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Penicillamine

Clinical data
Trade names	Cuprimine
AHFS/Drugs.com	Monograph
Pregnancy category	D (Aust.)
Routes of administration	Oral
ATC code	M01CC01 (WHO)
Legal status
Legal status	Prescription
Pharmacokinetic data
Bioavailability	Variable
Metabolism	Hepatic
Elimination half-life	1 hour
Excretion	Renal
Identifiers
IUPAC name (2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
CAS Number	52-67-5
PubChem CID	5852
DrugBank	DB00859
ChemSpider	5643
UNII	GNN1DV99GX
KEGG	D00496
ChEBI	CHEBI:7959
ChEMBL	ChEMBL1430
CompTox Dashboard (EPA)	DTXSID6037069
ECHA InfoCard	100.000.136
Chemical and physical data
Formula	C5H11NO2S
Molar mass	149.212 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES CC(C)((C(=O)O)N)S
InChI InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1 Key:VVNCNSJFMMFHPL-VKHMYHEASA-N
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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 second line treatment for arsenic poisoning, after dimercaprol (BAL)

Adverse effects

Adverse effects include:

• Membranous glomerulonephritis
• Aplastic anemia (idiosyncratic)
• Antibody-mediated myasthenic syndrome, which may persist even after its withdrawal
• Drug-induced systemic lupus erythematosus
• Elastosis perforans serpiginosa
• Toxic myopathies

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.

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.{{cite book}}: CS1 maint: multiple names: authors list (link) 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. {{cite book}}: Explicit use of et al. in: |author= (help)2nd edition.
4. Underwood, J. C. E. (2009). General and systemic Pathology. Elsevier Limited. ISBN 9780443068898.
5. Walshe JM (1956). "Wilson's disease; new oral therapy". Lancet. 267 (6906): 25–6. doi:10.1016/S0140-6736(56)91859-1. PMID 13279157. {{cite journal}}: Unknown parameter |month= ignored (help)
6. Walshe JM (2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074. {{cite journal}}: Unknown parameter |month= ignored (help)

External links

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

• Enantiopure drugs
• Amino acids
• Chelating agents
• Antirheumatic products
• Thiols
• World Health Organization essential medicines