Diacerein

Diacerein

Clinical data
Other names	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
AHFS/Drugs.com	International Drug Names
Pregnancy category	Lacking information
Routes of administration	Oral
ATC code	M01AX21 (WHO)
Pharmacokinetic data
Protein binding	99%
Metabolism	Hepatic: deacetylation to rhein, later glucuronidation and sulfate conjugation
Elimination half-life	4 to 5 hours
Excretion	Renal (30%)
Identifiers
IUPAC name 4,5-diacetyloxy-9,10-dioxo-anthracene-2- carboxylic acid
CAS Number	13739-02-1 Y
PubChem CID	26248
DrugBank	DB11994 Y
ChemSpider	24456 Y
UNII	4HU6J11EL5
KEGG	D07270 Y
ChEMBL	ChEMBL41286 Y
CompTox Dashboard (EPA)	DTXSID4045636
ECHA InfoCard	100.033.904
Chemical and physical data
Formula	C19H12O8
Molar mass	368.297 g·mol−1
3D model (JSmol)	Interactive image
Solubility in water	Practically insoluble in water 0.01 mg/mL (20 °C)
SMILES O=C(Oc3cccc2C(=O)c1cc(cc(OC(=O)C)c1C(=O)c23)C(=O)O)C
InChI InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25) Y Key:TYNLGDBUJLVSMA-UHFFFAOYSA-N Y
(verify)

Diacerein (INN), also known as diacetylrhein, is a slow-acting medicine of the class anthraquinone used to treat joint diseases such as osteoarthritis (swelling and pain in the joints).^[1] It works by inhibiting interleukin-1 beta. An updated 2014 Cochrane review found diacerein had a small beneficial effect on pain.^[2] Diacerein-containing medications are registered in some European Union and Asian countries^[which?] and included as a treatment option on several international therapeutic guidelines.^{[which?][citation needed]}