CHEBI:2922 - auranofin

ChEBI IDCHEBI:2922
ChEBI Nameauranofin
Stars
DefinitionAn S-glycosyl compound consisting of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose with the sufur atom coordinated to (triethylphosphoranylidene)gold. It is administered orally for the treatment of active progressive rheumatoid arthritis.
Last Modified25 February 2013
DownloadsMolfile
FormulaC20H34AuO9PS
Net Charge0
Average Mass678.491
Monoisotopic Mass678.13268
SMILESCC[P+](CC)(CC)[Au-][S][C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
InChIInChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1
InChIKeyAUJRCFUBUPVWSZ-XTZHGVARSA-M
Wikipedia
Roles Classification
Biological Roles:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
EC 1.8.1.9 (thioredoxin reductase) inhibitor  An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of thioredoxin reductase (EC 1.8.1.9).
Applications:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
ChEBI Ontology
Outgoing Relation(s)
auranofin (CHEBI:2922) has role antirheumatic drug (CHEBI:35842)
auranofin (CHEBI:2922) has role EC 1.8.1.9 (thioredoxin reductase) inhibitor (CHEBI:64670)
auranofin (CHEBI:2922) has role immunosuppressive agent (CHEBI:35705)
auranofin (CHEBI:2922) is a S-glycosyl compound (CHEBI:35275)
auranofin (CHEBI:2922) is a gold coordination entity (CHEBI:33971)
IUPAC Name 
(2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-κS1)(triethylphosphine)gold
INNs  Source
auranofinKEGG DRUG
auranofinaChemIDplus
auranofineChemIDplus
auranofinumChemIDplus
Synonyms  Source
(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetateChemIDplus
2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)goldChemIDplus
Triethylphosphine goldChemIDplus
Brand Name  Source
RidauraKEGG DRUG
Manual XrefsDatabases
AuranofinWikipedia
D00237KEGG DRUG
DB00995DrugBank
DE2051495Patent
US3635945Patent
Registry NumbersSources
Gmelin:112479Gmelin
Reaxys:11644694Reaxys
Reaxys:14401468Reaxys
Gmelin:294107Gmelin
Beilstein:8187029Beilstein
CAS:34031-32-8KEGG DRUG
CAS:34031-32-8ChemIDplus
CAS:34031-32-8DrugBank
Citations