[(2R,4S,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5}-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

• ChemBase ID: 868
• Molecular Formular: C20H34AuO9PS
• Molecular Mass: 678.483871
• Monoisotopic Mass: 678.1326833
• SMILES: S([C@@H]1O[C@@H](C(OC(=O)C)[C@H](OC(=O)C)C1OC(=O)C)COC(=O)C)[Au]=P(CC)(CC)CC
• Canonical SMILES: CCP(=[Au]S[C@@H]1O[C@H](COC(=O)C)C([C@@H](C1OC(=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
• InChIKey: AUJRCFUBUPVWSZ-SVGYNJBSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4S,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5}-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,4S,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5}-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate
• Brand Name: Ridaura
• Synonyms: Auroafen; Auranofin

Database IDs

• CAS Number: 34031-32-8
• PubChem SID: 160964331
• PubChem CID: 0

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.0203
• LogD (pH = 7.4): -1.0203
• Log P: -1.0203
• Molar Refractivity: 114.885 cm^3
• Polarizability: 54.109283 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.99
• LOG S: -3.65
• Solubility (Water): 1.51e-01 g/l

DETAILS

DrugBank - DB00995

• Drug Groups: approved
• Description: Auranofin is a organogold compound classified by the World Health Organization as an antirheumatic agent. Auranofin appears to induce heme oxygenase 1 (HO-1) mRNA. Heme oxygenase 1 is an inducible heme-degrading enzyme with anti-inflammatory properties.
• Indication: Used in the treatment of active, progressive or destructive forms of inflammatory arthritis, such as adult rheumatoid arthritis.
• Pharmacology: Auranofin is a gold salt used in treating inflammatory arthritis. Gold salts are called second-line drugs because they are often considered when the arthritis progresses in spite of antiinflammatory drugs (NSAIDs and corticosteroids).
• Toxicity: Oral, rat: LD₅₀ = > 2000 mg/kg. Symptoms of overdose may include diarrhoea, vomiting, abdominal cramps, and symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing).
• Affected Organisms: Humans and other mammals
• Elimination: Approximately 60% of the absorbed gold (15% of the administered dose) from a single dose of auranofin is excreted in urine; the remainder is excreted in the feces.
• References: Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. [Pubmed] ; Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. [Pubmed] ; Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. [Pubmed] ; Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. [Pubmed] ; Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

REFERENCES

• Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. Pubmed
• Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. Pubmed
• Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. Pubmed
• Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. Pubmed
• Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. Pubmed