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.^[1] 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. ^[2]

Adverse effects

Possible adverse effects include:

Opioids
See also: Opioids template

Opium & alkaloids thereof	Codeine^# • Morphine^# • Opium • Laudanum • Paregoric

Semi-synthetic opium derivatives	Acetyldihydrocodeine • Benzylmorphine • Buprenorphine • Desomorphine • Dihydrocodeine • Dihydromorphine • Ethylmorphine • Diamorphine • Hydrocodone • Hydromorphinol • Hydromorphone • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone

Synthetic opioids	Alphaprodine • Anileridine • Butorphanol • Dextromoramide • Dextropropoxyphene • Dezocine • Fentanyl • Ketobemidone • Levorphanol • Methadone • Meptazinol • Nalbuphine • Pentazocine • Propoxyphene • Propiram • Pethidine • Phenazocine • Piminodine • Piritramide • Tapentadol • Tilidine • Tramadol

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class	Fenoprofen • Flurbiprofen • Ibuprofen^# • Ketoprofen • Naproxen • Oxaprozin

Oxicam class	Meloxicam • Piroxicam

Acetic acid class	Diclofenac • Indometacin • Ketorolac • Nabumetone • Sulindac • Tolmetin

COX-2 inhibitors	Celecoxib • Rofecoxib • Valdecoxib • Parecoxib • Lumiracoxib

Anthranilic acid (fenamate) class	Meclofenamate • Mefenamic acid

Salicylates	Aspirin (Acetylsalicylic acid)^# • Benorylate • Diflunisal • Ethenzamide • Magnesium salicylate • Salicin • Salicylamide • Salsalate • Trisalate • Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneous

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

Lidocaine • Cocaine • Phenazone

anat(e/p)/phys/devp

noco/cong, epon

proc, drug(S2)