2960. Diacerein

Nomenclature

CAS number: 13739-02-1
4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid; 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate; 1,8-diacetoxy-3-carboxyanthraquinone; diacerhein; diacetylrhein; DAR; SF-277; Artrodar (Proter); Fisiodar (Abiogen).
C19H12O8; mol wt 368.29.
C 61.96%, H 3.28%, O 34.75%.

Description and references

Diacetyl derivative of rhein, q.v. Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Prepn: A. Tschirch, K. Heuberger, Arch. Pharm. 240, 596 (1902); V. K. Murty et al., Tetrahedron 23, 515 (1967). Effect on prostaglandin release: P. Pomarelli et al., Farmaco Ed. Sci. 35, 836 (1980). Inhibition of proteases: L. Raimondi et al., Pharmacol. Res. Commun. 14, 103 (1982). Use in arthritis: C. A. Friedmann, DE 2711493; idem, US 4244968 (1977, 1981 both to Proter). Preliminary clinical study in osteoarthritis: A. G. Kay et al., Curr. Med. Res. Opin. 6, 548 (1980). Use in multiple sclerosis, amyotrophic lateral sclerosis: C. A. Friedmann, US 4346103 (1982); idem, JP Kokai 83 225015 (1983 to Proter), C.A. 100, 144991e (1984). Clinical trial in osteoarthritis: S. Adami et al., Clin. Ter. 112, 439 (1985).

Chemical structure

Properties

Yellow plates from acetic acid, mp 217-218°.

Therapeutic Category

Antiarthritic.

Keywords

Antiarthritic/Antirheumatic