Structure via PubChem · Public domain (PubChem)
diacerein
Sign in to saveDiacerein (INN), also known as diacetylrhein, is a slow-acting medicine of the class anthraquinone used to treat joint diseases such as osteoarthritis. It works by inhibiting interleukin-1 beta. An updated 2014 Cochrane review found diacerein had a small beneficial effect on pain. Diacerein-containing medications are registered in some European Union and Asian countries and included as a treatment option on several international therapeutic guidelines.
Chemical data
- Formula
- C19H12O8
- Molecular weight
- 368.3 g/mol
- IUPAC name
- 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
- SMILES
- CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O
- InChIKey
- TYNLGDBUJLVSMA-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 124 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- rheumatic disease, rheumatoid arthritis, osteoarthritis, hip, gout
via ChEMBL · EBI
Research
491 papers- Diacerein.Drugs · 1997
- Diacerein for osteoarthritis.The Cochrane database of systematic reviews · 2014
- Diacerein: Recent insight into pharmacological activities and molecular pathways.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2020
- Diacerein for osteoarthritis.The Cochrane database of systematic reviews · 2006
- [Diacerein].Annali italiani di medicina interna : organo ufficiale della Societa italiana di medicina interna · 1986
via PubMed
Wikidata facts
- Subclass of
- carboxylic acid
- Mass
- 368.053
Show 4 more facts
- chemical formula
- C₁₉H₁₂O₈
- canonical SMILES
- CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C=C(C=C3C2=O)C(=O)O)OC(=O)C
- subject has role
- anti-inflammatory agent
- Commons category
- Diacerein
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
7 sectionsContents
- Synthesis
- Pharmacology
- Side effects
- Special warning
- Dosage and administration
- See also
- References
Diacerein (INN), also known as diacetylrhein, is a slow-acting medicine of the class anthraquinone used to treat joint diseases such as osteoarthritis. It works by inhibiting interleukin-1 beta. An updated 2014 Cochrane review found diacerein had a small beneficial effect on pain. Diacerein-containing medications are registered in some European Union and Asian countries and included as a treatment option on several international therapeutic guidelines.
==Synthesis== Various synthetic routes to diacerein have been developed, most of which utilize aloin as a precursor. The hydroxyl groups of aloin are acetylated, and the intermediates are subsequently oxidized using chromic anhydride in an acetic acid solvent system..
Excerpted from Wikipedia’s “diacerein” article, available under the CC BY-SA 4.0 licence.