GtoPdb Ligand ID: 7264

Synonyms: Cuprimine®
penicillamine is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Penicillamine is a chelating agent and an immunosuppressant.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 102.12
Molecular weight 149.05
XLogP -1.88
No. Lipinski's rules broken 0
Canonical SMILES NC(C(S)(C)C)C(=O)O
Isomeric SMILES N[C@H](C(S)(C)C)C(=O)O
InChI InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
No information available.
Summary of Clinical Use
As a chelating agent penacillamine is used to remove copper from tissues (in patients whose copper-transporting ATPase, ATP7B, is non-functional causing Wilson's disease), to treat cystinuria, and to treat lead poisoning. As an immunosuppressant, this drug is used to treat rheumatoid arthritis and chronic active hepatitis.
Mechanism Of Action and Pharmacodynamic Effects
This drug’s molecular mechanism of action (MMOA) as an immunosuppressant has not been fully resolved. See the DrugBank link for further details.
External links