Penicillamine

Information about Penicillamine

Penicillamine is chelating agent used to decrease copper stores in Wilson disease, which also has immunomodulatory activity in rheumatic diseases such as rheumatoid arthritis, scleroderma and systemic lupus erythematosus.

Liver safety of Penicillamine

Penicillamine is capable of causing hypersensitivity reactions, some of which are accompanied by liver injury which is typically cholestatic.

Mechanism of action of Penicillamine

Penicillamine (pen" i sil' a meen) is d-isomer of dimethylcysteine, a breakdown product of penicillin, which was originally isolated from the urine of patients with liver disease receiving penicillin. It was later found to have chelating properties against copper and used in Wilson disease. Penicillamine was also found to lower levels of immune complexes, which led to its use in several rheumatic and immune disorders such as rheumatoid arthritis, scleroderma, systemic lupus erythematosus and primary biliary cirrhosis.

FDA approval information for Penicillamine

Penicillamine was approved for use in Wilson disease in 1960 and is still widely used for that rare indication. The use of penicillamine for rheumatic disorders has decreased markedly with the availability of more modern, potent and less toxic agents.

Dosage and administration for Penicillamine

Penicillamine is available in generic forms and under the brand names of Cuprimine and Depen in capsules of 125 and 250 mg and tablets of 250 mg. The usual dose in 250 mg four times daily, increasing based upon effect and tolerance to a maximum of 2 grams daily. Lower doses were used in rheumatic diseases. Common side effects include gastrointestinal upset, metallic taste, bone marrow suppression, rash, pruritus, induction of autoimmune diseases and drug fever.

Arsenic Chelators

• Dimercaprol

Copper Chelators (for Wilson Disease)

• Dimercaprol
• Penicillamine
• Trientine
• Zinc

Iron Chelators

• Deferasirox
• Deferiprone
• Deferoxamine

Lead Chelators

• Dimercaprol
• EDTA
• Succimer

Mercury Chelators

• Dimercaprol

antirheumatic agents

• gold preparations
  • auranofin, gold salts, gold sodium thiomalate

• interleukin receptor antagonists
  • anakinra, canakinumab, rilonacept, sarilumab, tocilizumab

• major immunosuppressive agents (also used in transplant medicine)
  • cyclosporine, mycophenylate, sirolimus, tacrolimus

• monoclonal antibodies
  • adalimumab, canakinumab, certolizumab, golimumab, infliximab, rituximab, sarilumab, tocilizumab, ustekinumab

• thiopurines
  • azathioprine, mercaptopurine, thioguanine

• tumor necrosis factor antagonists
  • adalimumab, certolizumab, etanercept, golimumab, infliximab

• tyrosine (janus) kinase inhibitors
  • baricitinib, tofacitinib

• miscellaneous
  • abatacept, flavocoxid, hydroxychloroquine, leflunomide, methotrexate, penicillamine

• Dailymed label info on Penicillamine
• FDA Penicillamine

Penicillamine

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  Chemical structure of Penicillamine

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  3D model of D-Penicillamine

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  Structure of D-Penicillamine

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  Structure of L-Penicillamine