Aminophenazone
{{Short description|Non-narcotic analgesic drug}}
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{{more citations needed|date=March 2020}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443384468
| INN = aminophenazone
| IUPAC_name = 4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one
| image = Aminophenazone-2d-skeletal.png
| image_class = skin-invert-image
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| image2 = Aminophenazone-3D-balls.png
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| Drugs.com = {{drugs.com|international|aminophenazone}}
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| 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
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5787
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 01704YP3MO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00556
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 160246
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 288470
| C=13 | H=17
| N=3 | O=1
| smiles = O=C2\C(=C(/N(N2c1ccccc1)C)C)N(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3
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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 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver-function tests. It is also used in measuring the total body water in the human body system.{{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:{{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}}
- allergic reactions
- strong spasmolytic effect on smooth muscle of peripheral blood vessels
- irritability
- 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 acute transient myopia.
Chronic symptoms include:
- 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 oxides.
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.{{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}}
In popular culture
Hospital Universitario Ramón y Cajal in Madrid, Spain was built as a center for specialized surgery, a panacea for the ills of the health system in Madrid.