Diacerein

Title: Diacerein
CAS Registry Number: 13739-02-1
CAS Name: 4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid
Additional Names: 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate; 1,8-diacetoxy-3-carboxyanthraquinone; diacerhein; diacetylrhein; DAR
Manufacturers' Codes: SF-277
Trademarks: Artrodar (Proter); Fisiodar (Abiogen)
Molecular Formula: C19H12O8
Molecular Weight: 368.29
Percent Composition: C 61.96%, H 3.28%, O 34.75%
Literature 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).
Properties: Yellow plates from acetic acid, mp 217-218°.
Melting point: mp 217-218°
Therap-Cat: Antiarthritic.
Keywords: Antiarthritic/Antirheumatic.
Diacetazotol Diacetin Diacetonamine Diacetone Acrylamide Diacetone Alcohol

Diacerein
Diacerein.svg
Systematic (IUPAC) name
4,5-diacetyloxy-9,10-dioxo-anthracene-2-
carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. Lacking information
Legal status  ?
Routes Oral
Pharmacokinetic data
Protein binding 99%
Metabolism Hepatic: deacetylation to rhein, later glucuronidation and sulfate conjugation
Half-life 4 to 5 hours
Excretion Renal (30%)
Identifiers
CAS number 13739-02-1 YesY
ATC code M01AX21
PubChem CID 26248
ChemSpider 24456 YesY
UNII 4HU6J11EL5 YesY
KEGG D07270 YesY
ChEMBL CHEMBL41286 YesY
Synonyms Diacetylrhein; Diacerhein; 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-; 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, diacetate; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate
Chemical data
Formula C19H12O8 
Mol. mass 368.294 g/mol
 YesY (what is this?)  (verify)

Diacerein (INN), also known as diacetylrhein, is a drug used in the treatment of osteoarthritis.[1] It works by inhibiting interleukin-1. A 2005 Cochrane review found diacerein to be slightly, but significantly, more effective than placebo in improving pain and slowing the progress of osteoarthritis in the hip.[2]