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Chemical Compound Review

penicillamine     2-amino-3-methyl-3-sulfanyl- butanoic acid

Synonyms: CHEMBL13239, ACMC-1AMA8, AG-F-79764, ACMC-20999d, ACMC-209l0v, ...
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Disease relevance of penicillamine


Psychiatry related information on penicillamine


High impact information on penicillamine


Chemical compound and disease context of penicillamine


Biological context of penicillamine

  • Both the copper-chelating and immunological effects of penicillamine are probably important in improving survival [20].
  • Liver histology demonstrated a comparative improvement in cholestasis in patients on penicillamine, but the degree of inflammation, necrosis, and the histological stage of disease remained similar in both groups [21].
  • Although exhalation of mercury vapor was a major route of excretion and urinary mercury rose fivefold with administration of penicillamine, excretion by all routes, estimated for the year after injection, represented only 1% of the dose [22].
  • The most potent analog, D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 where Pen is penicillamine in [D-Phe5, Cys6, Tyr7, D-Trp8, Pen11]somatostatin-(5-12)-octapeptide amide, exhibited high affinity for mu-opiate receptors (IC50 value of [3H]naloxone = 3.5 nM), being 7800 times more potent than somatostatin [23].
  • In this study, exogenous NO produced by adding the NO-generator S-nitroso-N-acetyl penicillamine gave a dose-dependent upregulation of transferrin receptor expression by K562 erythroleukemia cells and increased levels of transferrin receptor mRNA [24].

Anatomical context of penicillamine


Associations of penicillamine with other chemical compounds


Gene context of penicillamine

  • Both S-nitroso-N-acetyl penicillamine and diethylenetriaminelNONOate dose-dependently suppressed [3H]-thymidine incorporation in cultured HPASMC, and induced the expression of p53 and p21 protein [34].
  • Similar to LM, CM of Cav1(-/-) mice showed a reduced responsiveness to the NO donors sodium nitroprusside and S-nitroso-N-acetyl penicillamine [35].
  • Inhibition of the covalent binding reaction of complement component C4 by penicillamine, an anti-rheumatic agent [36].
  • Whilst eNOS/NO appears not to be pivotal to early ischaemic preconditioning, NO can nonetheless mediate protection in both WT and KO hearts, as the NO donor, S-nitroso N-acetyl penicillamine (2 microM), was seen to mimic preconditioning protection [37].
  • Dialysis of the PbCl2-inhibited enzyme against buffer alone or buffer plus DL-penicillamine did not result in restoration of PNMT activity [38].

Analytical, diagnostic and therapeutic context of penicillamine


  1. The efficacy of oral zinc therapy as an alternative to penicillamine for Wilson's disease. Cossack, Z.T. N. Engl. J. Med. (1988) [Pubmed]
  2. HLA-DR antigens and toxic reaction to sodium aurothiomalate and D-penicillamine in patients with rheumatoid arthritis. Wooley, P.H., Griffin, J., Panayi, G.S., Batchelor, J.R., Welsh, K.I., Gibson, T.J. N. Engl. J. Med. (1980) [Pubmed]
  3. Trial of penicillamine in advanced primary biliary cirrhosis. Dickson, E.R., Fleming, T.R., Wiesner, R.H., Baldus, W.P., Fleming, C.R., Ludwig, J., McCall, J.T. N. Engl. J. Med. (1985) [Pubmed]
  4. Penicillamine-induced pemphigus. Zone, J., Ward, J., Boyce, E., Schupbach, C. JAMA (1982) [Pubmed]
  5. Acetylcholine receptor antibodies in penicillamine-induced myasthenia gravis. Bocanegra, T.S., Espinoza, L.R., Vasey, F.B., Germain, B.F., Jaffe, I.A., Penn, A.S. JAMA (1981) [Pubmed]
  6. Role of copper in Indian childhood cirrhosis. Tanner, M.S. Am. J. Clin. Nutr. (1998) [Pubmed]
  7. Penicillamine therapy for schizophreniform psychosis in Wilson's disease. Modai, I., Karp, L., Liberman, U.A., Munitz, H. J. Nerv. Ment. Dis. (1985) [Pubmed]
  8. Wilson's disease, a reversible dementia: case report. Rosselli, M., Lorenzana, P., Rosselli, A., Vergara, I. Journal of clinical and experimental neuropsychology : official journal of the International Neuropsychological Society. (1987) [Pubmed]
  9. Acute and chronic toxic nephropathies. Sanders, M.M., Marshall, A.P. Ann. Clin. Lab. Sci. (1989) [Pubmed]
  10. Penicillamine and hydroxychloroquine in the treatment of severe juvenile rheumatoid arthritis. Results of the U.S.A.-U.S.S.R. double-blind placebo-controlled trial. Brewer, E.J., Giannini, E.H., Kuzmina, N., Alekseev, L. N. Engl. J. Med. (1986) [Pubmed]
  11. Acute lymphoblastic leukemia in a patient receiving penicillamine for Wilson's disease. Gilman, P.A., Holtzman, N.A. JAMA (1982) [Pubmed]
  12. Mercury poisoning from home gold ore processing. Use of penicillamine and dimercaprol. Snodgrass, W., Sullivan, J.B., Rumack, B.H., Hashimoto, C. JAMA (1981) [Pubmed]
  13. Toxicity of penicillamine. Goldman, J.A. JAMA (1979) [Pubmed]
  14. Bronchiolitis and bronchitis in connective tissue disease. A possible relationship to the use of penicillamine. Epler, G.R., Snider, G.L., Gaensler, E.A., Cathcart, E.S., FitzGerald, M.X., Carrington, C.B. JAMA (1979) [Pubmed]
  15. Inhibition of hereditary hepatitis and liver tumor development in Long-Evans cinnamon rats by the copper-chelating agent trientine dihydrochloride. Sone, K., Maeda, M., Wakabayashi, K., Takeichi, N., Mori, M., Sugimura, T., Nagao, M. Hepatology (1996) [Pubmed]
  16. Polymyositis with acute myolysis in a patient with rheumatoid arthritis treated with penicillamine and ampicillin. Ostensen, M., Husby, G., Aarli, J. Arthritis Rheum. (1980) [Pubmed]
  17. Toxicity of D-penicillamine in rheumatoid arthritis. A report of 63 patients including two with aplastic anemia and one with the nephrotic syndrome. Weiss, A.S., Markenson, J.A., Weiss, M.S., Kammerer, W.H. Am. J. Med. (1978) [Pubmed]
  18. Effects of lazaroids and a peroxynitrite scavenger in a cell model of peroxynitrite toxicity. Fici, G.J., Althaus, J.S., VonVoigtlander, P.F. Free Radic. Biol. Med. (1997) [Pubmed]
  19. The copper-chelating agent, trientine, suppresses tumor development and angiogenesis in the murine hepatocellular carcinoma cells. Yoshii, J., Yoshiji, H., Kuriyama, S., Ikenaka, Y., Noguchi, R., Okuda, H., Tsujinoue, H., Nakatani, T., Kishida, H., Nakae, D., Gomez, D.E., De Lorenzo, M.S., Tejera, A.M., Fukui, H. Int. J. Cancer (2001) [Pubmed]
  20. D-penicillamine treatment improves survival in primary biliary cirrhosis. Epstein, O., Jain, S., Lee, R.G., Cook, D.G., Boss, A.M., Scheuer, P.J., Sherlock, S. Lancet (1981) [Pubmed]
  21. A controlled trial of D-penicillamine therapy in primary biliary cirrhosis. Jain, S., Scheuer, P.J., Samourian, S., McGee, J.O. Lancet (1977) [Pubmed]
  22. Intravenous elemental mercury injection: blood levels and excretion of mercury. Ambre, J.J., Welsh, M.J., Svare, C.W. Ann. Intern. Med. (1977) [Pubmed]
  23. Conformationally restricted analogs of somatostatin with high mu-opiate receptor specificity. Pelton, J.T., Gulya, K., Hruby, V.J., Duckles, S.P., Yamamura, H.I. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  24. Effect of nitric oxide on expression of transferrin receptor and ferritin and on cellular iron metabolism in K562 human erythroleukemia cells. Oria, R., Sánchez, L., Houston, T., Hentze, M.W., Liew, F.Y., Brock, J.H. Blood (1995) [Pubmed]
  25. Production of nitric oxide in the synovial membrane of rheumatoid and osteoarthritis patients. McInnes, I.B., Leung, B.P., Field, M., Wei, X.Q., Huang, F.P., Sturrock, R.D., Kinninmonth, A., Weidner, J., Mumford, R., Liew, F.Y. J. Exp. Med. (1996) [Pubmed]
  26. Letter: Effect of penicillamine on peripheral-blood lymphocytes in rheumatoid arthritis. Brandt, L., Svensson, B. Lancet (1975) [Pubmed]
  27. Pancreatic duct cells in rats: secretory studies in response to secretin, cholecystokinin-pancreozymin, and gastrin in vivo. Fölsch, U.R., Creutzfeldt, W. Gastroenterology (1977) [Pubmed]
  28. Requirement of the inducible nitric oxide synthase pathway for IL-1-induced osteoclastic bone resorption. van't Hof, R.J., Armour, K.J., Smith, L.M., Armour, K.E., Wei, X.Q., Liew, F.Y., Ralston, S.H. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  29. Increased intracellular glutathione during penicillamine treatment for rheumatoid arthritis. Munthe, E., Guldal, G., Jellum, E. Lancet (1979) [Pubmed]
  30. Treatment of Wilson's disease with zinc. XVII: treatment during pregnancy. Brewer, G.J., Johnson, V.D., Dick, R.D., Hedera, P., Fink, J.K., Kluin, K.J. Hepatology (2000) [Pubmed]
  31. In vitro rheumatoid factor synthesis in patients taking second-line drugs for rheumatoid arthritis.Independent associations with disease activity. Olsen, N.J., Callahan, L.F., Pincus, T. Arthritis Rheum. (1988) [Pubmed]
  32. Decreased pokeweed mitogen-induced IgM and IgM rheumatoid factor synthesis in rheumatoid arthritis patients treated with gold sodium thiomalate or penicillamine. Olsen, N.J., Jasin, H.E. Arthritis Rheum. (1984) [Pubmed]
  33. Aggregation of alpha-synuclein induced by the Cu,Zn-superoxide dismutase and hydrogen peroxide system. Kim, K.S., Choi, S.Y., Kwon, H.Y., Won, M.H., Kang, T.C., Kang, J.H. Free Radic. Biol. Med. (2002) [Pubmed]
  34. p42/44 Mitogen-activated protein kinase regulated by p53 and nitric oxide in human pulmonary arterial smooth muscle cells. Mizuno, S., Kadowaki, M., Demura, Y., Ameshima, S., Miyamori, I., Ishizaki, T. Am. J. Respir. Cell Mol. Biol. (2004) [Pubmed]
  35. Impact of caveolin-1 knockout on NANC relaxation in circular muscles of the mouse small intestine compared with longitudinal muscles. El-Yazbi, A.F., Cho, W.J., Boddy, G., Schulz, R., Daniel, E.E. Am. J. Physiol. Gastrointest. Liver Physiol. (2006) [Pubmed]
  36. Inhibition of the covalent binding reaction of complement component C4 by penicillamine, an anti-rheumatic agent. Sim, E., Dodds, A.W., Goldin, A. Biochem. J. (1989) [Pubmed]
  37. The contribution of endothelial nitric oxide synthase to early ischaemic preconditioning: the lowering of the preconditioning threshold. An investigation in eNOS knockout mice. Bell, R.M., Yellon, D.M. Cardiovasc. Res. (2001) [Pubmed]
  38. Inhibition by lead of phenylethanolamine-N-methyltransferase. Caspers, M.L. Biochem. Pharmacol. (1982) [Pubmed]
  39. Reduction of immune complexes and immunoglobulins induced by D-penicillamine in primary biliary cirrhosis. Epstein, O., De Villiers, D., Jain, S., Potter, B.J., Thomas, H.C., Sherlock, S. N. Engl. J. Med. (1979) [Pubmed]
  40. Toxicity of penicillamine. A serious limitation to therapy in rheumatoid arthritis. Halverson, P.B., Kozin, F., Bernhard, G.C., Goldman, A.L. JAMA (1978) [Pubmed]
  41. Chronic lymphocytic leukaemia after treatment with penicillamine. Clausen, J.E., Arndal, J.C., Gram, L., Kudahl, S.B. Lancet (1978) [Pubmed]
  42. Efficacy of total lymphoid irradiation in intractable rheumatoid arthritis. A double-blind, randomized trial. Strober, S., Tanay, A., Field, E., Hoppe, R.T., Calin, A., Engleman, E.G., Kotzin, B., Brown, B.W., Kaplan, H.S. Ann. Intern. Med. (1985) [Pubmed]
  43. Value of urinary copper excretion after penicillamine challenge in the diagnosis of Wilson's disease. Martins da Costa, C., Baldwin, D., Portmann, B., Lolin, Y., Mowat, A.P., Mieli-Vergani, G. Hepatology (1992) [Pubmed]
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