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D-penicillamine

Penicillamine
Penicillamine structure.svg
D-Penicillamine-3D-balls.png
Clinical data
Trade names Cuprimine, Cuprenyl, Depen, others
AHFS/Drugs.com Monograph
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
Routes of
administration
by mouth (capsules)
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability Variable
Metabolism liver
Biological half-life 1 hour
Excretion kidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.136
Chemical and physical data
Formula C5H11NO2S
Molar mass 149.212 g/mol
3D model (Jmol)
  

Penicillamine, sold under the trade names of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease. It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, copper poisoning, and lead poisoning. It is taken by mouth.

Common side effects include rash, loss of appetite, nausea, diarrhea, and low blood white blood cell levels. Other serious side effects include liver problems, obliterative bronchiolitis, and myasthenia gravis. It is not recommended in people with lupus erythematosus. Use during pregnancy may result in harm to the baby. Penicillamine works by binding heavy metals such that they can be removed from the body in the urine.

Penicillamine was approved for medical use in the United States in 1970. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.55 to 1.20 USD a dose. In the United States treatment costs more than 200 USD per month.

It is used as a chelating agent:

Penicillamine can be used as a disease-modifying antirheumatic drug (DMARD) to treat severe active rheumatoid arthritis in patients who have failed to respond to an adequate trial of conventional therapy, although it is rarely used today due to availability of TNF inhibitors and other agents, such as and tofacitinib. Penicillamine works by reducing numbers of T-lymphocytes, inhibiting macrophage function, decreasing IL-1, decreasing rheumatoid factor, and preventing collagen from cross-linking.


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