D-Penicillamine

• Catalog No.: Bio-0578
• CAS Number: 52-67-5
• M. F.: C5H11NO2S
• M. W.: 149.21134

SYNONYMS

• IUPAC name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

DATABASE IDS

• CAS Number: 52-67-5

PROPERTIES

• Application(s): Antiinflammatory
• Application(s): Antirheumatic
• Application(s): Chelating agent used in therapy of metal poisoning, and for Wilson's disease, scleroderma and rheumatoid arthritis
• Mechanism of Action: Chelating agent recommended for the removal of excess copper in patients with Wilson's disease.
• Mechanism of Action: From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine.
• Mechanism of Action: Penicillamine also reduces excess cystine excretion in cystinuria.
• Mechanism of Action: This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide,
• Mechanism of Action: a substance that is much more soluble than cystine and is excreted readily.
• Mechanism of Action: Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed.
• Mechanism of Action: The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity.
• Mechanism of Action: Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins.
• Mechanism of Action: Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.

REFERENCES

• ldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 592B; 592C; 592D; 787A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 892B; 1282C, (nmr)
• Sadtler Standard NMR Spectra, 2305, (pmr)
• Ss, O., Annalen, 1948, 559, 92, (synth)
• Ruiz-Torres, Arzneim.-Forsch., 1974, 24, 914, (pharmacol, metab)
• Rosenfield, R.E. et al., Acta Cryst. B, 1975, 31, 462, (cryst struct, abs config)
• Weigert, W.M. et al., Angew. Chem., Int. Ed., 1975, 14, 330, (rev)
• Parrett, D., Proc. R. Soc. Med., 1977, 70, 61, (metab)
• Jaffe, I.A., Pharmacol. Biochem. Prop. Drug Subst., 1979, 1, 465, (rev, pharmacol)
• Chiu, C.C. et al., Anal. Profiles Drug Subst., 1981, 10, 601, (rev, synth, prop, tox, pharmacol)
• Parrett, D. et al., J. Rheumatol. Suppl., 1981, 7, 28, (rev)
• Scheinberg, I.H. et al., Wilson's Disease, W.B. Saunders, 1984, 126, (use, pharmacol)
• Busker, E. et al., J. Chromatogr., 1985, 350, 179, (sepn)
• Nether, P. et al., Clin. Pharmacokinet., 1987, 13, 317, (pharmacol)
• Wolf-Heuss, E.M., Methods Enzymol., 1987, 143, 186, (rev, detn)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 346
• Ogawa, T. et al., Chem. Pharm. Bull., 1988, 36, 1957; 1989, 37, 1609, (synth)
• Van der Korst, J.K. et al., Inflammatory Dis. Ther., 1992, 9, 203, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 688
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCR750; PAP500; PAP550