Diacerein

Diacerein
Structural formula of diacerein
Ball-and-stick model of the diacerein molecule
Clinical data
Other namesDiacetylrhein; 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.comInternational Drug Names
Pregnancy
category
  • Lacking information
Routes of
administration
Oral
ATC code
Pharmacokinetic data
Protein binding99%
MetabolismHepatic: deacetylation to rhein, later glucuronidation and sulfate conjugation
Elimination half-life4 to 5 hours
ExcretionRenal (30%)
Identifiers
  • 4,5-diacetyloxy-9,10-dioxo-anthracene-2-
    carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.033.904 Edit this at Wikidata
Chemical and physical data
FormulaC19H12O8
Molar mass368.297 g·mol−1
3D model (JSmol)
Solubility in waterPractically insoluble in water 0.01 mg/mL (20 °C)
  • O=C(Oc3cccc2C(=O)c1cc(cc(OC(=O)C)c1C(=O)c23)C(=O)O)C
  • 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) checkY
  • Key:TYNLGDBUJLVSMA-UHFFFAOYSA-N checkY
  (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]

  1. ^ Gouvas H (2011). Use of Sodium Hyaluronate in the treatment of Osteoarthritis. Greece.{{cite book}}: CS1 maint: location missing publisher (link)
  2. ^ Fidelix TS, Macedo CR, Maxwell LJ, Fernandes Moça Trevisani V (February 2014). "Diacerein for osteoarthritis". The Cochrane Database of Systematic Reviews (2): CD005117. doi:10.1002/14651858.CD005117.pub3. PMC 10712695. PMID 24515444.