Aminophenazone

Aminophenazone
INN: aminophenazone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N02BB03 (WHO) ;
Pharmacokinetic data
Metabolism	N-demethylation
Identifiers
	IUPAC name 4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one;
CAS Number	58-15-1 ;
PubChem CID	6009;
DrugBank	DB01424 ;
ChemSpider	5787 ;
UNII	01704YP3MO;
KEGG	D00556 ;
ChEBI	CHEBI:160246 ;
ChEMBL	ChEMBL288470 ;
CompTox Dashboard (EPA)	DTXSID7020504 ;
ECHA InfoCard	100.000.332
Chemical and physical data
Formula	C13H17N3O
Molar mass	231.299 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2\C(=C(/N(N2c1ccccc1)C)C)N(C)C;
	InChI InChI=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 ; Key:RMMXTBMQSGEXHJ-UHFFFAOYSA-N ;
	(verify)

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 and Japan, 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.^[1] It is also used in measuring the total body water in the human body system.^[2]

^ ^a ^b Caubet MS, Laplante A, Caillé J, Brazier JL (June 2002). "[¹³C]aminopyrine and [¹³C]caffeine breath test: influence of gender, cigarette smoking and oral contraceptives intake". Isotopes in Environmental and Health Studies. 38 (2): 71–7. Bibcode:2002IEHS...38...71C. doi:10.1080/10256010208033314. PMID 12219983. S2CID 22002940.
^ "Aminophenazone — Compound Summary". PubChem. The National Library of Medicine. 2005-03-26. Retrieved June 12, 2008.

[Caubet2007-1] Caubet MS, Laplante A, Caillé J, Brazier JL (June 2002). "[¹³C]aminopyrine and [¹³C]caffeine breath test: influence of gender, cigarette smoking and oral contraceptives intake". Isotopes in Environmental and Health Studies. 38 (2): 71–7. Bibcode:2002IEHS...38...71C. doi:10.1080/10256010208033314. PMID 12219983. S2CID 22002940.

[2] "Aminophenazone — Compound Summary". PubChem. The National Library of Medicine. 2005-03-26. Retrieved June 12, 2008.

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