A degradation product of penicillin, C5H11NO2S, that is used as a chelating agent and in the treatment of rheumatoid arthritis, Wilson's disease, and lead poisoning.
[PENICILL(IN) + –AMINE.]
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A degradation product of penicillin, C5H11NO2S, that is used as a chelating agent and in the treatment of rheumatoid arthritis, Wilson's disease, and lead poisoning.
[PENICILL(IN) + –AMINE.]
Brand names: Cuprimine®, Depen®
Penicillamine tablets or capsules
What are penicillamine tablets or capsules?
PENICILLAMINE (Cuprimine®, Depen®) helps to treat Wilson's disease (too much copper in the body); rheumatoid arthritis; and iron, mercury, arsenic, or lead poisoning. It can also help to prevent kidney stones. Generic penicillamine tablets and capsules are not yet available.What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:How should I take this medicine?
Take penicillamine tablets or capsules by mouth. Follow the directions on the prescription label. Swallow the tablets or capsules with a drink of water. Take penicillamine on an empty stomach, at least 1 hour before or 2 hours after food. Do not take your medicine more often than directed. Finish the full course prescribed by your prescriber or health care professional even if the tablets make you feel unwell. Do not stop taking except on your prescriber's advice.What if I miss a dose?
If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double or extra doses.What drug(s) may interact with penicillamine?
aluminum salts, like aluminum hydroxideWhat should I watch for while taking penicillamine?
Visit your prescriber or health care professional at regular intervals to check on your progress. Penicillamine takes some time to work. If you are treating rheumatoid arthritis or Wilson's disease, you may not notice an improvement in your condition for 2 or 3 months. Take your doses regularly and do not stop taking except on your prescriber's advice.What side effects may I notice from taking penicillamine?
Side effects that you should report to your prescriber or health care professional as soon as possible:Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
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Penicillamine
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| Systematic (IUPAC) name | |
| (2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid | |
| Identifiers | |
| CAS number | |
| ATC code | M01 |
| PubChem | |
| DrugBank | |
| 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. |
? |
| 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.
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:
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).
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![]() | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved. Read more | |
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