auranofin   Click here for help

GtoPdb Ligand ID: 6306

Synonyms: Ridaura® | SK&F-39162 | SK-39162
Approved drug Immunopharmacology Ligand
auranofin is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Auranofin is a gold-containing complex, antirheumatic agent.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 0
Rotatable bonds 15
Topological polar surface area 139.73
Molecular weight 678.13
XLogP 2.93
No. Lipinski's rules broken 1
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Canonical SMILES CC[P+]([Au-]SC1OC(COC(=O)C)C(C(C1OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
Isomeric SMILES CC[P+]([Au-]S[C@@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
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
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Summary of Clinical Use Click here for help
Auranofin is a gold-containing medicine used for the management of rheumatoid arthritis in patients who do not respond to or are intolerant of other medicines.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Drug treatment decreases levels of rheumatoid factors and immunoglobulins, potentially via inhibition of the selenoenzyme, thioredoxin reductase [1] which has been shown to suppress the pro-inflammatory NLRP3/interleukin-1β pathway.
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