Toxicology and safety of comt inhibitors

International Review of Neurobiology

Volumn 95, Issue C, 2010, Pages 163-189

  Haasio, Kristiina ^a  

^a ORION CORPORATION   (Finland)

Author keywords

COMT inhibition; Entacapone; Nebicapone; Safety; Tolcapone; Toxicity

Indexed keywords

2,5 DICHLORO 3 [5 (3,4 DIHYDROXY 5 NITROPHENYL) 1,2,4 OXADIAZOL 3 YL] 4,6 DIMETHYLPYRIDINE 1 OXIDE; 3',4' DIHYDROXY 2 METHYLPROPIOPHENONE; BIA 3 335; BIA 9 1067; CATECHOL; CATECHOL METHYLTRANSFERASE INHIBITOR; ENTACAPONE; ENZYME INHIBITOR; GALLIC ACID BUTYL ESTER; GALLIC ACID DERIVATIVE; LEVODOPA; METHYLTRANSFERASE INHIBITOR; N (6 OXO 1H PYRID 2 YL) N',N' DIPROPYLFORMAMIDINE; NEBICAPONE; NITECAPONE; PLACEBO; PYROGALLOL; TOLCAPONE; TRANSFERASE INHIBITOR; TROPOLONE; UNCLASSIFIED DRUG;

ABDOMINAL PAIN; ALANINE AMINOTRANSFERASE BLOOD LEVEL; AMINOTRANSFERASE BLOOD LEVEL; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; BEHAVIOR DISORDER; BOOK; CLINICAL TRIAL; CONSTIPATION; CONVULSION; DIARRHEA; DOSE RESPONSE; DRUG DOSE INCREASE; DRUG DOSE REDUCTION; DRUG MECHANISM; DRUG MEGADOSE; DRUG PENETRATION; DRUG PROTEIN BINDING; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG USE; DRUG WITHDRAWAL; DYSKINESIA; ENZYME INHIBITION; FATIGUE; GASTROINTESTINAL SYMPTOM; HALLUCINATION; HEADACHE; HUMAN; INSOMNIA; LD 50; LIVER TOXICITY; METHEMOGLOBINEMIA; MITOCHONDRIAL MEMBRANE POTENTIAL; MUSCLE CRAMP; NAUSEA; NEPHRITIS; NEUTROPHIL; NONHUMAN; ORTHOSTATIC HYPOTENSION; OXIDATIVE STRESS; PARKINSON DISEASE; PARKINSONISM; PRIORITY JOURNAL; SCHIZOPHRENIA; SEDATION; SIDE EFFECT; SOMNOLENCE; SWEATING; TACHYCARDIA; THROMBOCYTE DISORDER; VOMITING;

EID: 78649353389     PISSN: 00747742     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-381326-8.00007-7     Document Type: Chapter

References (126)

1. Aboud G., Kaplowitz N. Drug-Induced liver injury. Drug Saf. 2007, 30:277-294.
2. Acuna G., Foernzler D., Leong D., Gasser R., Dorflinger E., Borroni E., To Z., Smit R., Rabbia M., Thompson A., Hashimoto L., Lindpaintner K. Genetic susceptibility to tolcapone-induced liver injury. Parkinsonism. Relat. Disord. 2001, 7(Suppl.):S25.
3. Acuna G., Foernzler D., Leong D., Rabbia M., Smit R., Dorflinger E., Gasser R., Hoh J., Ott J., Borroni E., To Z., Thompson A., Li J., Hashimoto L., Lindpaintner K. Pharmacogenetic analysis of adverse drug effect reveals genetic variant for susceptibility to liver toxicity. Pharmacogenomics J. 2002, 2:327-334.
4. Almeida L., Loureiro A.I., Vaz-da-Silva M., Torrao L., Maia J., Fernandes-Lopes C., Falcao A., Igreja B., Wright L., Soares-da-Silva P. Chronopharmacology of nebicapone, a new catechol-O-methyltransferase inhibitor. Curr. Med. Res. Opin. 2010, 26:1097-1108.
5. Angel A., Rodgers K.J. Convulsant action of polyphenols. Nature 1968, 217:84-85.
6. Angrist B., Park S., Urcuyo L., Roffman M., Gershon S. Clinical evaluation of a possible catechol-O-methyltransferase inhibitor in endogenous depression. Curr. Ther. Res. 1973, 15:127-132.
7. Assal F., Spahr L., Hadengue A., Rubbici-Brandt L., Burkhard P. Tolcapone and fulminant hepatitis. Lancet 1998, 352:958.
8. Axelrod J., LaRoche M.-J. Inhibitor of O-methylation of epinephrine and norepinephrine in vitro and in vivo. Science 1959, 130:800-801.
9. Axelrod J., Tomchick R. Enzymatic O-methylation of epinephrine and other catechols. J. Biol. Chem. 1958, 233:702-705.
10. Baas H., Beiske A.G., Ghika J., Jackson M., Oertel W.H., Poewe W., Ransmayr G. Catechol-O-methyltransferase inhibition with tolcapone reduces the "wearing off" phenomenon and levodopa requirements in fluctuating parkinsonian patients. J. Neurol. Neurosurg. Psychiatr. 1997, 63:421-428. and the study investigators.
11. Bakke O.M. O-methylation of simple phenols in the rat. Acta Pharmacol. Toxicol. 1970, 28:28-38.
12. Baldessarini R.J., Greiner E. Inhibition of catechol-O-methyl transferase by catechols and polyphenols. Biochem. Pharmacol. 1973, 22:247-256.
13. Beck S., Hubble J., Reinikainen K. Entacapone-induced hepatotoxicity and hepatic dysfunction. Mov. Disord. 2002, 17:1397-1399.
14. Belleau B., Burba J. Tropolones: a unique class of potent non-competitive inhibitors of S-adenosylmethionine-catechol methyltransferase by tropolones. Biophys. Acta 1961, 54:195-196.
15. Belleau B., Burba J. Occupancy of adrenergic receptors and inhibition of catechol-O-methyl-transferase by tropolones. J. Med. Chem. 1963, 6:755-759.
16. Berg J.M., Tymoczko L., Stryer L. Oxidative phosphorylation. Biochemistry 2002, 491-523. W.H. Freeman and Company, New York. 5th ed.
17. Bertollini F., Novaroli L., Carrupt P.-A., Reist M. Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function. J. Pharm. Sci. 2007, 96:2931-2944.
18. Bonifacio M.J., Archer M., Rodrigues M.L., Matias P.M., Learmonth D.A., Carrondo M.A., Soares-da-Silva P. Kinetics and crystal structure of catechol-O-methyltransferase complex with co-substrate and a novel inhibitor with potential therapeutic application. Mol. Pharmacol. 2002, 62:795-805.
19. Bonifacio M.J., Torrao L., Wright L., Soares-da-Silva P. Membrane-bound COMT inhibition by nebicapone. FASEB J. 2007, 21(804):3.
20. Bonifacio M.J., Vieira-Coelho M.A., Soares-da-Silva P. Kinetic inhibitory profile of BIA 3-202, a novel fast tight-binding, reversible and competitive catechol-O-methyltransferase inhibitor. Eur. J. Pharmacol. 2003, 460:163-170.
21. Bonifati V., Meco G. New, selective catechol-O-methyltransferase inhibitors as therapeutic agents in Parkinson's disease. Pharmacol. Ther. 1999, 81:1-36.
22. Borgulya J., Da Prada M., Dingemanse J., Scherschlicht R., Schläppi B., Zürcher G. Ro 40-7592. Catechol-O-methyltransferase (COMT) inhibitor. Drugs Future 1991, 16:719-721.
23. Borgylua J., Bryderer H., Bernauer K., Zürcher G., Da Prada M. Catechol-O-methyltransferase-inhibiting pyrocatechol derivativesmdash;synthesis and structure activity studies. Helv. Chim. Acta 1989, 72:952-968.
24. Borroni E., Beck J., Cesura A.M., Schmitt M., Gatti S. Tolcapone and mitochondrial function: evidence for a large safety margin in vitro and in vivo. Parkinson. Relat. Disord. 1999, 5:S68.
25. Borroni E., Cesura A.M., Gatti S., Gasser R. A preclinical re-evaluation of the safety profile of tolcapone. Funct. Neurol. 2001, 16(Suppl.):125-134.
26. Broch O.J.J. The in vivo effect of tropolone on dopamine metabolism and the catechol-O-methyl transferase activity in the striatum of the rat. Acta Pharmacol. Toxicol. 1972, 31:217-225.
27. Brooks D.J. Optimizing levodopa therapy for Parkinson's disease with levodopa/carbidopa/entacapone: implications from a clinical and patient perspective. Neuropsychiatr. Dis. Treat. 2008, 4:39-47.
28. Brooks D.J., Sagar H. Entacapone is beneficial in both fluctuating and non-fluctuating patients with Parkinson's disease: a randomised, placebo controlled, double-blind, six month study. J. Neurol. Neurosurg. Psychiatr. 2003, 74:1071-1079. The UK-Irish Entacapone Study Group.
29. Bäckström R., Honkanen E., Pippuri A., Kairisalo P., Pystynen J., Heinola K., Nissinen E., Linden I.-B., Männist P., Kaakkola S., Pohto P. Synthesis of some novel potent and selective catechol O-methyltransferase inhibitors. J. Med. Chem. 1989, 32:841-846.
30. Brown G.C. Control of respiration and ATP synthesis in mammalian mitochondria and cells. Biochem. J. 1992, 284:1-13.
31. Colossimo C. The rise and fall of tolcapone. J. Neurol. 1999, 246:880-882.
32. Conyers R.A.J., Hensley W.J., Montague M.D. The effect of pyrogallol on oxidative phosphorylation. Arch. Int. Pharmacodyn. 1968, 171:179-184.
33. Dingemanse J. Catechol-O-methyltransferase inhibitors: clinical potential in the treatment of Parkinson's disease. Drug R. D. 1997, 42:1-25.
34. Dingemanse J., Jorga K., Zürcher G., Schmitt M., Sedek G., Da Prada M., Van Brummelen P. Pharmacokinetic-pharmacodynamic interaction between the COMT inhibitor tolcapone and single-dose levodopa. Br. J. Pharmacol. 1995, 40:253-262.
35. Dorris R.L., Dill R.E. Inhibition of catechol-O-methyltransferase by N-butyl gallate. Neuropharmacology 1977, 16:631-634.
36. Dossing M., Sonne J. Drug-induced hepatic disorders. Drug Saf. 1993, 9:441-449.
37. Eckhardt K., Fukatsu N., Hayashi M., Horii I. Embryotoxicicity study in rats with oral administration of tolcapone. Jpn. Pharmacol. Ther. 1996, 24:123-139.
38. Comtess, entacapone-A COMT inhibitor for treatment of Parkinson's Disease. A Product Monograph 1999, Entacapone Product Monograph, Orion-Adis International Ltd.
39. Ericsson A.D. Potentiation of the L-dopa effect in man by the use of catechol-O-methyltransferase inhibitors. J. Neurol. Sci 1971, 14:193-197.
40. Recommendation for the suspension of the marketing authorisation for Tasmar (tolcapone) 1998, European Medicine Evaluation Agency, Press Release, London.
41. EPARs for authorised medicinal products for human use, Tasmar. host European Medicines Agency. http://www.ema.europa.eu.
42. Fahn S., Comi R., Snider R.S., Prasad A.L.N. Effect of a catechol-O-methyl transferase inhibitor, U-0521, with levodopa administration. Biochem. Pharmacol. 1979, 28:1221-1225.
43. Ferreira J.J., Almeida L., Cunha L., Ticmeanu M., Rosa M.M., Januario C., Mitu C.-E., Coelho M., Correia-Guedes L., Morgadinho A., Nunes T., Wright L.C., Falcao A., Sampaio C., Soares-da-Silva P. Effects of nebicapone on levodopa pharmacokinetics, catechol-O-methyltransferase activity, and motor fluctuation in patients with Parkinson disease. Clin. Neuropharmacol. 2008, 31:2-18.
44. Ferreira J.J., Rascol O., Poewe W., Sampaio C., Rocah F., Nunes T., Almeida L., Soares-da-Silva P. A double-blind, randomized, placebo-controlled trial to investigate the efficacy and safety of nebicapone in levodopa-treated Parkinson's disease patients with motror fluctuations. Mov. Disord. 2008, 23(Suppl. 1):S195. Nebicapone 202 Study Group.
45. Fischer J., Michaelis S., Schrey A.K., Baessler O., Glinski M., Dreger M., Krolla F., Koester H. Capture compound mass spectrometry sheds light on the molecular mechanisms of liver toxicity of two Parkinson drugs. Toxicol. Sci. 2010, 113:243-253.
46. Fisher A., Croft-Baker J., Davis M., Purcell P., McLean A. Entacapone-induced hepatotoxicity and hepatic dysfunction. Mov. Disord. 2002, 17:1362-1365.
47. Forsberg M.M., Juvonen R.O., Helisalmi P., Leppänen J., Gogos J.A., Karayiorgou M., Männist P.T. Lack of increased oxidative stress in catechol-O-methyltransferase COMT)-deficient mice. Naunyn-Schmiedeberg's Arch. Pharmacol. 2004, 370:279-289.
48. Gasser R., Smit R. Predictor analysis of liver enzyme abnormalities in association with Tasmar® (tolcapone) treatment. Parkinson. Relat. Disord. 2001, 7(Suppl.):S57.
49. Gogos J.A., Morgan M., Luine V., Santha M., Ogawa S., Pfaff D., Karayiorgou M. Catechol-O-methyltransferase-deficient mice exhibit sexually dimorphic changes in catecholamine levels and behaviour. Proc. Natl. Acad. Sci. 1998, 95:9991-9996.
50. Grossman M., Creveling C., Rybczynski R., Braverman M., Isersky C., Breaefiel X. Soluble and particulate forms of rat catechol-O-methyltransferase distinguished by gel electrophoresis and immune fixation. J. Neurochem. 1985, 44:421-432.
51. Gugler R., Dengler H.J. Inhibition of human liver catechol-O-methyltransferase by flavonoids. Naunyn Schmiedebergs Arch. Pharmacol. Exp. Pathol. 1973, 276:223-233.
52. Guldberg H., Marsden C. Catechol-O-methyl transferase: pharmacological aspects and physiological role. Pharmacol. Rev. 1975, 27:135-206.
53. Haasio K., Huotari M., Nissinen E., Männist P.T. Tissue histopathology, clinical chemistry and behaviour of adult Comt-gene disrupted mice. J. Appl. Toxicol. 2003, 23:213-219.
54. Haasio K., Koponen A., Penttil K.E., Nissinen E. Effects of entacapone and tolcapone on mitochondrial membrane potential. Eur. J. Pharm. 2002, 453:21-26.
55. Haasio K., Lounatmaa K., Sukura A. Entacapone does not induce conformational changes in liver mitochondria or skeletal muscle in vivo. Exp. Toxic. Pathol. 2002, 54:9-14.
56. Haasio K., Nissinen E., Sopanen L., Heinonen E.H. Different toxicological profile of two COMT inhibitors in vivo: the role of uncoupling effects. J. Neural. Transm. 2002, 109:1391-1401.
57. Haasio K., Sopanen L., Vaalavirta L., Lindén I.-B., Heinonen E.H. Comparative toxicological study on the hepatic safety of entacapone and tolcapone in the rat. J. Neural. Transm. 2001, 108:79-91.
58. Hirakawa B., Twamley M., Lu B., Lawton M., Younis H.S. Hepatic toxicogenomic profiling in rats as a predictor of idiosyncratic drug-induced liver injury in humans. Toxicol. Sci. 2008, 102(Suppl.):324.
59. Horner W. Dinitrophenol and its relation to formation of cataract. Arch. Ophthalmol. 1942, 27:1097-1121.
60. Huotari M., Gogos J., Karayiorgou M., Koponen O., Forsberg M., Raasmaja A., Hyttinen J., Männist P.T. Brain catecholamine metabolism in catechol-O-methyltransferase (COMT)-deficient mice. Eur. J. Neurosci. 2002, 15:246-256.
61. Inamori Y., Tsujibo H., Ohishi H., Ishii F., Mizugaki M., Aso H., Ishida N. Cytotoxic effect of hinokitiol and tropolone on the growth of mammalian cells and on blastogenesis of mouse splenic T cells. Biol. Pharm. Bull. 1993, 16:521-523.
62. Kaakkola S. Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson's disease. Drugs 2000, 59:1233-1250.
63. Kaakkola S., Gordin A., Männist P.T. General properties and clinical possibilities of new selective inhibitors of catechol-O-methyltransferase. Gen. Pharmacol. 1994, 25:813-824.
64. Kaplowitz N. Causality assessment versus guilt-by-association in drug hepatotoxicity. Hepatology 2001, 33:308-310.
65. Kaplowitz N. Idiosyncratic drug hepatotoxicity. Nat. Rev. 2005, 4:489-499.
66. Karhunen T., Tilgmann C., Ulmanen I., Julkunen I., Panula P. Distribution of catechol-O-methyltransferase enzyme in rat tissues. J. Histochem. Cytochem. 1994, 42:1079-1090.
67. Keränen T., Gordin A., Karlsson M., Korpela K., Pentikäinen P.J., Rita H., Schultzt E., Seppäl E., Wikberg T. Inhibition of soluble catechol-O-methyltransferase and single-dose pharmacokinetics after oral and intravenous administration of entacapone. Eur. J. Clin. Pharmacol. 1994, 46:151-157.
68. Kiss L.E., Ferreira H.S., Torrao L., Bonifacio M.J., Palma P.N., Soares-da-Silva P., Learmonth D.A. Discovery of a long-acting, peripherally selective inhibitor of catechol-O-methyltransferase. J.Med.Chem. 2010, 53:3396-3411.
69. Korlipara L.V.P., Cooper J.M., Schapira A. Differences in toxicity of the catechol-O-methyl transferase inhibitors, tolcapone and entacapone to cultured human neuroblastoma cells. Neuropharmacology 2004, 46:562-569.
70. Kurth M.C., Adler C.H., Hilaire M.S., Singer C., Waters C., LeWitt P., Chernik D.A., Dorflinger E.E., Yoo K. Tolcapone improves motor function and reduces levodopa requirement in patients with Parkinson's disease experiencing motor fluctuations: a multicenter, double-blind, randomized, placebo-controlled trial. Tolcapone Fluctuator Study Group I. Neurology 1997, 48:81-87.
71. Leegwater-Kim J., Waters C. Role of tolcapone in the treatment of Parkinson's disease. Expert Rev. Neurother 2007, 7:1649-1657.
72. Lees A.J., Ratziu V., Tolosa E., Oertel W.H. Safety and tolerability of adjunctive tolcapone therapy in early Parkinson's disease patients. J. Neurol. Neurosurg. Psychiatry 2007, 78:944-948.
73. Lotta T., Vidgren J., Tilgmann C., Ulmanen I., Melén K., Julkunen I., Taskinen J. Kinetics on human soluble and membrane-bound catechol-O-methyltransferase: a revised mechanism and description of the thermolabile variant of the enzyme. Biochemistry 1995, 34:4202-4210.
74. Loureiro A.I., Bonifacio M.J., Fernandes-Lopes C., Almeida L., Wright L.C., Soares-da-Silva P. Human metabolism of nebicapone (BIA 3-202), a novel catechol-O-methyltransferase inhibitor: characterization of in vitro glucuronidation. Drug Metab. Dispos. 2006, 34:1856-1862.
75. Maitre L. Effects of long-term administration of pyrogallol on tissue catecholamine levels, monoamine oxidase and catechol-O-methyltransferase activites in the rat. Biochem. Pharmacol. 1966, 15:1935-1946.
76. Männist P.T., Kaakkola S. Catechol-O-methyltransferase (COMT): biochemistry, molecular biology, pharmacology, and clinical efficacy of the new selective COMT inhibitors. Pharmacol. Rev. 1999, 51:593-628.
77. Männistö P.T., Tuomainen P., Tuominen R.K. Different in vivo properties of three new inhibitors of catechol-O-methyltransferase in the rat. Br. J. Pharmacol. 1992, 105:569-574.
78. Marcocci L., Maguire J.J., Packer L. Nitecapone: a nitric oxide radical scavenger. Biochem. Mol. Biol. Int. 1994, 34:531-541.
79. Mayoral W., Lewis J.H., Zimmerman H. Drug-induced liver disease. Curr. Opin. Gastroenterol. 1999, 15:208-216.
80. McBurney R.N., Hines W.M., vonTungeln L.S., Schnackenberg L.K., Beger R.D., Moland C.L., Han T., Fuscoe J.C., Chang C.-W., Chen J.J., Su Z., Fan X.-H., Tong W., Booth S.A., Balasubramanian R., Courchesne P.L., Campbell J.M., Graber A., Guo Y., Juhaz P.J., Li T.Y., Lynch M.D., Morel N.M., Plasterer T.N., Takach E.J., Zeng C., Beland F.A. The liver toxicity biomarker study: phase I design and preliminary results. Toxicol. Pathol. 2009, 37:52-64.
81. McCaul T.F., Fagan E.A., Tovey G., Portman B., Williams R., Zuckerman A.J. Fulminant hepatitis. An ultrastructural study. J. Hepatol. 1986, 2:276-290.
82. Myllylä V.V., Kultalahti E.R., Haapaniemi H., Leinonen M. Twelve-month safety of entacapone in patients with Parkinson's disease. Eur. J. Neurol. 2001, 8:53-60. FILOMEN Study Group.
83. Myöhänen T.T., Schendzielorz N., Männist P.T. Distribution of catechol-O-methyltransferase (COMT) proteins and enzymatic activities in wild-type and soluble COMT deficient mice. J. Neurochem. 2010, 113:1632-1643.
84. Nakagawa Y., Tayama K. Mechanism of mitochondrial dysfunction and cytotoxicity induced by tropolones in isolated rat hepatocytes. Chem. Biol. Interact. 1998, 116:45-60.
85. Nakagawa Y., Tayama S. Cytotoxicity of propylgallate and related compounds in rat hepatocytes. Arch. Toxicol. 1995, 69:204-208.
86. Nissinen E., Kaheinen P., Penttil K., Kaivola J., Lindén I.-B. Entacapone, a novel catechol-O-methyl transferase inhibitor of Parkinson's disease, does not impair mitochondrial energy production. Eur. J. Pharmacol. 1997, 340:287-294.
87. Nissinen E., Lindén I.-B., Schultz E., Pohto P. Biochemical and pharmacological properties of a peripherally acting catechol-O-methytransferase inhibitor Entacapone. Naunyn Schmiedebergs Arch. Pharmacol. 1992, 346:262-266.
88. Nissinen E., Tuominen R., Perhoniemi V., Kaakkola S. Catechol-O-methyltransferase activity in human and rat small intestine. Life Sci. 1988, 42:2609-2614.
89. Olanow C.W. Tolcapone and hepatotoxic effects. Arch. Neurol. 2000, 57:263-267. Tasmar Advisory Panel.
90. Orth M., Schapira A.H.V. Mitochondrial involvement in Parkinson's disease. Neurochem. Int. 2002, 40:533-541.
91. Parada A., Loureiro A.I., Vieira-Coelho M.A., Hainzl D., Soares-da-Silva P. BIA 3-202, a novel catechol-O-methyltransferase inhibitor, enhances the availability of L-DOPA to the brain and reduces its O-methylation. Eur. J. Pharm. 2001, 420:27-32.
92. Pedrosa R., Soares-da-Silva P. Oxidative and non-oxidative mechanisms of neuronal cell death and apoptosis by L-3,4-dihydroxyphenylalanine (L-Dopa) and dopamine. Br. J. Pharmacol. 2002, 137:1305-1313.
93. Poewe W.H., Deuschl G., Gordin A., Kultalahti E.R., Leinonen M. Efficacy and safety of entacapone in Parkinson's disease patients with suboptimal levodopa response: a 6-month randomized placebo-controlled double-blind study in Germany and Austria (Celomen study). Acta Neurol. Scand. 2002, 105:245-255. Celomen Study Group.
94. Rajput A.H., Martin W., Saint-Hilaire M.-H., Dorflinger E., Pedder S. Tolcapone improves motor function in parkinsonian patients with the "wearing-off" phenomenon: a double-blind, placebo-controlled, multicenter trial. Neurology 1997, 49:1066-1071.
95. Reches A., Fahn S. Catechol-O-methyltransferase and Parkinson's disease. Adv. Neurol. 1984, 40:171-179.
96. Ri S. Pharmacological studies of hinokitiol. I. On the toxicity and the local action of hinokitiol. Niigata Igakkai Zasshi 1951, 65:566-572.
97. Rinne U.K., Larsen J.P., Siden A., Worm-Petersen J. Entacapone enhances the response to levodopa in parkinsonian patients with motor fluctuations. Neurology 1998, 51:1309-1314. Nomecomt Study Group.
98. Ross S.B., Haljasmaa Ö Catechol-O-methyl transferase inhibitors. In vitro inhibition of the enzyme in mouse-brain extract. Acta Pharmacol. Toxicol. 1964, 21:205-214.
99. Ross S.B., Haljasmaa Ö Catechol-O-methyl transferase inhibitors. In vivo inhibition in mice. Acta Pharmacol. Toxicol. 1964, 21:215-225.
100. Schapira A.H.V. Evidence for mitochondrial dysfunction in Parkinson's disease-a critical appraisal. Mov. Disord. 1994, 9:125-138.
101. Schapira A.H.V. Causes of neuronal death in Parkinson's disease. Adv. Neurol. 2001, 86:155-161.
102. Schläppi B., Jovanovic D., Okada M., Kobayashi K., Horii I. Six-month oral toxicity study of tolcapone in rats (feed admix). Jpn. Pharmacol. Ther. 1996, 24:49-102.
103. Schläppi B., Morimoto H., Kobayashi K., Horii I. Six-month oral toxicity study with tolcapone on Beagle dogs. Jpn. Pharmacol. Ther. 1996, 24(Suppl. 10):77-102.
104. Schläppi B., Okada M., Kobayashi K., Horii I. Four-week oral toxicity study of tolcapone in rats (gavage). Jpn. Pharmacol. Ther. 1996, 24:13-27.
105. Simpson G.M., Varga V. An investigation of the clinical effect of GPA-1714, a catechol-O-methyl transferase inhibitor. J. Clin. Pharmacol. New Drugs 1972, 10:417-421.
106. Smith K.S., Smith P.L., Heady T.N., Trugman J.M., Harman W.D., Macdonald T.L. In vitro metabolism of tolcapone to reactive intermediates: relevance to tolcapone liver toxicity. Chem. Res. Toxicol. 2003, 16:123-128.
107. Spahr L., Rubbia-Brandt L., Burkhard P., Assal F., Hadengue A. Tolcapone-related fulminant hepatitis: electron microscopy shows mitochondrial alterations. Dig. Dis. Sci. 2000, 45:1881-1884.
108. Sun J., vonTungeln L.S., Hines W., Beger R.D. Identification of metabolite profiles of the catechol-O-methyl transferase inhibitor tolcapone in rat urine using LC/MS-based metabonomic analysis. J. Chromatogr. 2009, B 877:2557-2565.
109. Suzuki Y.J., Tsuchiya M., Safadi A., Kagan V.E., Packer L. Antioxidant properties of nitecapone (OR-462). Free Rad. Biol. Med. 1992, 13:517-525.
110. Tafazoli S., Soehar D.D., O'Brien P.J. Oxidative stress mediated idiosyncratic drug toxicity. Drug Metab. Rev. 2005, 37:311-325.
111. 1997, Tasmar Product Monograph, Roche Pharmaceuticals, Basel, Switzerland.
112. Tenhunen J., Salminen M., Lundström K., Kiviluoto T., Savolainen R., Ulmanen I. Genomic organization of the human catechol O-methyltransferase gene and its expression from two distinct promoters. Eur. J. Pharm. 1994, 223:1049-1059.
113. Terada H. Uncouplers of oxidative phosphorylation. Environ. Health Perspect. 1990, 87:213-218.
114. Tilgmann C., Melen K., Lundström K., Jalanko A., Julkunen I., Kalkkinen N., Ulmanen I. Expression of recombinant soluble and membrane-bound catechol-O-methyltransferase in eukaryotic cells and identification of the respective enzymes in rat brain. Eur. J. Biochem. 1992, 207:813-821.
115. Törnwall M., Männist P.T. Acute toxicity of three new selective COMT inhibitors in mice with special emphasis on interactions with drug increasing catecholaminergic neurotransmission. Pharmacol. Toxicol. 1991, 69:64-70.
116. Ulmanen I., Peränen J., Tenhunen J., Tilgmann C., Karhunen T., Panula P., Bernasconi L., Aubry J.-P., Lundström K. Expression and intracellular localization of catechol O-methyltransferase in transfected mammalian cells. Eur. J. Biochem. 1997, 243:452-459.
117. Unger M.M., Reese J.P., Oertel W.H., Eggert K.M. Real-life evaluations of compliance with mandatory drug safety monitoring exemplified with tolcapone in Parkinson's disease. Eur. Neurol. 2008, 60:122-126.
118. Vieira-Coelho M.A., Soares-da-Silva P. Effects of tolcapone upon soluble and membrane-bound brain and liver catechol-O-methyltransferase. Brain Res. 1999, 821:69-78.
119. Waldmeier P.C., Baumann P.A., Feldtrauer J.J., Hauser K., Bittiger H., Bischoff S., Von Sprecher G. CGP 28014, a new inhibitor of cerebral catechol-O-methylation with a non-catechol structure. Naunyn Schmiedebergs Arch. Pharmacol. 1990, 342:305-311.
120. Waters C.H., Kurth M., Bailey P., Shulman L.M., LeWitt P., Dorflinger E., Deptula D., Pedder S. Tolcapone in stable Parkinson's disease: efficacy and safety of long-term treatment. Neurology 1997, 49:665-671. The Tolcapone Stable Study Group.
121. Watkins P. COMT inhibitors and liver toxicity. Neurology 2000, 55(Suppl. 4):S51-S52.
122. Wikberg T., Vuorela A., Ottoila P., Taskinen J. Identification of major metabolites of the catechol-O-methyltransferase inhibitor entacapone in rats and humans. Drug Metab. Dispos. 1993, 21:81-92.
123. Wright L.C., Maia J., Loureiro A.I., Almeida L., Soares-da-Silva P. Pharmacokinetics, disposition and metabolism of [14C]-Nebicapone in humans. Drug Metabol. Lett. 2010, 4:149-162.
124. Wylie D.W., Archer S., Arnold A. Augmentation of pharmacological properties of catecholamines by O-methyl transferase inhibitors. J. Pharmacol. Exp. Ther. 1960, 130:239-244.
125. Zürcher G., Colzi A., Da Prada M. Ro 40-7592-Inhibition of COMT in rat brain and extracerebral tissues. J. Neural. Transm. 1990, 32(Suppl.):375-380.
126. Zürcher G., Keller H.H., Kettler R., Borgylua J., Bonetti E.P., Eigenmann R., Da Prada M. Ro 40-7592, a novel, very potent, and orally active inhibitor of catechol-O-methyltransferase: a pharmacological study in rats. Adv. Neurol. 1990, 53:497-503.