CAS 52-67-5|Cuprimine|Penicillamine|depen|(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid|3,3-二甲基-D-半胱氨酸|D-(-)-2-Amino-3-mercapto-3-methylbutanoic acid|D-青霉胺|3-巯基-D-缬氨酸|(S)-2-amino-3-me...

基本信息

化学结构

分子式

C₅H₁₁NO₂S

分子量

149.21134

精确质量

149.0510496

电荷

InChI

InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

InChIKey

VVNCNSJFMMFHPL-VKHMYHEASA-N

Canonic Smiles

N[C@H](C(S)(C)C)C(=O)O

Isomeric Smiles

SC([C@@H](N)C(=O)O)(C)C

计算属性

JChem

LogD (pH = 7.4)

-2.26

LogD (pH = 5.5)

-2.15

Log P

-2.15

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

2.56

极化表面积

63.32

极化性

14.75

摩尔折射率

37.23

LOG S

-1.54

数据来源

名称和标识

别名

Penicillamine3,3-二甲基-D-半胱氨酸D-(-)-2-Amino-3-mercapto-3-methylbutanoic acidD-青霉胺3-巯基-D-缬氨酸3,3-Dimethyl-D-cysteine(S)-2-amino-3-mercapto-3-methylbutanoic acidD-PenicillamineD-(-)-2-氨基-3-巯基-3-甲基丁酸3-Mercapto-D-valinePCAD-MercaptovalineD-PenicillaminePenicilllamineCupripenDepenPenicilamina [INN-Spanish]MetalcaptaseD-3-MercaptovalineD-Penicillaminebeta,beta-DimethylcysteinePenicillaminum [INN-Latin]DepamineDimethylcysteinePenicillamin(S)-3,3-DimethylcysteineL-PenicillamineKuprenilD-Penicyllamine(2S)-2-Amino-3-methyl-3-sulfanylbutanoic AcidCuprimineD-Penaminebeta-Thiovaline(2S)-2-amino-3-methyl-3-sulfanylbutanoic acidMercaptylPenicillamina [DCIT]NSC 81549CuprenilD-PenicilamineD-(-)-青霉胺D-(-)-PenicillamineD-beta,beta-dimethylcysteineD-(-)-penicillamine(S)-3,3-dimethylcysteineD-penicillamine(-)-penicillaminePA(S)-2-amino-3-mercapto-3-methylbutanoic acid3-mercapto-D-valine

IUPAC传统名

depen penicillamine

商标名

CuprimineCuprenilTrolovolPerdolatDepenDistamineCupripenArtamineMetalcaptasePendramineKuprenilMercaptylMercaptovalineDepamineSufirtanD-Penamine

IUPAC标准名

(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

API名称

Penicillamine

国际非专利药品(INN)

penicilaminapenicillaminepenicillaminum

名称和标识

数据登录号

化合物性质

分子相关蛋白质

PDB Bank

3H5G

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00859

Drug Groups

approved

Description

3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. [PubChem]

Indication

For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.

Pharmacology

Penicillamine is a chelating agent used in the treatment of Wilson's disease. It is also used to reduce cystine excretion in cystinuria and to treat patients with severe, active rheumatoid arthritis unresponsive to conventional therapy. Penicillamine is used as a form of immunosuppression to treat rheumatoid arthritis. It works by reducing numbers of T-lymphocytes, inhibiting macrophage function, decreasing IL-1, decreasing rheumatoid factor, and preventing collagen from cross-linking. Its use in Wilson's disease, a rare genetic disorder of copper metabolism, relies on its binding to accumulated copper and elimination through urine.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

rapidly but incompletely

Half Life

1 hour

Protein Binding

>80% (bound to plasma proteins)

Elimination

Excretion is mainly renal, mainly as disulfides.

References

• WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. [Pubmed]

• Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. [Pubmed]

• Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. [Pubmed]

• Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. [Pubmed]

• Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Penicillamine

Sigma Aldrich

P4875

包装
5, 25 g in poly bottle
Application
It is used as an antirheumatic and as a chelating agent in Wilson′s disease. It is used as a copper chelator to form mixed disulfides with cysteine or other sulfide media components. It is used to inactivate protein-1 DNA binding1 and to inhibit the growth of asynchronous cultures of rabbit articular chondrocytes2.
Biochem/physiol Actions
Penicillamine is a haracteristic degradation product of penicillin type antibiotics. One atom of copper combines with two molecules of penicillamine. Penicillamine reduces excess cystine excretion in cystinuria. This is by disulfide interchange between penicillamine and cystine, which results in formation of a readily excreted penicillamine-cysteine disulfide. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. Penicillamine lowers IgM rheumatoid factor and depresses T-cell activity.

TRC

P223000

A Penicillin metabolite used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

ChEBI

CHEBI:7959

An optically active form of penicillamine having D-configuration. Pharmaceutical form (L-form is toxic) of chelating agent used to treat heavy metal poisoning.

描述信息

参考文献

PubChem文献

数据源提供

• Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. Pubmed

• Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. Pubmed

• Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. Pubmed

• Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. Pubmed

• WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. Pubmed

• Marti-Prats, L., et al.: Neurosci. Lett., 483, 143 (2010)

• Singh, A., et al.: J. Pharm. Sci., 99, 3931 (2010)

• Everette, J., et al.: J. Agric. Food Chem., 58, 8139 (2010)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

depen penicillamine

商标名

CuprimineCuprenilTrolovolPerdolatDepenDistamineCupripenArtamineMetalcaptasePendramineKuprenilMercaptylMercaptovalineDepamineSufirtanD-Penamine

IUPAC标准名

(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

API名称

Penicillamine

国际非专利药品(INN)

penicilaminapenicillaminepenicillaminum

分子相关蛋白质

PDB Bank

3H5G

描述信息

DrugBank

DB00859

Drug Groups

approved

Description

3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. [PubChem]

Indication

For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

rapidly but incompletely

Half Life

1 hour

Protein Binding

>80% (bound to plasma proteins)

Elimination

Excretion is mainly renal, mainly as disulfides.

References

• WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. [Pubmed]

• Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. [Pubmed]

• Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. [Pubmed]

• Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. [Pubmed]

• Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

P4875

P223000

A Penicillin metabolite used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

ChEBI

CHEBI:7959

An optically active form of penicillamine having D-configuration. Pharmaceutical form (L-form is toxic) of chelating agent used to treat heavy metal poisoning.

参考文献

PubChem文献

数据源提供

• Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. Pubmed

• Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. Pubmed

• Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. Pubmed

• Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. Pubmed

• WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. Pubmed

• Marti-Prats, L., et al.: Neurosci. Lett., 483, 143 (2010)

• Singh, A., et al.: J. Pharm. Sci., 99, 3931 (2010)

• Everette, J., et al.: J. Agric. Food Chem., 58, 8139 (2010)

生物活性

PubChem BioAssay

化合物性质

化合物信息

ID:737