Structure via PubChem · Public domain (PubChem)
aminophenazone
Sign in to saveAlso known as 1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone, 4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, 4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one, Aminophenazon, 4-Dimethylaminophenazone, Dipyrine, Dimethylaminophenyldimethylpyrazolone, 4-Dimethylaminoantipyrine
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. While its production and use have been banned in many countries, including France, Thailand, India, Japan and USA, it is still sometimes used in the developing world.
Chemical data
- Formula
- C13H17N3O
- Molecular weight
- 231.29 g/mol
- IUPAC name
- 4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one
- SMILES
- CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)C
- InChIKey
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 26.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,155 papers- [Intravenous aminophenazone].Medizinische Klinik · 1953
- [Has aminophenazone a carcinogenic effect?].MMW, Munchener medizinische Wochenschrift · 1976
- [Combined aminophenazone therapy].Der Nervenarzt · 1957
- Allopurinol influences aminophenazone elimination.Clinical pharmacokinetics · 1990
- Oral antipyretic therapy.Scandinavian journal of rheumatology · 1976
via PubMed
Wikidata facts
- Mass
- 231.137162
Show 6 more facts
- melting point
- 107
- chemical formula
- C₁₃H₁₇N₃O
- Commons category
- Aminophenazone
- canonical SMILES
- CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)C
- World Health Organisation international non-proprietary name
- aminophenazone
- defined daily dose
- 0.5
Sources (3)
via Wikidata · CC0
~4 min read
Article
6 sectionsContents
- History
- Symptoms
- Metabolism
- Drug Interactions
- In popular culture
- References
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. While its production and use have been banned in many countries, including France, Thailand, India, Japan and USA, it is still sometimes used in the developing world.
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.