penicillamine (cuprimine) Report issue

Small molecule Approved FDA
AACT ChEMBL DrugBank Drug Central Drugs@FDA KEGG MeSH PubChem repoDB

Active Ingredient History

NOW
  • Now
Penicillamine, sold under the trade names of Cuprimine among others, is a medication primarily used for treatment of Wilson's disease, cystinuria and active rheumatoid arthritis. 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.   NCATS

Chemistry

  • SMILES: CC(C)(S)[C@@H](N)C(O)=O
  • InChIKey: VVNCNSJFMMFHPL-VKHMYHEASA-N
  • Mol. Mass: 149.211
  • ALogP: 0.11
  • ChEMBL Molecule:
    penicillamine  
More Chemistry

Pharmacology

  • Mechanism of Action:
  • Multi-specific: Missing data
  • Black Box: Yes
  • Availability: Prescription Only
  • Delivery Methods: Oral
  • Pro Drug: No

Drug Pricing (per unit)

Australia

$0.2917 - $0.3335

United States

$22.6131 - $92.1208
More Pricing Detail

Note: This drug pricing data is preliminary, incomplete, and may contain errors.

Alternative names

3-mercapto-d-valine | cuprenil | cuprimine | cupripen | depamine | depen | dimethylcysteine | distamine | d mercaptovaline | d-mercaptovaline | d penicillamine | d-penicillamine | d-(−)-penicillamine | d-β,β-dimethylcysteine | pendramine | penicillamine | (−)-penicillamine | (s)-2-amino-3-mercapto-3-methylbutanoic acid | (s)-3,3-dimethylcysteine | trolovol

Organizations (33)

Research & Development (15)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Marketing (19)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Indications (9)

Approved Indications (3)


 

Arthritis, Rheumatoid (approved 1970)

Cystinuria (approved 1970)

Hepatolenticular Degeneration (approved 1970)

Experimental Indications - Clinical Trial Phases 1-4 (8)


 

Arteriovenous Fistula (Phase 2)

Arthritis, Rheumatoid (Phase 3)

Brain Neoplasms (Phase 2)

Head and Neck Neoplasms (Phase 2)

Hepatolenticular Degeneration (Phase 3)

Lead Poisoning (Phase 2/Phase 3)

Neoplasms (Phase 2)

Vitamin D Deficiency (Phase 2/Phase 3)

Overview

  • Highest Phase: Phase 3
  • # of Trials: 9
  • # of Trial Organizations: 15

Trials by Phase

Trial Phase Start Date Organizations Indications

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