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

• ChemBase编号: 737
• 分子式: C5H11NO2S
• 平均质量: 149.21134
• 单一同位素质量: 149.0510496
• SMILES: SC([C@@H](N)C(=O)O)(C)C
• Canonical SMILES: N[C@H](C(S)(C)C)C(=O)O
• 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
• IUPAC传统名: depen; penicillamine
• 商标名: Artamine; Cuprenil; Cuprimine; Cupripen; Depamine; Depen; Distamine; Kuprenil; Mercaptovaline; Mercaptyl; Metalcaptase; Pendramine; Perdolat; Sufirtan; Trolovol
• 别名: D-(-)-青霉胺; 3,3-二甲基-D-半胱氨酸; 3-巯基-D-缬氨酸; D-(-)-2-氨基-3-巯基-3-甲基丁酸; D-青霉胺; 3,3-Dimethyl-D-cysteine; 3-Mercapto-D-valine; D-(-)-2-Amino-3-mercapto-3-methylbutanoic acid; (S)-2-amino-3-mercapto-3-methylbutanoic acid; D-(-)-Penicillamine; (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid; (2S)-2-Amino-3-methyl-3-sulfanylbutanoic Acid; (S)-3,3-Dimethylcysteine; Cuprenil; Cuprimine; Cupripen; D-3-Mercaptovaline; Depamine; Depen; Kuprenil; Mercaptyl; Metalcaptase; NSC 81549; D-Penicillamine; beta,beta-Dimethylcysteine; beta-Thiovaline; D-Mercaptovaline; D-Penamine; D-Penicilamine; D-Penicillamine; D-Penicyllamine; Dimethylcysteine; L-Penicillamine; PCA; Penicilamina [INN-Spanish]; Penicillamin; Penicillamina [DCIT]; Penicillaminum [INN-Latin]; Penicilllamine; Penicillamine; D-Penicillamine

登记号

• CAS号: 52-67-5
• EC号: 200-148-8
• MDL号: MFCD00064302
• Beilstein号: 1722375
• 默克索引号: 147088
• PubChem SID: 24886985; 160964200; 24898564
• PubChem CID: 5852
• CHEBI ID: 7959
• ATC码: M01CC01
• CHEMBL: 1430
• Chemspider ID: 5643
• DrugBank ID: DB00859
• KEGG ID: D00496
• 美国药典/FDA物质标识码: GNN1DV99GX
• 维基百科标题: Penicillamine

理论计算性质

JChem

• Acid pKa: 2.555553
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.1465738
• LogD (pH = 7.4): -2.1542492
• Log P: -2.1465182
• 摩尔折射率: 37.225 cm^3
• 极化性: 15.067698 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.7
• LOG S: -1.51
• 溶解度: 4.65e+00 g/l

分子性质

理化性质

• 溶解度: 1.11E+005 mg/L; Methanol; Water
• 外观: White Solid
• 熔点: 202-204°C dec.; 207-210°C (dec.); 210 °C (dec.)(lit.); 211 - 213°C; 214-217 °C (dec.)
• 比旋光度: [α]20/D -63±2°, c = 1% in 1 M NaOH; [α]24/D -62.0°, c = 0.5 in 1 M NaOH; -63 (c=1 in 1N NaOH)
• 疏水性(logP): -1.729; -1.9

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• RTECS编号: YV9425000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P280G-P305+P351+P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 生物利用度: Variable
• 排泄: Renal
• 半衰期: 1 hour
• 代谢: Hepatic
• 法定药品分级: Rx-only
• 妊娠期药物分类: D (Australia); D (US)
• 相关基因信息: mouse ... Oprk1(18387)

产品相关信息

• 纯度: ≥99%; ≥99.0% (NT); 95%; 98-101%; 99%
• 燃烧残渣: ≤0.05%
• 线性分子式: (CH3)2C(SH)CH(NH2)CO2H

详细说明

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

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.

Toronto Research Chemicals - P223000

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

参考文献

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