Role of specific cytochrome P450 enzymes in the N-oxidation of the antiarrhythmic agent mexiletine

References

• ABOLFATHI, Z., FISET, C., GILBERT, M., MOERIKE, K., BELANGER, P. M. and TURGEON, J., 1993, Role of polymorphic debrisoquin 4-hydroxylase activity in the stereoselective disposition of mexiletine in humans. Journal of Pharmacology and Experimental Therapeutics, 266, 1196–1201.
   PubMed Web of Science ®Google Scholar
• BECKETT, A. H., HAYA, K., JoNEs, G. R. and MORGAN, P. H., 1975, Synthetic routes to optical isomers of primary and secondary hydroxylamines of 1-arylisopropylamines. Tetrahedron, 31, 531–1535.
   Web of Science ®Google Scholar
• BROSEN, K., SKJELBO, E., RASMUSSEN, B. B., POLUSEN, H. E. and LOFT, S., 1993, Fluvoxamine is a potent inhibitor of cytochrome P4501A2. Biochemical Pharmacology, 45, 1211–1214.
   PubMed Web of Science ®Google Scholar
• CAMPBELL, R. W. F., 1987, Mexiletine. New England Journal of Medicine, 316, 29–34.
   PubMed Web of Science ®Google Scholar
• CAMPBELL, R. W. F., DOLDER, M. A., PRESCOTT, L. F., TALBOT, R. G., MURRAY, A. and JULIAN, D. G., 1975, Comparison of procainamide and mexiletine in prevention of ventricular arrhythmias after acute myocardial infarction. Lancet, i, 1257–1260.
   Web of Science ®Google Scholar
• FUHR, U., STROBL, G., MANAUT, F., ANDERS, E. M., SORGEL, F., LOPEZ-DE-BRINAS, E., CHU, D. T. W., PERNET, A. G., MAHR, G., SANZ, F. and STAIB, A. H., 1993, Quinolone antibacterial agents: relationship between structure and in vitro inhibition of the human cytochrome P450 isoform CYP1A2. Molecular Pharmacology, 43, 191–199.
   Google Scholar
• GRECH-BELANGER, O., GILBERT, M., TURGEON, J. and LEBLANC, P. P., 1985, Effect of cigarette smoking on mexiletine kinetics. Clinical Pharmacology and Therapeutics, 37, 638–643.
   PubMed Web of Science ®Google Scholar
• GRECH-BELANGER, O., TURGEON, J. and GILBERT, M., 1986, Stereoselective disposition of mexiletine in man. British Journal of Clinical Pharmacology, 21, 481–487.
   PubMed Web of Science ®Google Scholar
• HASELBARTH, V., DOEVENDANS, J. E. and WOLF, M., 1981, Kinetics and bioavailability of mexiletine in healthy subjects. Clinical Pharmacology and Therapeutics, 29, 729–736.
   PubMed Web of Science ®Google Scholar
• HOENER, B. A., 1994, Predicting the hepatic clearance of xenobiotics in humans from in vitro data. Biopharmacology and Drug Disposition, 15, 295–304.
   PubMed Web of Science ®Google Scholar
• HURWITZ, A., VACEK, J. L., BOTTERON, G. W., SZTERN, M. I., HUGHES, E. M. and JAYARAJ, A., 1991, Mexiletine effects on theophylline disposition. Clinical Pharmacology and Therapeutics, 50, 299–307.
   PubMed Web of Science ®Google Scholar
• JOERES, R., KLINKER, H., HEUSLER, H., EPPING, J. and RICHTER, E., 1987, Influence of mexiletine on caffeine elimination. Pharmacological Therapeutics, 33, 163–169.
   PubMed Web of Science ®Google Scholar
• KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAVIES, D. S. and BOOBIS, A. R., 1989, The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochemical Pharmacology, 38, 2795–2799.
   PubMed Web of Science ®Google Scholar
• KUSUMOTO, M., UENO, K., ODA, A., TAKEDA, K., MASHIMO, K., TAKAYA, K., FUJIMURA, Y., NISHIHORI, T. and TANAKA, K., 2001, Effect of fluvoxamine on the pharmacokinetics of mexiletine in healthy Japanese men. Clinical Pharmacology and Therapeutics, 69, 104–107.
   PubMed Web of Science ®Google Scholar
• LABEE, L., 2000, Metabolisme de la mexiletine chez l'humain: role du CYP1A2 et interaction avec la propafenone. Thesis, Laval University, Quebec.
   Google Scholar
• LABBE, L., ABOLFATHI, Z., ROBITAILLE, N. M., ST-MAURICE, F., GILBERT, M. and TURGEON, J., 1999, Stereoselective disposition of the antiarrhythmic agent mexiletine during the concomitant administration of caffeine. Therapeutics and Drug Monitoring, 21, 191–199.
   Google Scholar
• LOI, C. M., WEI, X. and VESTAL, R. E., 1991, Inhibition of theophylline metabolism by mexiletine in young male and female nonsmokers. Clinical Pharmacology and Therapeutics, 49, 571–580.
   PubMed Web of Science ®Google Scholar
• LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   PubMed Web of Science ®Google Scholar
• MCMANUS, M. E., BURGESS, W. M., VERONESE, M. E., HUGGETT, A., QUATTROCHI, L. C. and TUKEY, R. H., 1990, Metabolism of 2-acetylaminofluorene and benzo(a)pyrene and activation of food-derived heterocyclic amine mutagens by human cytochromes P-450. Cancer Research, 50, 3367–3376 .
   PubMed Web of Science ®Google Scholar
• NAKAJIMA, M., KOBAYASHI, K., SHIMADA, N., TOKUDOME, S., YAMAMOTO, T. and KUROIWA, Y., 1998, Involvement of CYP1A2 in mexiletine metabolism. British Journal of Clinical Pharmacology, 46, 55–62.
   PubMed Web of Science ®Google Scholar
• PENTIKAINEN, P. J., HALINEN, M. O. and HELIN, M. J., 1984. Pharmacokinetics of intravenous mexiletine in patients with acute myocardial infarction. Journal of Cardiovascular Pharmacology, 6, 1–6.
   PubMed Web of Science ®Google Scholar
• PENTIKAINEN, P. J., KOIVULA, I. H. and HILTUNEN, H. A., 1982, Effect of rifampicin treatment on the kinetics of mexiletine. European Journal of Clinical Pharmacology, 23, 261–266.
   PubMed Web of Science ®Google Scholar
• PRESCOTT, L. F., POTTAGE, A. and CLEMENTS, J. A., 1977, Absorption, distribution and elimination of mexiletine. Postgraduate Medical Journal, 53\(suppl. 1), 50–55.
   PubMed Web of Science ®Google Scholar
• SESARDIC, D., BOOBIS, A. R., EDWARDS, R. J. and DAVIES, D. S., 1988, A form of cytochrome P450 in man, orthologous to form d in the rat, catalyses the O-deethylation of phenacetin and is inducible by cigarette smoking. British Journal of Clinical Pharmacology, 26, 363–372.
   PubMed Web of Science ®Google Scholar
• SESARDIC, D., BOOB'S, A. R., MURRAY, B. P., MURRAY, S., SEGURA, J., DE LA TORRE, R. and DAVIES, D. S., 1990, Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man. British Journal of Clinical Pharmacology, 29, 651–663.
   Google Scholar
• STOYSICH, A. M., MOHIUDDIN, S. M., DESTACHE, C. J., NIPPER, H. C. and HILLEMAN, D. E., 1991, Influence of mexiletine on the pharmacokinetics of theophylline in healthy volunteers. Journal of Clinical Pharmacology, 31, 354–357.
   PubMed Web of Science ®Google Scholar
• TASSANEEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., McMANus, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELBOIN, H. V. and MINERS, J. O., 1993, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401–407.
   PubMed Web of Science ®Google Scholar
• TURGEON, J., FISET, C., GIGUERE, R., GILBERT, M., MOERIKE, K., ROULEAU, J. R., KROEMER, H. K., EICHELBAU M., GRECH-BELANGER, O. and BELANGER, P. M., 1991a, Influence of debrisoquine phenotype and of quinidine on mexiletine disposition in man. Journal of Pharmacology and Experimental Therapeutics, 259, 789–798.
   Google Scholar
• TURGEON, J., PARE, J. R. J., LALANDE, M., GRECH-BELANGER, O. and BELANGER, P. M., 1992, Isolation and structural characterization by spectroscopic methods of two glucuronide metabolites of mexiletine after N-oxidation and deamination. Drug Metabolism and Disposition, 20, 762–769.
   Google Scholar
• TURGEON, J., UPRICHARD, A. C. G., BELANGER, P. M., HARRON, D. W. G. and GRECH-BELANGER, O., 1991b, Resolution and electrophysiological effects of mexiletine enantiomers. Journal of Pharmaceutics and Pharmacology, 43, 630–635.
   Google Scholar
• WANG, P. P., BEAUNE, P., KAMINSKY, L. S., DANNAN, G. A., KADLUBAR, F. F., LARREY, D. and GUENGERICH, F. P., 1983, Purification and characterization of six cytochrome P-450 isozymes form human liver microsomes. Biochemistry, 22, 5375–5383.
   PubMed Web of Science ®Google Scholar