillin|url=http://www.drugs.com/monograph/amoxicillin.html|work=The American Society of Health-System Pharmacists|accessdate=3 April 2011}}</ref> It is also used to prevent [[bacterial endocarditis]] in high risk people who are having dental work done, to prevent ''strep pneumococus'' infections in those without a [[spleen]], and for both the prevention and the treatment of [[anthrax]].<ref name=AHFS/> |
Amoxicillin is used in the treatment of a number of infections including: [[acute otitis media]], [[streptococcal pharyngitis]], [[pneumonia]], [[cellulitis|skin infections]], [[urinary tract infection]]s, ''[[salmonella]]'', [[lyme disease]], and chlamydia infections.<ref name=AHFS>{{cite web|title=Amoxicillin|url=http://www.drugs.com/monograph/amoxicillin.html|work=The American Society of Health-System Pharmacists|accessdate=3 April 2011}}</ref> It is also used to prevent [[bacterial endocarditis]] in high risk people who are having dental work done, to prevent ''strep pneumococus'' infections in those without a [[spleen]], and for both the prevention and the treatment of [[anthrax]].<ref name=AHFS/> The UK however does not recommend its use for infectious endocarditis prophylaxis.<ref>{{cite web|title=CG64 Prophylaxis against infective endocarditis: Full guidance|url=http://www.nice.org.uk/nicemedia/live/11938/40039/40039.pdf|work=NICE|accessdate=8 June 2011}}</ref> These recommendations have not appeared to have changed the rates of infection.<ref>{{cite journal|last=Thornhill|first=MH|coauthors=Dayer, MJ, Forde, JM, Corey, GR, Chu, VH, Couper, DJ, Lockhart, PB|title=Impact of the NICE guideline recommending cessation of antibiotic prophylaxis for prevention of infective endocarditis: before and after study|journal=BMJ (Clinical research ed.)|date=2011 May 3|volume=342|pages=d2392|pmid=21540258|doi=10.1136/bmj.d2392|pmc=3086390}}</ref> |
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Amoxicillin is a correct first-choice drug to be used in treating bacterial [[sinusitis]] but it is often prescribed incorrectly to treat viral sinusitis.<ref name="AAAAIfive">{{Citation |author1 = American Academy of Allergy, Asthma, and Immunology |author1-link = American Academy of Allergy, Asthma, and Immunology |date = |title = Five Things Physicians and Patients Should Question |publisher = [[American Academy of Allergy, Asthma, and Immunology]] |work = Choosing Wisely: an initiative of the [[ABIM Foundation]] |page = |url = http://choosingwisely.org/wp-content/uploads/2012/04/5things_12_factsheet_AAAAI.pdf |accessdate = August 14 2012}}</ref><ref name="antibioticssinusitis">{{cite doi|10.1002/14651858.CD000243.pub2}}</ref> Amoxicillin is occasionally used for the treatment of skin infections, such as [[acne vulgaris]].<ref>{{cite web | title = Adolescent Acne: Management | url = http://www.medscape.com/viewarticle/430534_5}}</ref> Amoxicillin is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, like [[doxycycline]] and [[minocycline]].<ref>{{cite web|url=http://scienceofacne.com/amoxicillin/|title=Amoxicillin and Acne Vulgaris |publisher=scienceofacne.com |date=2012-09-05 |accessdate=2012-08-17}}</ref> |
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== Adverse effects == |
== Adverse effects == |
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Revision as of 16:46, 27 August 2012
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| Clinical data | |
|---|---|
| Trade names | Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a685001 |
| Pregnancy category |
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| Routes of administration | Oral, intravenous |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 95% oral |
| Metabolism | less than 30% biotransformed in liver |
| Elimination half-life | 61.3 minutes |
| Excretion | renal |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.043.625 |
| Chemical and physical data | |
| Formula | C16H19N3O5S |
| Molar mass | 365.4 g/mol g·mol−1 |
| 3D model (JSmol) | |
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| (verify) | |
Amoxicillin (INN), formerly amoxycillin (BAN), and abbreviated amox, is a moderate-spectrum, bacteriolytic, β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. Amoxicillin is one of the most common antibiotics prescribed for children.
Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to a broad spectrum of β-lactam antibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a β-lactamase inhibitor. This increases effectiveness by reducing its susceptibility to β-lactamase resistance.
Medical uses
Amoxicillin is used in the treatment of a number of infections including: acute otitis media, streptococcal pharyngitis, pneumonia, skin infections, urinary tract infections, salmonella, lyme disease, and chlamydia infections.[1] It is also used to prevent bacterial endocarditis in high risk people who are having dental work done, to prevent strep pneumococus infections in those without a spleen, and for both the prevention and the treatment of anthrax.[1] The UK however does not recommend its use for infectious endocarditis prophylaxis.[2] These recommendations have not appeared to have changed the rates of infection.[3]
Amoxicillin is a correct first-choice drug to be used in treating bacterial sinusitis but it is often prescribed incorrectly to treat viral sinusitis.[4][5] Amoxicillin is occasionally used for the treatment of skin infections, such as acne vulgaris.[6] Amoxicillin is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, like doxycycline and minocycline.[7]
Adverse effects
Side-effects are as those for other beta-lactam antibiotics. Side-effects include nausea, vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhoea) may also occur. Rarer side-effects include mental changes, lightheadedness, insomnia, confusion, anxiety, sensitivity to lights and sounds, and unclear thinking. Immediate medical care is required upon the first signs of these side-effects.
The onset of an allergic reaction to amoxicillin can be very sudden and intense - emergency medical attention must be sought as quickly as possible. The initial onset of such a reaction often starts with a change in mental state, skin rash with intense itching (often beginning in fingertips and around groin area and rapidly spreading), and sensations of fever, nausea, and vomiting. Any other symptoms that seem even remotely suspicious must be taken very seriously. However, more mild allergy symptoms, such as a rash, can occur at any time during treatment, even up to a week after treatment has ceased. For some people who are allergic to amoxicillin the side-effects can be deadly.
Use of the amoxicillin/clavulanic acid combination for more than one week has caused mild hepatitis in some patients. Young children having ingested acute overdoses of amoxicillin manifested lethargy, vomiting and renal dysfunction.[8][9]
Nonallergic amoxicillin rash
Somewhere between 3% and 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously), often itchy rash, which is sometimes referred to as the "amoxicillin rash." The rash can also occur in adults.
The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash"[10]). It starts on the trunk and can spread from there. This rash is unlikely to be a true allergic reaction, and is not a contraindication for future amoxicillin usage, nor should the current regimen necessarily be stopped. However, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, and therefore a healthcare professional is often required to distinguish between the two.[11]
A nonallergic amoxicillin rash may also be an indicator of infectious mononucleosis: Some studies indicate approximately 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.[12]
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Nonallergic amoxicillin rash 8 days after first dose, 24 hours after rash began. Diagnosed by a pediatric resident at local university hospital. -
Eight hours after first photo, individual spots have grown and begun to merge. -
Twenty-three hours after first photo, the color appears to be fading, and much of rash has spread to confluence.
Interaction
Amoxicillin may interact with the following groups of drugs:
- Anticoagulants (e.g. warfarin, pradaxa)[13]
- Allopurinol (gout treatment)
- Birth control pills[citation needed]
- Certain antibiotics
- Cancer treatment (methotrexate)
- Uricosuric drugs
- Typhoid vaccine
Mechanism of action
This drug acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria.
It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group).
Spectrum of Bacterial Susceptibility and Resistance
Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter and Moraxella species are generally susceptible to amoxicillin, while Citrobacter, Klebsiella and Pseudomonas aeruginosa are resistant to amoxicillin.[14] Some E. Coli and Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.
Formulations
Modes of delivery
Pharmaceutical manufacturers make amoxicillin in trihydrate form available as capsules, chewable and dispersible tablets plus syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration (although the IV formulation is not available in the United States[15]).
Amoxicillin is most commonly taken orally. The liquid forms are helpful where the patient might find it difficult to take tablets or capsules.
Research with mice (published in 2010) indicates successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.[16]
Proprietary preparations
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Amoxicillin is one of the semisynthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names, including:
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References
- ^ a b "Amoxicillin". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
- ^ "CG64 Prophylaxis against infective endocarditis: Full guidance" (PDF). NICE. Retrieved 8 June 2011.
- ^ Thornhill, MH (2011 May 3). "Impact of the NICE guideline recommending cessation of antibiotic prophylaxis for prevention of infective endocarditis: before and after study". BMJ (Clinical research ed.). 342: d2392. doi:10.1136/bmj.d2392. PMC 3086390. PMID 21540258.
{{cite journal}}: Check date values in:|date=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ American Academy of Allergy, Asthma, and Immunology, "Five Things Physicians and Patients Should Question" (PDF), Choosing Wisely: an initiative of the ABIM Foundation, American Academy of Allergy, Asthma, and Immunology, retrieved August 14 2012
{{citation}}: Check date values in:|accessdate=(help)CS1 maint: multiple names: authors list (link) - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/14651858.CD000243.pub2, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1002/14651858.CD000243.pub2instead. - ^ "Adolescent Acne: Management".
- ^ "Amoxicillin and Acne Vulgaris". scienceofacne.com. 2012-09-05. Retrieved 2012-08-17.
- ^ Cundiff J, Joe S. Amoxicillin-clavulanic acid-induced hepatitis. Amer. J. Otolaryngol. 28: 28-30, 2007.
- ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 81-83.
- ^ "Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes". Cat.inist.fr. Retrieved 2010-11-13.
- ^ (Pichichero, 2005; Schmitt 2005)
- ^ Kagan, B (1977). "Ampicillin rash". Western Journal of Medicine. 126 (4): 333–335. PMC 1237570. PMID 855325.
- ^ British National Formulary 57 March 2009
- ^ "Amoxicillin spectrum of bacterial susceptibility and Resistance" (PDF). Retrieved 8 April 2012.
- ^ www.UpToDate.com
- ^ Amoxicillin bearing microparticles: potential in treatment of Listeria monocytogenes infection in Swiss albino mice, Bioscience reports immediate publication, 2010-08-05, manuscript BSR 20100027
Ezymox 500mg
Further reading
- Neal, M. J. (2002). Medical pharmacology at a glance (4th ed.). Oxford: Blackwell Science. ISBN 0-632-05244-9.
- Pichichero ME (2005). "A review of evidence supporting the American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients". Pediatrics. 115 (4): 1048–57. doi:10.1542/peds.2004-1276. PMID 15805383.
{{cite journal}}: Unknown parameter|month=ignored (help) - Schmitt, Barton D. (2005). Your child's health: the parents' one-stop reference guide to symptoms, emergencies, common illnesses, behavior problems, healthy development (2nd ed.). New York: Bantam Books. ISBN 0-553-38369-8.
- British National Formulary 45 March 2003
External links
- University of Michigan Mott's Children's Hospital article about "amoxicillin rash."[dead link] (Very similar to Schmitt 2005 content)[dead link]
- U.S. National Library of Medicine: Drug Information Portal - Amoxicillin