Auranofin

Base Information

• Chemical Name: Auranofin
• CAS No.: 34031-32-8
• Molecular Formula: C20H34 Au O9 P S
• Molecular Weight: 678.54
• European Community (EC) Number: 251-801-9
• UNII: 3H04W2810V
• Metabolomics Workbench ID: 145722
• NCI Thesaurus Code: C65242
• Pharos Ligand ID: G2N5K15UW5RL
• RXCUI: 1227
• Wikidata: Q421230
• Wikipedia: Auranofin
• Mol file: 34031-32-8.mol

Synonyms:Auranofin;Crisinor;Ridaura;Ridauran;SK and F 39162;SK and F D 39162;SK and F-39162;SK and F39162

Chemical Property of Auranofin

Chemical Property:

• Appearance/Colour: Needles.
• Melting Point: 103 - 105ºC
• Boiling Point: 425.5°Cat760mmHg
• Flash Point: 298°C
• PSA: 149.54000
• Density: g/cm³
• LogP: 2.79250
• Storage Temp.: room temp
• Solubility.: DMSO: ≥5mg/mL
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 678.132686
• Heavy Atom Count: 32
• Complexity: 532

Purity/Quality:

99% ^*data from raw suppliers

Auranofin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
• Isomeric SMILES: CCP(CC)CC.CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
• Recent ClinicalTrials: Sirolimus and Auranofin in Treating Patients With Advanced or Recurrent Non-Small Cell Lung Cancer or Small Cell Lung Cancer
• Recent EU Clinical Trials: A proof of concept clinical trial assessing the safety of the coordinated undermining of survival paths by 9 repurposed drugs combined with metronomic temozolomide (CUSP9v3 Treatment Protocol) for recurrent glioblastoma
• Recent NIPH Clinical Trials: Auranofin clinical trial for desmoid
• Description: Auranofin is the first orally effective gold compound to be marketed for the treatment of severe rheumatoid arthritis. It is better tolerated and more convenient than gold sodium thiomalate, which is administered intramuscularly.
• Uses: Auranofin is a new oral gold-based antiarthritis drug. Auranofin inhibits various leukocyte activation pathways at multiple sites. Auranofin inhibits the release of inflammatory mediators from human m acrophages, basophils, and pulmonary mast cells. Auranofin is an efficient inducer of mitochondrial membrane permeability transition pore in the presence of calcium ions related to its inhibition of m itochondrial thioredoxin reductase. Auranofin inhibits both leukocyte activation pathways at multiple sites and the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Auranofin also inhibits 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5 and selenoenzyme thioredoxin reductase (TrxR) which is involved in the defense against oxidative stress. Auranofin is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.
• Clinical Use: Auranofin is indicated in adults with active rheumatoid arthritis who have not responded sufficiently to one or more NSAIDs.