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Product Description
Mechanism of action
Auranofin is an oral gold(I) complex containing triethylphosphine and thioglucose ligands, classically classified as a disease-modifying antirheumatic drug (DMARD). Its mechanism is multifactorial: auranofin inhibits various thiol-dependent enzymes, modulates redox balance by affecting glutathione and thioredoxin systems and suppresses pro-inflammatory cytokine production. It also impairs phagocytosis and antigen processing in macrophages.
Benefits and advantages
In contemporary research, auranofin is used beyond rheumatology as a tool compound in redox biology, thioredoxin reductase inhibition studies, and investigations into antimicrobial and anticancer applications tied to thiol–gold interactions. It serves as a prototype for metal-based immunomodulatory and anticancer drugs.
Side effects and risks
Potential toxicities include diarrhoea, stomatitis, dermatitis, proteinuria, thrombocytopenia and rare but serious bone-marrow suppression or nephrotic syndrome. Gold accumulation in tissues necessitates careful dose control in clinical use. In raw-material form, auranofin must be handled as a cytotoxic and immunomodulatory metal complex with appropriate containment and waste disposal.
Datasheet
| Molecular Formula | C32H46AuO9PS |
|---|---|
| Molecular Weight | 678.5 g/mol |
| CAS Number | 34031-32-8 |
| Storage Condition | Commercially available auranofin capsules should be stored in tight, light-resistant containers at 153 °C. |
| Solubility | Insoluble in water |
| Purity | Purity information is available upon request (COA). |
| Synonym | AURANOFIN; SK&F-39162; Auranofina; Auranofine; Auranofinum |
| IUPAC/Chemical Name | gold(1+);(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphane |
| InChl Key | AUJRCFUBUPVWSZ-XTZHGVARSA-M |
| InChl Code | 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 |
| References |
3D Conformer.
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