Home > Compound List > Product Information
Penicillamine_Molecular_structure_CAS_52-67-5)
Click picture or here to close

Penicillamine

Catalog No. DB00859 Name DrugBank
CAS Number 52-67-5 Website http://www.ualberta.ca/
M. F. C5H11NO2S Telephone (780) 492-3111
M. W. 149.21134 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 737

SYNONYMS

IUPAC name
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
IUPAC Traditional name
penicillamine
Brand Name
Perdolat
Kuprenil
Depen
Artamine
Cuprimine
Cupripen
Distamine
Mercaptovaline
Sufirtan
Cuprenil
Depamine
Mercaptyl
Metalcaptase
Pendramine
Trolovol
Synonyms
Dimethylcysteine
beta-Thiovaline
D-Penicyllamine
D-Penamine
D-Penicilamine
PCA
Penicillaminum [INN-Latin]
beta,beta-Dimethylcysteine
D-Mercaptovaline
D-Penicillamine
L-Penicillamine
Penicilamina [INN-Spanish]
Penicillamin
Penicillamina [DCIT]
Penicilllamine

DATABASE IDS

CAS Number 52-67-5

PROPERTIES

Hydrophobicity(logP) -1.9
Solubility 1.11E+005 mg/L

DETAILS

Description (English)
Item Information
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

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