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auranofin (CHEBI:2922)

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ChEBI Name auranofin
ChEBI ID CHEBI:2922
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C20H34AuO9PS ChEBI
Net Charge 0
Average Mass 678.48400
InChI
InChI=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
InChIKey
AUJRCFUBUPVWSZ-XTZHGVARSA-M
SMILES
CC[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
Roles Classification
Chemical Role(s): 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).
Biological Role(s): 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).
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.
Application(s): 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.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
auranofin KEGG DRUG
auranofina ChemIDplus
auranofine ChemIDplus
auranofinum ChemIDplus
Synonyms Sources
(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate ChemIDplus
2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold ChemIDplus
Triethylphosphine gold ChemIDplus
Brand Name Source
Ridaura KEGG DRUG
Database Links Databases
Auranofin Wikipedia
D00237 KEGG DRUG
DB00995 DrugBank
DE2051495 Patent
US3635945 Patent
View more database links
Registry Numbers Types Sources
112479 Gmelin Registry Number Gmelin
11644694 Reaxys Registry Number Reaxys
14401468 Reaxys Registry Number Reaxys
294107 Gmelin Registry Number Gmelin
34031-32-8 CAS Registry Number KEGG DRUG
34031-32-8 CAS Registry Number DrugBank
34031-32-8 CAS Registry Number ChemIDplus
8187029 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10796461 PubMed citation CiteXplore
11071118 PubMed citation CiteXplore
16036347 PubMed citation CiteXplore
17645497 PubMed citation CiteXplore
18409052 PubMed citation CiteXplore
18789312 PubMed citation CiteXplore
20127591 PubMed citation CiteXplore
22610278 PubMed citation CiteXplore
2656613 PubMed citation CiteXplore
6426843 PubMed citation CiteXplore
6426923 PubMed citation CiteXplore
9189058 PubMed citation CiteXplore
Last Modified
25 febrero 2013

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