6916. Oxametacine

Nomenclature

CAS number: 27035-30-9
1-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-acetamide; 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetohydroxamic acid; indoxamic acid; Dinulcid (Pharmascience); Flogar (UCB).
C19H17ClN2O4; mol wt 372.80.
C 61.21%, H 4.60%, Cl 9.51%, N 7.51%, O 17.17%.

Description and references

Deriv of indomethacin, q.v. Prepn: R. Aries, FR 1599495 (1969), C.A. 73, 3797h (1970); F. De Martiis et al., DE 2008332 corresp to US 3624103 (both 1971 to ABC); eidem, Boll. Chim. Farm. 114, 309 (1975). Pharmaco-toxicological evaluation: eidem, ibid. 319. Disposition in rats: L. F. Elsom et al., Arzneim.-Forsch. 29, 1155 (1979). Pharmacokinetics: P. Dittrich et al., ibid. 31, 518 (1981). Effect on prostaglandin biosynthesis: J. S. Franzone et al., Farmaco Ed. Sci. 35, 498 (1980). Clinical study: J. Polderman, M. Colon, J. Int. Med. Res. 8, 156 (1980).

Chemical structure

Properties

Cryst from dioxane, mp 181-182° (dec). Sol in most organic solvents at elevated temperatures. In strong alkali it is hydrolyzed quickly to the debenzoylated product. LD50 orally in rats: 96 mg/kg (De Martiis, U.S. patent).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives