Aminophenazone: Difference between revisions

{{Short description|Non-narcotic analgesic drug}}

{{cs1 config|name-list-style=vanc}}

{{more citations needed|date=March 2020}}

| verifiedrevid = 443384468

| INN = aminophenazone

| IUPAC_name = 4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one

| image = Aminophenazone-2d-skeletal.png

| width = 180px

| image2 = Aminophenazone-3D-balls.png

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|international|aminophenazone}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration =

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism = N-demethylation<ref name="Caubet2007">{{cite journal | vauthors = Caubet MS, Laplante A, Caillé J, Brazier JL | title = [¹³C]aminopyrine and [¹³C]caffeine breath test: influence of gender, cigarette smoking and oral contraceptives intake | journal = Isotopes in Environmental and Health Studies | volume = 38 | issue = 2 | pages = 71–7 | date = June 2002 | pmid = 12219983 | doi = 10.1080/10256010208033314 | bibcode = 2002IEHS...38...71C | s2cid = 22002940 }}</ref>

| elimination_half-life =

| excretion =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 58-15-1

| ATC_prefix = N02

| ATC_suffix = BB03

| PubChem = 6009

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01424

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00556

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 160246

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 288470

<!--Chemical data-->

| C=13 | H=17

| N=3 | O=1

'''Aminophenazone''' (or '''aminopyrine, amidopyrine, Pyramidon''') is a non-narcotic [[analgesic]] substance. It is a [[pyrazolone]] and a derivative of [[phenazone]], which also has anti-inflammatory and [[antipyretic]] properties. While inexpensive and effective, especially in the treatment of [[rheumatism]], the drug carries a serious risk of severe and sometimes fatal side-effects, including [[agranulocytosis]].{{cn|date=April 2023}} While its production and use have been banned in many countries, including France, Thailand, India and Japan, it is still sometimes used in the developing world.{{Cn|date=April 2023}}

A breath test with [[Carbon-13|¹³C]]-labeled aminopyrine has been used as a non-invasive measure of [[cytochrome]] P-450 metabolic activity in liver-function tests.<ref name="Caubet2007" /> It is also used in measuring the total body water in the human body system.<ref>{{cite web

| date= 2005-03-26

| url= https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6009&loc=ec_rcs

| title= Aminophenazone — Compound Summary

| work= PubChem

| publisher= The National Library of Medicine

| access-date= June 12, 2008

== History ==

Aminophenazone was first synthesized by [[Friedrich Stolz]] and [[Ludwig Knorr]] in the late nineteenth century, and sold as an anti-fever medicine known as Pyramidon by [[Hoechst AG]] from 1897 until its eventual replacement{{when|date=March 2020}} by the safer [[propyphenazone]] molecule.

== Symptoms ==

Symptoms of exposure to this compound include:<ref name=":0">{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/aminopyrine#section=Health-Hazard|title=aminophenazone|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2017-11-09}}</ref>

* allergic reactions

* strong [[Spasmolytics|spasmolytic]] effect on smooth muscle of peripheral blood vessels

* irritability

* [[Cerebral palsy|palsy]]

* copious sweating

* dilated pupils

* sharp drop then rise in body temperature

* [[dysuria]]

* [[dyspnea]]

* [[anxiety]]

* [[rectal tenesmus]]

* urinary frequency

* intermittent fever

* fatty infiltration of the liver

* heart muscle degeneration

* death due to circulatory failure following [[cardiovascular collapse]]

[[Agranulocytosis]] often occurs. Ingestion may cause central nervous system stimulation, vomiting, convulsions, [[cyanosis]], [[tinnitus]], [[leukopenia]], kidney damage and coma. Ingestion may also lead to nausea, mental disturbances, [[methemoglobinemia]], chocolate-colored blood, dizziness, epigastric pain, difficulty in hearing, thready pulse and liver damage.

Other symptoms reported via ingestion include [[hemolytic anemia]], [[porphyria]] and severe gastrointestinal bleeding. [[Bone marrow depression]] also occurs. Rare eye effects include [[Myopia|acute transient myopia]].

Chronic symptoms include:

* [[Anorexia nervosa|anorexia]]

* [[edema]]

* [[oliguria]]

* [[urticaria]]

* hypersensitivity

* [[aplastic anemia]]

* sore throat

* fever

* pharyngeal membrane

* jaundice enlargement of the liver and spleen

* [[exfoliative dermatitis]]

* gastric or duodenal erosion with perforation or bleeding

* adrenal [[necrosis]]

* [[thrombocytopenic purpura]]

* acute [[leukemia]]

When heated to decomposition this compound emits toxic fumes of [[nitrogen oxide]]s.

== Metabolism ==

Amidopyrine is metabolized by demethylation and acetylation. Amidopirina metabolites are 4-aminoantipyrine, metilaminoantipirin, rubazonovaya and metilrubazonovaya acid. These acids have a reddish color. At high amidopirine doses, urine can have a reddish brown coloration, due to the presence in the urine of these acid markers.<ref>{{Cite web|url=http://soundlike.ru/english/articles.php?id=4149|title=Amidopirina|last=Vyzanie|website=soundlike.ru|access-date=2017-11-09|archive-date=2022-02-01|archive-url=https://web.archive.org/web/20220201072441/http://soundlike.ru/english/articles.php?id=4149|url-status=dead}}</ref>

{{reflist}}

{{Analgesics}}

[[Category:Antipyretics]]

[[Category:Nonsteroidal anti-inflammatory drugs]]