Difference between revisions of "Penicillamine"
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| IUPAC_name = (2''S'')-2-amino-3-methyl-3-sulfanyl-butanoic acid | | IUPAC_name = (2''S'')-2-amino-3-methyl-3-sulfanyl-butanoic acid | ||
| image = Penicillamine structure.png | | image = Penicillamine structure.png | ||
| + | | image2 = D-Penicillamine-3D-balls.png | ||
| + | | width2 = 190px | ||
| CASNo_Ref = {{cascite}} | | CASNo_Ref = {{cascite}} | ||
| CAS_number = 52-67-5 | | CAS_number = 52-67-5 | ||
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* 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 [[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. | * 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 has been used to treat [[scleroderma]] | ||
| − | * Penicillamine is the 2nd line treatment for arsenic poisonning, after dimercaprol (BAL) | + | * Penicillamine is the 2nd line treatment for arsenic poisonning, after [[dimercaprol]] (BAL) |
==Adverse effects== | ==Adverse effects== | ||
Adverse effects include: | Adverse effects include: | ||
*[[Membranous glomerulonephritis]] <ref name=Kumar8-5> Table 14-2 in: {{cite book |author=Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson |title=Robbins Basic Pathology|publisher=Saunders |location=Philadelphia |year= |pages= |isbn=1-4160-2973-7 |oclc= |doi=}} 8th edition. </ref> | *[[Membranous glomerulonephritis]] <ref name=Kumar8-5> Table 14-2 in: {{cite book |author=Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson |title=Robbins Basic Pathology|publisher=Saunders |location=Philadelphia |year= |pages= |isbn=1-4160-2973-7 |oclc= |doi=}} 8th edition. </ref> | ||
| + | *Aplastic-anemia (idiosyncratic) <ref>Robbins and Cotran, Pathological Basis of Disease 8th Edition, Kumar et al</ref> | ||
*Antibody-mediated [[Lambert-Eaton_myasthenic_syndrome|myasthenic syndrome]] which may persist even after its withdrawal. | *Antibody-mediated [[Lambert-Eaton_myasthenic_syndrome|myasthenic syndrome]] which may persist even after its withdrawal. | ||
*Drug-induced systemic lupus erythematosus | *Drug-induced systemic lupus erythematosus | ||
Revision as of 02:22, 5 August 2010
| File:Penicillamine structure.png | |
| 190px | |
| Systematic (IUPAC) name | |
|---|---|
|
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid | |
| Clinical data | |
| Pregnancy category |
|
| Routes of administration | Oral |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | Variable |
| Metabolism | Hepatic |
| Biological half-life | 1 hour |
| Excretion | Renal |
| Identifiers | |
| CAS Number | 52-67-5 |
| ATC code | M01CC01 (WHO) |
| PubChem | CID 5852 |
| DrugBank | APRD01171 |
| Chemical data | |
| Formula | C5H11NO2S |
| Molar mass | 149.212 g/mol[[Script error: No such module "String".]] |
| (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.
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 2nd line treatment for arsenic poisonning, after dimercaprol (BAL)
Adverse effects
Adverse effects include:
- Membranous glomerulonephritis [1]
- Aplastic-anemia (idiosyncratic) [2]
- Antibody-mediated myasthenic syndrome which may persist even after its withdrawal.
- Drug-induced systemic lupus erythematosus
- Elastosis perforans serpiginosa [3]
History
Dr. John Walshe (1956) first described the use of penicillamine in Wilson's disease.[4] 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.[5]
References
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<references />, or <references group="..." />External links
- Penicillamine (Systemic) - Medlineplus.org
- Penicillamine and Arthritis - Medicinenet.com
es:Penicilamina it:Penicillamina ja:D-ペニシラミン pl:Penicylamina pt:Penicilamina ro:Penicilamina
ru:Пеницилламин- ↑ Table 14-2 in: Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson. Robbins Basic Pathology. Philadelphia: Saunders. ISBN 1-4160-2973-7. 8th edition.
- ↑ Robbins and Cotran, Pathological Basis of Disease 8th Edition, Kumar et al
- ↑ Bolognia, Jean; et al. (2007). Dermatology. Philadelphia: Elsevier. ISBN 1416029990.2nd edition.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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- Amino acids
- Chelating agents
- Antirheumatic products
- Thiols
- World Health Organization essential medicines
- 2Fix
- CS1 maint: Multiple names: authors list
- CS1 maint: Explicit use of et al.
