CAS 34031-32-8|Auranofin|Auroafen|[(2R,4S,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5}-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate|[(2R,4S,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5...

General Information

Structure

Molecular Formula

C₂₀H₃₄AuO₉PS

Molecular Mass

678.483871

Exact Mass

678.1326833

Charge

0

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

Canonic 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

Isomeric 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

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

Polarizability

54.109283

Polar Surface Area

114.43

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

Data Source

Academic Data

DrugBank

DB00995

PubChem

0

Data Source

Names and Identifiers

Synonyms

AuroafenAuranofin

Brand Name

Ridaura

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

Names and Identifiers

Registration numbers

PubChem SID

160964331

PubChem CID

0

CAS Number

34031-32-8

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. 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

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:868