化合物信息

ID:868

基本信息

化学结构

分子式

C₂₀H₃₄AuO₉PS

分子量

678.483871

精确质量

678.1326833

电荷

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

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

-1.0203

LogD (pH = 7.4)

-1.0203

Log P

-1.0203

摩尔折射率

114.885

极化性

54.109283

极化表面积

114.43

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

2.99

LOG S

-3.65

溶解度

1.51e-01 g/l

数据来源

学术数据

DrugBank

DB00995

PubChem

数据来源

名称和标识

别名

AuroafenAuranofin

商标名

Ridaura

IUPAC标准名

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

IUPAC传统名

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

名称和标识

数据登录号

PubChem SID

160964331

PubChem CID

CAS号

34031-32-8

数据登录号

化合物性质

暂无数据

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分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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]

描述信息

参考文献

PubChem文献

数据源提供

• 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

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

• ALOGPS 2.1

数据来源

• 学术数据

名称和标识

• 别名

• 商标名

• IUPAC标准名

• IUPAC传统名

数据登录号

• PubChem SID

• PubChem CID

• CAS号

• DrugBank

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

学术数据

DrugBank

DB00995

PubChem

别名

AuroafenAuranofin

IUPAC标准名

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

IUPAC传统名

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

PubChem SID

160964331

DrugBank

DB00995

Drug Groups

approved

Description

Indication

Used in the treatment of active, progressive or destructive forms of inflammatory arthritis, such as adult rheumatoid arthritis.

Pharmacology

Toxicity

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]

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

External Links

• [Wikipedia]

• [PDRhealth]

• [Drugs.com]

数据源提供

• 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