n.
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.]
penicillamine
Dictionary:
pen·i·cil·la·mine (pĕn'ĭ-sĭl'ə-mēn') 
|
n.
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.
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| Drug Info: Penicillamine |
Brand names: Cuprimine®, Depen®
Chemical formula:
- Drug Forms:
- Penicillamine Oral capsule (below)
- Penicillamine Oral tablet
Penicillamine Oral capsule
What is this medicine?
PENICILLAMINE binds with heavy metals and cystine in the body. It is used to treat Wilson's disease and cystinuria. It is also used to treat rheumatoid arthritis.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• anemia or other blood disorders
• kidney disease
• myasthenia gravis
• an unusual or allergic reaction to penicillamine, penicillin, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I use this medicine?
Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take this medicine on an empty stomach, at least 1 hour before or 2 hours after food. Do not take with food. Take this medicine at least one hour apart from milk or other medicines. Take your medicine at regular intervals. Do not take your medicine more often than directed. Do not skip doses or stop your medicine even if you feel better. Skipping doses for even a few days may cause you to have allergic reactions after restarting this medicine. Do not stop taking except on your doctor's advice.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What may interact with this medicine?
Do not take this medicine with any of the following medications:
• medicines for malaria
This medicine may also interact with the following medications:
• certain antacids that contain aluminum, magnesium
• chemotherapy
• gold compounds used for arthritis
• iron tablets
• multi-vitamins with metals, minerals or iron
• oxyphenbutazone, phenylbutazone
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Visit your doctor or health care professional for regular check ups. It may take 2 to 3 months to improve your symptoms. Tell your doctor if your symptoms do not improve or if you get any new symptoms. You will need to have important blood work done while on this medicine.
You may need to be on a special diet while taking this medicine. Check with your doctor. Ask if you need to take extra vitamin B6 or a multi-vitamin while taking this medicine.
If you are taking this medicine to prevent kidney stones you need to drink plenty of water. Drink at least 2 full glasses of water at bedtime and 2 more full glasses of water during the night.
If you are going to have surgery, tell your doctor or health care professional that you are taking this medicine.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
• allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
• black, tarry stools
• breathing problems
• changes in vision
• dark urine
• dizzy, lightheaded
• fever, chills, sore throat
• joint pain
• mouth sores
• numbness, tingling pain
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• swollen or painful glands
• trouble passing urine or change in the amount of urine
• unusual bleeding or bruising
• unusually weak or tired
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
• anxiety, irritation
• changes in taste
• diarrhea
• loss of appetite
• nausea, vomiting
• stomach pain
• wrinkled or loose skin
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
Keep out of the reach of children.
Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep the medicine container closed tightly. Throw away any unused medicine after the expiration date.
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.
| Wikipedia: Penicillamine |
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|
| 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 |
 (what is this?) (verify) |
|
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.
Contents |
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.
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.
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]
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:. PMID 13279157.
- ^ Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:. PMID 12889074.
External links
- Penicillamine (Systemic) - Medlineplus.org
- Penicillamine and Arthritis - Medicinenet.com
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Drug Info. Gold Standard. Copyright © 2008 by Gold Standard. All rights reserved. Read more |
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