l-penicillamine

L-Penicillamine is a medication primarily. It is used for the treatment of Wilson's disease. It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, copper poisoning, and lead poisoning.

DL-Penicillamine (3-Sulfanylvaline) is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. DL-Penicillamine is only found in individuals that have used or taken this drug. It is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of DL-penicillamine. DL-Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between DL-penicillamine and cystine, resulting in the formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cysteine and is excreted readily. DL-Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of DL-penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, DL-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, DL-penicillamine in vitro depresses T-cell activity but not B-cell activity.

S-Nitroso-N-acetyl-DL-penicillamine (SNAP) is a stable inhibitor of platelet aggregation and a nitric oxide donor.

N-Acetyl-DL-penicillamine is a chelating agent.1,2,3It inhibits the binding of methyl mercury to isolated human erythrocytes by 50% and removes 50% of methyl mercury ions from methyl mercury-loaded blood cells when used at a concentration of 1 mM.1,2N-Acetyl-DL-penicillamine (3 mmol kg per day, p.o.) reduces the biological half-life of mercury and decreases liver, kidney, brain, and blood mercury levels, as well as increases urinary excretion of mercury in a concentration-dependent manner, in mice when administered following injection of methyl mercuric chloride. It decreases mercuric chloride-induced mortality in mice when administered orally at a dose of 1.6 mmol kg.3N-Acetyl-DL-penicillamine is also an analog of SNAP that does not generate nitric oxide and has been used as a negative control in experiments using SNAP.4,5

L-Histidinyl-D-penicillaminatocobalt(III) can provide a model for the binding of D-penicillamine to metal ions.