|Accession Number||DB00859 (APRD01171)|
Penicillamine is a pharmaceutical of the chelator class. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine). It is an α-amino acid metabolite of penicillin, although it has no antibiotic properties.
|Product Ingredients||Not Available|
|Approved Prescription Products|
|Approved Generic Prescription Products||Not Available|
|Approved Over the Counter Products||Not Available|
|Unapproved/Other Products||Not Available|
|Brand mixtures||Not Available|
|Weight||Average: 149.211 |
For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.
Penicillamine is a chelating agent used in the treatment of Wilson's disease. It is also used to reduce cystine excretion in cystinuria and to treat patients with severe, active rheumatoid arthritis unresponsive to conventional therapy. 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. Its use in Wilson's disease, a rare genetic disorder of copper metabolism, relies on its binding to accumulated copper and elimination through urine.
|Mechanism of action|
Penicillamine is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cystine and is excreted readily. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.
rapidly but incompletely
|Volume of distribution||Not Available|
>80% (bound to plasma proteins)
|Route of elimination|
Excretion is mainly renal, mainly as disulfides.
|Pharmacogenomic Effects/ADRs||Not Available|
Manfred Klaus Joachim Bock, deceased, "Method of producing penicillamine." U.S. Patent US3968154, issued November, 1960.US3968154
|ATC Codes||M01CC01 — Penicillamine|
|AHFS Codes||Not Available|
|PDB Entries||Not Available|
|FDA label||Download (264 KB)|
|MSDS||Download (71.7 KB)|
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|Predicted ADMET features|
|Mass Spec (NIST)||Download (7.76 KB)|
|Description||This compound belongs to the class of chemical entities known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.|
|Super Class||Organic compounds|
|Class||Organic acids and derivatives|
|Sub Class||Carboxylic acids and derivatives|
|Direct Parent||Valine and derivatives|
|Alternative Parents||D-alpha-amino acids / Thia fatty acids / Methyl-branched fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds|
|Substituents||Valine or derivatives / Alpha-amino acid / D-alpha-amino acid / Branched fatty acid / Methyl-branched fatty acid / Thia fatty acid / Fatty acyl / Fatty acid / Amino acid / Alkylthiol/ Carboxylic acid / Monocarboxylic acid or derivatives / Organic nitrogen compound / Primary amine / Organosulfur compound / Organooxygen compound / Organonitrogen compound / Hydrocarbon derivative / Primary aliphatic amine / Organic oxide / Carbonyl group / Organopnictogen compound / Amine / Organic oxygen compound / Aliphatic acyclic compound|
|Molecular Framework||Aliphatic acyclic compounds|
|External Descriptors||penicillamine (CHEBI:7959 )|
- Pharmacological action
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- Uniprot ID:
- Uniprot Name:
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight:
- 76447.99 Da
- Gui C, Hagenbuch B: Role of transmembrane domain 10 for the function of organic anion transporting polypeptide 1B1. Protein Sci. 2009 Nov;18(11):2298-306. doi: 10.1002/pro.240. [PubMed:19760661 ]