diacerein   Click here for help

GtoPdb Ligand ID: 10800

Synonyms: Artrodar® | Fisiodar®
Approved drug
diacerein is an approved drug
Compound class: Synthetic organic
Comment: Diacerein is a prodrug which is metabolized to rhein. It has anti-inflammatory activity via antagonism of the interleukin-1 receptor. It is an anthraquinone type compound and growth-inhibitory effects of diacerein have been shown against various drug-resistant staphylococcal strains [2].

diacerein is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 124.04
Molecular weight 368.05
XLogP 2.29
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
Isomeric SMILES CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
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)
InChI Key TYNLGDBUJLVSMA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Diacerein is not approved by the FDA or the EMA, but has been granted marketing authorisation by regulatory agencies in a number of countries. It is used to treat osteoarthritis, but this use is limited by its propensity to cause severe diarrhea. Clinical trials in other conditions are ongoing.
Orphan designation for the treatment of epidermolysis bullosa was issued by the EMA in May 2019 [1].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04351100 Efficacy of Diacerein on Ocular Surface Disease in Degenerative Arthritis Patients Observational Chulalongkorn University
NCT03389308 Long Term Open-label Study Evaluating Safety of Diacerein 1% Ointment Topical Formulation in Subjects With Epidermolysis Bullosa Simplex Phase 2 Interventional Castle Creek Pharmaceuticals, LLC
NCT02242149 Efficacy Study of Diacerein on Glycemic Control and Liver Fat in Type 2 Diabetes Subjects Phase 3 Interventional Universidade Federal do Rio de Janeiro
NCT02060552 Immune Molecular and Inflammatory Cytokines Dysfunction Analysis in Gout Patients With Different Urate Levels Phase 4 Interventional Tongji Hospital