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Penicillamine



Penicillamine
Systematic (IUPAC) name
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
Identifiers
CAS number 52-67-5
ATC code M01CC01
PubChem 5852
DrugBank APRD01171
Chemical data
Formula C5H11NO2S 
Mol. mass 149.212 g/mol
Pharmacokinetic data
Bioavailability Variable
Metabolism Hepatic
Half life 1 hour
Excretion Renal
Therapeutic considerations
Pregnancy cat.

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Legal status

Unregulated

Routes  ?

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.

Additional recommended knowledge

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.

Penicillamine is also used for treatment of scleroderma.

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 increased cystine excretion, penicillamine binds with the cystine to make it more soluble.
  • Penicillamine has been used to treat mercury poisoning.

History

Dr John Walshe (1956) first described the use of penicillamine in Wilson's disease. 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 (Walshe 2003).

References

  • Walshe JM. Penicillamine, a new oral therapy for wilson's disease. Am J Med. 1956;21:487-95. PMID 13362281.
  • Walshe JM. The story of penicillamine: a difficult birth. Mov Disord 2003;18:853-9. PMID 12889074.

Acetic acid derivatives and related substances (Indometacin, Sulindac, Tolmetin, Zomepirac, Diclofenac, Alclofenac, Bumadizone, Etodolac, Lonazolac, Fentiazac, Acemetacin, Difenpiramide, Oxametacin, Proglumetacin, Ketorolac, Aceclofenac, Bufexamac)

Oxicams (Piroxicam, Tenoxicam, Droxicam, Lornoxicam, Meloxicam)

Propionic acid derivatives (Ibuprofen, Naproxen, Ketoprofen, Fenoprofen, Fenbufen, Benoxaprofen, Suprofen, Pirprofen, Flurbiprofen, Indoprofen, Tiaprofenic acid, Oxaprozin, Ibuproxam, Dexibuprofen, Flunoxaprofen, Alminoprofen, Dexketoprofen)

Fenamates (Mefenamic acid, Tolfenamic acid, Flufenamic acid, Meclofenamic acid)

Coxibs (Celecoxib, Rofecoxib, Valdecoxib, Parecoxib, Etoricoxib, Lumiracoxib)

other anti-inflammatory and antirheumatic agents, non-steroids (Nabumetone, Niflumic acid, Azapropazone, Glucosamine, Benzydamine, Glucosaminoglycan polysulfate, Proquazone, Orgotein, Nimesulide, Feprazone, Diacerein, Morniflumate, Tenidap, Oxaceprol, Chondroitin sulfate)
Specific antirheumatic agentsQuinolines (Oxycinchophen) - Gold preparations (Sodium aurothiomalate, Sodium aurothiosulfate, Auranofin, Aurothioglucose, Aurotioprol) - Penicillamine/Bucillamine
  This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Penicillamine". A list of authors is available in Wikipedia.
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