Phenazone

Antipyrine

Systematic (IUPAC) name
1,2-dihydro- 1,5-dimethyl- 2-phenyl- 3H-pyrazol- 3-one
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	60-80-0 Y
ATC code	N02BB01 S02DA03
PubChem	CID 2206
DrugBank	DB01435
ChemSpider	2121 Y
UNII	T3CHA1B51H Y
KEGG	D01776 Y
ChEBI	CHEBI:31225 Y
ChEMBL	CHEMBL277474 Y
Synonyms	analgesine, antipyrine
Chemical data
Formula	C11H12N2O
Mol. mass	188.226 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 Y Key:VEQOALNAAJBPNY-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Phenazone (INN), phenazon, antipyrine (USAN), or analgesine is an analgesic and antipyretic. It was first synthesized by Ludwig Knorr in 1883. It is formed by reducing diortho- dinitrodiphenyl with sodium amalgam and methyl alcohol, or by heating diphenylene-ortho-dihydrazine with hydrochloric acid to 150 °C. It crystallizes in needles which melt at 156 °C. Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid. Phenazone has an elimination half life of about 12 hours.

Adverse effects

Possible adverse effects include:^{[citation needed]}

• Allergy to pyrazolones
• Nausea
• Agranulocytosis
• Hepatotoxicity

See also

• Propyphenazone
• A/B Otic Drops, ear drops combined with benzocaine to relieve pain and remove cerumen