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Penicillamine
File:Penicillamine structure.png
190px
Systematic (IUPAC) name
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
Clinical data
Pregnancy
category
  • D (Aust.)
Routes of
administration		 Oral
Legal status
Legal status
  • Prescription
Pharmacokinetic data
Bioavailability Variable
Metabolism Hepatic
Biological half-life 1 hour
Excretion Renal
Identifiers
CAS Number 52-67-5
ATC code M01CC01 (WHO)
PubChem CID 5852
DrugBank APRD01171
Chemical data
Formula C5H11NO2S
Molar mass 149.212 g/mol[[Script error: No such module "String".]]
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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.

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 2nd line treatment for arsenic poisonning, after dimercaprol (BAL)

Adverse effects

Adverse effects include:

History

Dr. John Walshe (1956) first described the use of penicillamine in Wilson's disease.[4] 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.[5]

References

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External links

Specific antirheumatic products / DMARDs (M01C)
Quinolines
Gold preparations
Other
Iron
Copper
Penicillamine#
Lead
Thallium
Other/ungrouped
ALA · BAPTA · DTPA · DMPS · DMSA · EGTA
# = WHO-EM
de:Penicillamin

es:Penicilamina it:Penicillamina ja:D-ペニシラミン pl:Penicylamina pt:Penicilamina ro:Penicilamina

ru:Пеницилламин
  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. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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