Details of the Drug

General Information of Drug (ID: DMN2Q5I)

Drug Name
Diacerein
Synonyms
Diacerein; 13739-02-1; Diacetylrhein; Diacerhein; Fisiodar; Artrodar; 1,8-DIACETOXY-3-CARBOXYANTHRAQUINONE; DIACERIN; 4,5-Diacetylrhein; Diacereinum [Latin]; Diacereine [French]; Diacereina [Spanish]; UNII-4HU6J11EL5; Diacerein [INN]; SF-277; C19H12O8; EINECS 237-310-2; BRN 2184909; 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid; MLS000028577; 4HU6J11EL5; 1,8-Diacetoxyanthraquinone-3-carboxylic acid; Diacerein (INN); 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid; NCGC00018274-04; SMR000058958; AK468692
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 368.3
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Bioavailability
The bioavailability of drug is 5% []
Clearance
The renal clearance of drug is 0.1 L/h [1]
Elimination
37% of drug excreted in urine and 53% of drug in feces as estimated in rats [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 4 - 10 hours [1]
Metabolism
The drug is metabolized via the double deacetylation to rhien [1]
Vd
The volume of distribution (Vd) of drug is 15-60 L [1]
Chemical Identifiers
Formula
C19H12O8
IUPAC Name
4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
Canonical SMILES
CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=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)
InChIKey
TYNLGDBUJLVSMA-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
26248
ChEBI ID
CHEBI:94708
CAS Number
13739-02-1
DrugBank ID
DB11994
TTD ID
D0N1FS

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Interleukin-1 beta (IL1B) TTRYK0X IL1B_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aggrecan core protein (ACAN) OTUOCW8K PGCA_HUMAN Gene/Protein Processing [4]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [4]
Collagen alpha-1(II) chain (COL2A1) OT5E59C8 CO2A1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Interleukin-1 beta (IL1B) DTT IL1B 4.74E-01 8.78E-03 0.02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pharmacokinetics of diacerein. Clin Pharmacokinet. 1998 Nov;35(5):347-59.
2 De Witte P, Lemli J: Excretion and distribution of [14C]rhein and [14C]rhein anthrone in rat. J Pharm Pharmacol. 1988 Sep;40(9):652-5.
3 Non-surgical treatment of osteoarthritis of large joints - new aspects. Wien Med Wochenschr. 2009;159(3-4):76-86.
4 Comparison between chondroprotective effects of glucosamine, curcumin, and diacerein in IL-1beta-stimulated C-28/I2 chondrocytes. Osteoarthritis Cartilage. 2008 Oct;16(10):1205-12. doi: 10.1016/j.joca.2008.01.013. Epub 2008 Mar 5.