CAS 52-67-5|Penicillamine|depen|Cuprimine|(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|3,3-Dimethyl-D-c...

General Information

Structure

Molecular Formula

C₅H₁₁NO₂S

Molecular Mass

149.21134

Exact Mass

149.0510496

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

-2.26

LogD (pH = 5.5)

-2.15

Log P

-2.15

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

2.56

Polar Surface Area

63.32

Polarizability

14.75

Molar Refractivity

37.23

LOG S

-1.54

Data Source

Names and Identifiers

Brand Name

CuprimineDepenPerdolatCuprenilDistamineTrolovolPendramineArtamineMetalcaptaseCupripenSufirtanMercaptylKuprenilMercaptovalineDepamineD-Penamine

Synonyms

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(S)-2-amino-3-mercapto-3-methylbutanoic acid3,3-Dimethyl-D-cysteineD-PenicillamineD-(-)-2-氨基-3-巯基-3-甲基丁酸3-Mercapto-D-valineD-MercaptovalineD-PenicillamineDepenPenicilamina [INN-Spanish]PCAMetalcaptaseCupripenD-3-MercaptovalinePenicilllamineD-Penicillaminebeta,beta-DimethylcysteineDepamineCupriminePenicillamin(S)-3,3-DimethylcysteineL-PenicillamineKuprenilPenicillaminum [INN-Latin](2S)-2-Amino-3-methyl-3-sulfanylbutanoic AcidDimethylcysteineD-PenicyllamineD-PenicilamineNSC 81549(2S)-2-amino-3-methyl-3-sulfanylbutanoic acidD-PenamineMercaptylPenicillamina [DCIT]beta-ThiovalineCuprenilD-(-)-PenicillamineD-(-)-青霉胺D-(-)-penicillamineD-beta,beta-dimethylcysteineD-penicillamine(S)-3,3-dimethylcysteine3-mercapto-D-valine(S)-2-amino-3-mercapto-3-methylbutanoic acidPA(-)-penicillamine

IUPAC Traditional name

depen penicillamine

IUPAC name

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

API Name

Penicillamine

International Nonproprietary Name (INN)

penicillaminepenicilaminapenicillaminum

Names and Identifiers

Registration numbers

CAS Number

CHEMBL

PubChem CID

KEGG ID

Unique Ingredient Identifier

Chemspider ID

Wikipedia Title

ATC CODE

CHEBI ID

7959CHEBI:469179CHEBI:7959

PubChem SID

248869852489856416096420056352880

MDL Number

Beilstein Number

EC Number

Merck Index

DrugBank ID

MetaboLights Database

MTBLS1693MTBLS804

UniProt Database

P43477Q9XBQ8Q76KX0O50078C3K630Q9DA79Q9H4B8P31428Q8C255P16444Q75SP7Q5M872P31429Q4R7M2Q5U2X4Q9H4A9P22412Q3SZM7P31430

Patent number

WO2006098761US2006205705US2007225339EP1705184WO2005021547WO2007117394WO2005023761EP1738759WO2007087637EP1815867US2007207191EP1990048US2007243132US2005075333WO2007135242

HMDB Database

HMDB0014997

BindingDB Database

39346

Reaxys Registry

1722375

PubMed Citation Links

23200399104089682216927413793949199047292337525122151785719623118570451170991716736232242089723342748226833362207673221989991

BRENDA Ligand Database

Protein Data Bank

SABIO-RK Database

BKMS React Database

Drug Central Database

2,081

PDBeChem Database

LEI

ArrayExpress (Gene Expression Altlas)

E-GEOD-2825

KEGG DRUG Database

D00496

ACToR Database

16414-54-31113-41-352-67-5

IEDB Database

113237

SureChEMBL Database

SCHEMBL4343

CompTox Database

DTXSID6037069

Registration numbers

Properties

Related Proteins

PDB Bank

3H5G

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

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

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

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

CuprimineDepenPerdolatCuprenilDistamineTrolovolPendramineArtamineMetalcaptaseCupripenSufirtanMercaptylKuprenilMercaptovalineDepamineD-Penamine

Synonyms

IUPAC Traditional name

depen penicillamine

IUPAC name

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

API Name

Penicillamine

International Nonproprietary Name (INN)

penicillaminepenicilaminapenicillaminum

Registration numbers

CAS Number

CHEMBL

PubChem CID

KEGG ID

Unique Ingredient Identifier

Chemspider ID

Wikipedia Title

ATC CODE

CHEBI ID

7959CHEBI:469179CHEBI:7959

PubChem SID

248869852489856416096420056352880

MDL Number

Beilstein Number

EC Number

Merck Index

DrugBank ID

MetaboLights Database

MTBLS1693MTBLS804

UniProt Database

P43477Q9XBQ8Q76KX0O50078C3K630Q9DA79Q9H4B8P31428Q8C255P16444Q75SP7Q5M872P31429Q4R7M2Q5U2X4Q9H4A9P22412Q3SZM7P31430

Patent number

WO2006098761US2006205705US2007225339EP1705184WO2005021547WO2007117394WO2005023761EP1738759WO2007087637EP1815867US2007207191EP1990048US2007243132US2005075333WO2007135242

HMDB Database

HMDB0014997

BindingDB Database

39346

Reaxys Registry

1722375

PubMed Citation Links

23200399104089682216927413793949199047292337525122151785719623118570451170991716736232242089723342748226833362207673221989991

BRENDA Ligand Database

Protein Data Bank

SABIO-RK Database

BKMS React Database

Drug Central Database

2,081

PDBeChem Database

LEI

ArrayExpress (Gene Expression Altlas)

E-GEOD-2825

KEGG DRUG Database

D00496

ACToR Database

16414-54-31113-41-352-67-5

IEDB Database

SureChEMBL Database

CompTox Database

Related Proteins

Molecule Details

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.

References

PubChem Literature

From Data Sources

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

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

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

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

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:737