Phenazone

Phenazone
Clinical data
Other names	analgesine, antipyrine
ATC code	N02BB01 (WHO) S02DA03 (WHO);
Pharmacokinetic data
Elimination half-life	12 hours
Identifiers
	IUPAC name 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one;
CAS Number	60-80-0 ;
PubChem CID	2206;
DrugBank	DB01435 ;
ChemSpider	2121 ;
UNII	T3CHA1B51H;
KEGG	D01776 ;
ChEBI	CHEBI:31225 ;
ChEMBL	ChEMBL277474 ;
CompTox Dashboard (EPA)	DTXSID6021117 ;
ECHA InfoCard	100.000.442
Chemical and physical data
Formula	C11H12N2O
Molar mass	188.230 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1C=C(C)N(C)N1c2ccccc2;
	InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 ; Key:VEQOALNAAJBPNY-UHFFFAOYSA-N ;
	(verify)

Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), antipyrin,^[1] or analgesine) is an analgesic (pain reducing), antipyretic (fever reducing) and anti-inflammatory drug. While it predates the term, it is often classified as a nonsteroidal anti-inflammatory drug (NSAID). Phenazone was one of the earliest synthetic medications — when it was patented in 1883, the only synthetic medical chemicals on the market were chloral hydrate, a sedative (as well as at least one derivative of that chemical), trimethylamine, and iodol (tetraiodopyrrol), an early antiseptic.^[2] One of the earliest widely used analgesics and antipyretics, phenazone was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen. However, it is still available in several countries either as an over-the-counter or prescribed drug.

^ Jennings, Oscar (11 Jan 1890). "Antipyrin and the Prevailing Epidemic". The Lancet. 135 (3463): 105–106. doi:10.1016/S0140-6736(02)13571-9.
^ Arny, H. V. (1926-09-01). "The Evolution of Synthetic Medicinal Chemicals". Industrial & Engineering Chemistry. 18 (9): 949–952. doi:10.1021/ie50201a027. Retrieved 2022-08-11.

[1] Jennings, Oscar (11 Jan 1890). "Antipyrin and the Prevailing Epidemic". The Lancet. 135 (3463): 105–106. doi:10.1016/S0140-6736(02)13571-9.

[EvoSynthMed-2] Arny, H. V. (1926-09-01). "The Evolution of Synthetic Medicinal Chemicals". Industrial & Engineering Chemistry. 18 (9): 949–952. doi:10.1021/ie50201a027. Retrieved 2022-08-11.

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