716. Antipyrine
Nomenclature
CAS number: 60-80-0
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; phenazone; 1,5-dimethyl-2-phenyl-3-pyrazolone; phenyldimethylpyrazolon(e); dimethyloxychinizin; dimethyloxyquinazine; oxydimethylquinizine; Analgesine; Anodynine; Parodyne; Phenylone; Sedatine. C11H12N2O; mol wt 188.23.
C 70.19%, H 6.43%, N 14.88%, O 8.50%.
Description and 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. Pharmacol. 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).Derivative
Acetylsalicylate.Nomenclature
CAS number: 569-84-6
Acetopyrine; Acopyrine; Acetasol. C20H20N2O5; mol wt 368.38.
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.Derivative
Mandelate.Nomenclature
CAS number: 603-64-5
Antipyrine amygdalate. C11H12N2O.C8H8O3; mol wt 340.37.
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.Derivative
Methylethylglycolate.Nomenclature
CAS number: 5794-16-1
Antipyrine 2-hydroxy-2-methylbutyrate; Astrolin. C16H22N2O4; mol wt 306.36.
C 62.73%, H 7.24%, N 9.14%, O 20.89%.
Properties
Crystalline powder, mp 64-65.5°. Soluble in water, alc.Derivative
Salicylacetate.Nomenclature
CAS number: 603-59-8
α-Carboxy-o-anisic acid compd with antipyrine; Pyrosal. C20H20N2O6; mol wt 384.38.
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.Therapeutic Category
Analgesic.
Therapeutic Category (Veterinary)
Has been used as an antipyretic, analgesic and in laminitis of horses.Keywords
Analgesic; Non-opioids; Pyrazolones