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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.	D (Aust.)
Legal status	Prescription
Routes	Oral
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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.

[edit] 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 mercury poisoning.

[edit] Adverse effects

Adverse effects include:

Glomerulonephritis ^[1]
Antibody-mediated myasthenic syndrome which may persist event after its withdrawal.
Drug-induced systemic lupus erythematosus
Elastosis perforans serpiginosa Bolognia, Jean; et al (2007). Dermatology. Philadelphia: Elsevier. ISBN 1416029990. 2nd edition.

[edit] History

Dr. John Walshe (1956) first described the use of penicillamine in Wilson's disease.^[2] 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.^[3]

[edit] References

^ Table 8-5 in: Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson. Robbins Basic Pathology. Philadelphia: Saunders. ISBN 1-4160-2973-7. 8th edition.
^ 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.
^ Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074.

[edit] External links

Penicillamine (Systemic) - Medlineplus.org
Penicillamine and Arthritis - Medicinenet.com

[Kumar8-5-0] Table 8-5 in: Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson. Robbins Basic Pathology. Philadelphia: Saunders. ISBN 1-4160-2973-7. 8th edition.

[Walshe1956-1] 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.

[2] Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074.

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Contents

[edit] Uses

[edit] Adverse effects

[edit] History

[edit] References

[edit] External links