Penicillamine

Penicillamine
Systematic (IUPAC) name
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
Clinical data
Trade names Cuprimine
AHFS/Drugs.com monograph
Pregnancy cat. D (Aust.)
Legal status Prescription
Routes Oral
Pharmacokinetic data
Bioavailability Variable
Metabolism Hepatic
Half-life 1 hour
Excretion Renal
Identifiers
CAS number 52-67-5 YesY
ATC code M01CC01
PubChem CID 5852
DrugBank APRD01171
ChemSpider 5643 YesY
UNII GNN1DV99GX YesY
KEGG D00496 YesY
ChEBI CHEBI:7959 YesY
ChEMBL CHEMBL1430 YesY
Chemical data
Formula C5H11NO2S 
Mol. mass 149.212 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Penicillamine is a pharmaceutical of the chelator class. It is sold under the trade names of Cuprimine and Depen. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine). It is a metabolite of penicillin, although it has no antibiotic properties.

Contents

Uses

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.

It is used as a chelating agent:

  • In Wilson's disease, a rare genetic disorder of copper metabolism, penicillamine treatment relies on its binding to accumulated copper and elimination through urine.
  • In cystinuria, a hereditary disorder featuring formation of cystine stones, penicillamine binds with cysteine to yield a mixed disulfide which is more soluble than cystine.
  • Penicillamine has been used to treat scleroderma
  • Penicillamine is the second line treatment for arsenic poisoning, after dimercaprol (BAL)

Adverse effects

Adverse effects include:

History

Dr. John Walshe (1956) first described the use of penicillamine in Wilson's disease.[5] He had discovered the compound in the urine of patients (including himself) who had taken penicillin, and experimentally confirmed that it increased urinary copper excretion by chelation. He had initial difficulty convincing several world experts of the time (Drs Denny Brown and Cumings) of its efficacy, as they held that Wilson's disease was not primarily a problem of copper homeostasis but of amino acid metabolism, and that dimercaprol should be used as a chelator. Later studies confirmed both the copper-centered theory and the efficacy of D-penicillamine. Walshe also pioneered other chelators in Wilson's such as triethylene tetramine, 2HCl, and tetrathiomolybdate.[6]

References

  1. ^ Table 14-2 in: Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson. Robbins Basic Pathology. Philadelphia: Saunders. ISBN 1-4160-2973-7.  8th edition.
  2. ^ Robbins and Cotran, Pathological Basis of Disease 8th Edition, Kumar et al
  3. ^ Bolognia, Jean; et al (2007). Dermatology. Philadelphia: Elsevier. ISBN 1416029990. 2nd edition.
  4. ^ Underwood, J. C. E. (2009). General and systemic Pathology. Elsevier Limited. ISBN 9780443068898. 
  5. ^ Walshe JM (January 1956). "Wilson's disease; new oral therapy". Lancet 267 (6906): 25–6. doi:10.1016/S0140-6736(56)91859-1. PMID 13279157. 
  6. ^ Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074. 

External links


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Look at other dictionaries:

  • Penicillamine — Pen i*cil lam*ine, n. (Chem., Med.) a substance ({C5H11NO2S}) which is a degradation product of the penicillins. Chemically it is 3 mercapto D valine. It has chelating properties and is used in medicine as an antirheumatic and to chelate copper… …   The Collaborative International Dictionary of English

  • pénicillamine — ● pénicillamine nom féminin Médicament antirhumatismal et chélateur (efficace contre les intoxications) …   Encyclopédie Universelle

  • penicillamine — [pen΄i sil′ə mēn΄, pen΄i sil′əmin] n. a white, crystalline chelating drug, C5H11NO2S, used to treat Wilson s disease, severe cases of rheumatoid arthritis, etc …   English World dictionary

  • penicillamine — A degradation product of penicillin; a chelating agent used in the treatment of lead poisoning, hepatolenticular degeneration, and cystinuria, and in the removal of excess copper in Wilson …   Medical dictionary

  • penicillamine — penicilaminas statusas T sritis chemija formulė (CH₃)₂C(SH)CH(NH₂)COOH atitikmenys: angl. penicillamine rus. пеницилламин ryšiai: sinonimas – 2 amino 3 merkapto 3 metilbutano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • penicillamine — noun Etymology: penicillin + amine Date: 1943 an amino acid C5H11NO2S that is obtained from penicillins and is used especially in the treatment of cystinuria, rheumatoid arthritis, and poisoning by metals (as copper or lead) …   New Collegiate Dictionary

  • penicillamine — (= dimethyl cysteine) Product of acid hydrolysis of penicillin that chelates heavy metals (lead, copper, mercury) and assists in their excretion in cases of poisoning. Also used in treatment of rheumatoid arthritis although its mode of action as… …   Dictionary of molecular biology

  • penicillamine — /pen euh sil euh meen , min/, n. Pharm. a chelating agent, C5H11NO2S, produced by the degradation of penicillin, used in the treatment of severe rheumatoid arthritis and in heavy metal poisoning. [1940 45; PENICILL(IN) + AMINE] * * * …   Universalium

  • penicillamine — noun a breakdown product of penicillin used as a chelating drug to treat poisoning by heavy metals etc …   Wiktionary

  • penicillamine — pen·i·cil·la·mine …   English syllables

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