1483. Bumadizone

Nomenclature

CAS number: 3583-64-0
2-Butylpropanedioic acid-1-(1,2-diphenylhydrazide); butylmalonic acid mono(1,2-diphenylhydrazide); N-(2-carboxycaproyl)hydrazobenzene; α-carboxycaproyl-N,N′-diphenylhydrazine.
C19H22N2O3; mol wt 326.39.
C 69.92%, H 6.79%, N 8.58%, O 14.71%.

Description and references

Non-steriodal anti-inflammatory drug (NSAID). Prepn: NL 6406412; Pfister et al., US 3455999 (1964, 1969 to Geigy); NL 6600685 (1966 to Byk-Gulden). Main product of the hydrolysis of phenylbutazone, q.v.: Schmid, Helv. Chim. Acta 53, 2239 (1970). Chemical characterization: Pawelczyk, Wachowiak, Acta Pol. Pharm. 26, 433 (1969), C.A. 72, 136355p (1970). Series of articles on pharmacology: Arzneim.-Forsch. 23, 1226-1251, 1813-1822 (1973). Toxicity: R. Riedel, W. Schoetensack, ibid. 1215.

Chemical structure

Properties

Crystals from ether-petr ether, mp 116-117°. Also reported as mp 77-79° (dependent on speed of crystallization). uv max (0.1N NaOH): 234, 264 nm (ε 16200, 3700).

Derivative

Calcium salt hemihydrate.

Nomenclature

CAS number: 69365-73-7
Desflam (Merck KGaA); Eumotol (Byk Gulden).
C38H42CaN4O6.H2O; mol wt 699.85.
C 65.21%, H 6.19%, Ca 5.73%, N 8.01%, O 14.86%.

Properties

Dec 154°. Sol in chloroform, alcohol, ether. Slightly sol in water. LD50 in mice, rats (mg/kg): 2500, 1250 orally; 258, 263 i.v. (Riedel, Schoetensack).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylbutyric Acid Derivatives