Antipyrine

Title: Antipyrine
CAS Registry Number: 60-80-0
CAS Name: 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
Additional Names: 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; phenazone; 1,5-dimethyl-2-phenyl-3-pyrazolone; phenyldimethylpyrazolon(e); dimethyloxychinizin; dimethyloxyquinazine; oxydimethylquinizine
Trademarks: Analgesine; Anodynine; Parodyne; Phenylone; Sedatine
Molecular Formula: C11H12N2O
Molecular Weight: 188.23
Percent Composition: C 70.19%, H 6.43%, N 14.88%, O 8.50%
Literature References: Prepn: Müller et al., Monatsh. Chem. 89, 23 (1958); Hagers Handb. Pharm. Praxis Vol. 6 (Springer Verlag, Berlin, 1977) p 571. Toxicity: Hart, J. Pharmacol. Exp. Ther. 89, 205 (1947). Metabolism: H. Uchino et al., Xenobiotica 13, 155 (1983). Clinical comparison with paracetamol: H. Quiding et al., Int. J. Oral Surg. 11, 304 (1982). Use as indicator of hepatic drug metabolism: E. S. Vessel, Clin. Pharm. Ther. 26, 275 (1979); G. C. Farrell, L. Zaluzny, Br. J. Clin. Pharmacol. 18, 559 (1984). HPLC determn in urine: E. Brendel et al., J. Pharm. Biomed. Anal. 7, 1783 (1989). Clinical pharmacokinetics: H. A. Ali et al., Hum. Exp. Toxicol. 13, 658 (1994).
Properties: Tabular crystals or white powder; slightly bitter taste. mp 111-113°. One gram dissolves in less than 1 ml water, 1.3 ml alcohol, 1 ml chloroform, 43 ml ether. The aq soln is neutral to litmus. LD50 orally in rats: 1.8 g/kg (Hart).
Melting point: mp 111-113°
Toxicity data: LD50 orally in rats: 1.8 g/kg (Hart)
Derivative Type: Acetylsalicylate
CAS Registry Number: 569-84-6
Trademarks: Acetopyrine; Acopyrine; Acetasol
Molecular Formula: C20H20N2O5
Molecular Weight: 368.38
Percent Composition: C 65.21%, H 5.47%, N 7.60%, O 21.72%
Properties: Crystals, mp 63-65°. One part dissolves in 400 parts of water, in 20 parts of 2% aq sod. bicarbonate soln. Freely sol in hot water, cold alc, chloroform; sparingly sol in ether. Note: Not to be confused with antipyrine salicylacetate.
Melting point: mp 63-65°
Derivative Type: Mandelate
CAS Registry Number: 603-64-5
Additional Names: Antipyrine amygdalate
Molecular Formula: C11H12N2O.C8H8O3
Molecular Weight: 340.37
Percent Composition: C 67.05%, H 5.92%, N 8.23%, O 18.80%
Properties: Cryst powder, mp 52-55°. One gram dissolves in 15 ml water, 4 ml alc, 26 ml ether.
Melting point: mp 52-55°
Derivative Type: Methylethylglycolate
CAS Registry Number: 5794-16-1
Additional Names: Antipyrine 2-hydroxy-2-methylbutyrate
Trademarks: Astrolin
Molecular Formula: C16H22N2O4
Molecular Weight: 306.36
Percent Composition: C 62.73%, H 7.24%, N 9.14%, O 20.89%
Properties: Crystalline powder, mp 64-65.5°. Soluble in water, alc.
Melting point: mp 64-65.5°
Derivative Type: Salicylacetate
CAS Registry Number: 603-59-8
Additional Names: a-Carboxy-o-anisic acid compd with antipyrine
Trademarks: Pyrosal
Molecular Formula: C20H20N2O6
Molecular Weight: 384.38
Percent Composition: C 62.49%, H 5.24%, N 7.29%, O 24.97%
Properties: Crystals, mp 149-150°. Bitter, acid taste. Sparingly soluble in water; soluble in alc. Note: Not to be confused with antipyrine acetylsalicylate.
Melting point: mp 149-150°
Therap-Cat: Analgesic.
Therap-Cat-Vet: Has been used as an antipyretic, analgesic and in laminitis of horses.
Keywords: Analgesic (Non-Narcotic).
Antipyrine Salicylate Antireticular Cytotoxic Serum Antivenin (Crotalidae) Polyvalent Antivenin (Latrodectus mactans) Antivirin

Antipyrine
Phenazone.svg
Systematic (IUPAC) name
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
Clinical data
Legal status  ?
Identifiers
CAS number 60-80-0 YesY
ATC code N02BB01 S02DA03
PubChem CID 2206
DrugBank DB01435
ChemSpider 2121 YesY
UNII T3CHA1B51H YesY
KEGG D01776 YesY
ChEBI CHEBI:31225 YesY
ChEMBL CHEMBL277474 YesY
Synonyms analgesine, antipyrine
Chemical data
Formula C11H12N2O 
Mol. mass 188.226 g/mol
 YesY (what is this?)  (verify)

Phenazone (INN; also known as phenazon, antipyrine (USAN), or analgesine) is an analgesic, a non-steroidal anti-inflammatory drug and an 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]