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

• ChemBase ID: 737
• Molecular Formular: C5H11NO2S
• Molecular Mass: 149.21134
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
• IUPAC Traditional name: depen; penicillamine
• Brand Name: Artamine; Cuprenil; Cuprimine; Cupripen; Depamine; Depen; Distamine; Kuprenil; Mercaptovaline; Mercaptyl; Metalcaptase; Pendramine; Perdolat; Sufirtan; Trolovol
• Synonyms: 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; 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

Database IDs

• CAS Number: 52-67-5
• EC Number: 200-148-8
• MDL Number: MFCD00064302
• Beilstein Number: 1722375
• Merck Index: 147088
• PubChem SID: 160964200; 24886985; 24898564
• PubChem CID: 5852
• CHEBI ID: 7959
• ATC CODE: M01CC01
• CHEMBL: 1430
• Chemspider ID: 5643
• DrugBank ID: DB00859
• KEGG ID: D00496
• Unique Ingredient Identifier: GNN1DV99GX
• Wikipedia Title: Penicillamine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.555553
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.1465738
• LogD (pH = 7.4): -2.1542492
• Log P: -2.1465182
• Molar Refractivity: 37.225 cm^3
• Polarizability: 15.067698 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.7
• LOG S: -1.51
• Solubility (Water): 4.65e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.11E+005 mg/L; Methanol; Water
• Apperance: White Solid
• Melting Point: 202-204°C dec.; 207-210°C (dec.); 210 °C (dec.)(lit.); 211 - 213°C; 214-217 °C (dec.)
• Optical Rotation: [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)
• Hydrophobicity(logP): -1.729; -1.9

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: YV9425000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Variable
• Excretion: Renal
• Half Life: 1 hour
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: D (Australia); D (US)
• Gene Information: mouse ... Oprk1(18387)

Product Information

• Purity: ≥99%; ≥99.0% (NT); 95%; 98-101%; 99%
• Ignition Residue: ≤0.05%
• Linear Formula: (CH3)2C(SH)CH(NH2)CO2H

DETAILS

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.

REFERENCES

• 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)