9009. Suxibuzone

Nomenclature

CAS number: 27470-51-5
Butanedioic acid mono[(4-butyl-3,5-dioxo-1,2-diphenyl-4-pyrazolidinyl)methyl] ester; succinic acid monoester with 4-butyl-4-(hydroxymethyl)-1,2-diphenyl-3,5-pyrazolidinedione; 4-butyl-4-(hydroxymethyl)-1,2-diphenyl-3,5-pyrazolidinedione hydrogen succinate (ester); 1,2-diphenyl-4-n-butyl-4-hydroxymethyl-3,5-dioxopyrazolidine hemisuccinate; 4-hydroxymethylbutazolidine hemisuccinate; AE-17; Calibène (Delalande); Danilon (Esteve); Flogos (Gentili); Solurol (Delalande).
C24H26N2O6; mol wt 438.47.
C 65.74%, H 5.98%, N 6.39%, O 21.89%.

Description and references

Prodrug of phenylbutazone, q.v. Prepd (not claimed) and use as anti-inflammatory: A. Esteve, DE 1936747; idem, US 3752894 (1970, 1973 both to Lab. Esteve). Pharmacology: A. Esteve et al., Quim. Ind. (Madrid) 17, 107 (1971). HPLC determn in plasma and urine: T. Marunaka et al., J. Pharm. Sci. 69, 1258 (1980). Metabolism in humans: Y. Yasuda et al., ibid. 71, 565 (1982). Comparative clinical study with phenylbutazone in rheumatoid arthritis: Y. Mizushima et al., Int. J. Tissue React. 5, 35 (1983).

Chemical structure

Properties

White, bitter crystalline powder from alcohol, mp 126-127°. Sol in most organic solvents. Insol in water. LD50 orally in mice: 5.683 micromol/kg (Esteve, 1973).

Therapeutic Category

Anti-inflammatory.

Therapeutic Category (Veterinary)

Analgesic, antipyretic, anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Pyrazolones