Identification of cytochrome P450 isozymes involved in metabolism of the α₁-adrenoceptor blocker tamsulosin in human liver microsomes

References

• BALDWIN, S. J., BLOOMER, J. C., SMITH, G. J., AYRTON, A. C., CLARKE, S. E. and CHENERY, R. J., 1995, Ketoconazole and sulphaphenazole as the respective selective inhibitors of P453A and 2C9. Xenobiotica, 25, 261–270.
   PubMed Web of Science ®Google Scholar
• BRAWER, M. K., 1993, The role of alpha-blockade in benign prostatic hyperplasia. Journal of Clinical Pharmacology, 33, 891–895.
   PubMed Web of Science ®Google Scholar
• BRIAN, W. R., SRIVASTAVA, P. K., UMBENHAUER, D. R., LLOYD, R. S. and GUENGERICH, F. P., 1989, Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in Saccharomyces cerevisiae. Biochemistry, 28, 4993–4999.
   PubMed Web of Science ®Google Scholar
• CRESPI, C. L., PENMAN, B. W., GELBOIN, H. V. and GONZALEZ, F. J., 1991, A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridy1)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis, 12, 1197–1201.
   PubMed Web of Science ®Google Scholar
• DIRVEN, H. A. A. M., PETERS, J. G. P., GIBSON, G. G., PETERS, W. H. M. and JONGENEELEN, F. J., 1991, Lauric acid hydroxylase activity and cytochrome P450 IV family proteins in human liver microsomes. Biochemical Pharmacology, 42, 1841–1844.
   Google Scholar
• DISTLERATH, L. M., REILLY, P. E. B., MARTIN, M. V., DAVIS, G. G., WILKINSON, G. R. and GUENGERICH, F. P., 1985, Purification and characterization of the human cytochromes P450 involved in debrisoquine 4-hydroxylation and phenacetin 0-deethylation, two prototypes for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 260, 9075–9067.
   Google Scholar
• FORRESTER, L. M., HENDERSON, C. J., GLANCEY, M. J., BACK, D. J., PARK, B. K., BALL, S. E., KITTERINGHAM, N. R., MCLAREN, A. W., MILES, J. S., SKETT, P. and WOLF, C. R., 1992, Relative expression of cytochrome P450 isoenzymes in human liver and association with the metabolism of drugs and xenobiotics. Biochemical Journal, 281, 359–368.
   PubMed Web of Science ®Google Scholar
• FRANKLIN, M. R., 1977, Inhibition of mixed-function oxidations by substrates forming reduced cytochrome P-450 metabolic-intermediate complexes. Pharmacology and Therapeutics, A, 2, 227–245.
   Web of Science ®Google Scholar
• GOLDSTEIN, J. A., FALETTO, M. B., ROMKF_S -SPARKS, M., SULLIVAN, T., KITAREEWAN, S., RAUCY, J. L., LASKER, J. M. and GHANAYEM, B. I., 1994, Evidence that CYP2C9 is the major (S)-mephenytoin 4'-hydroxylase in humans. Biochemistry, 33, 1743–1752.
   Google Scholar
• GONZALEZ, F. J., 1992, Human cytochromes P450: problems and prospects. Trends in Pharmacological Sciences, 13, 346–352.
   PubMed Web of Science ®Google Scholar
• GUENGERICH, F. P., MULLER -ENOCH, D. and BLAIR, I. A., 1986, Oxidation of quinidine by human liver cytochrome P-450. Molecular Pharmacology, 30, 287–295.
   Google Scholar
• VAN HOOGDALEM, E. J., SOEISHI, Y., MATSUSHIIVIA, H. and HIGUCHI, S., 1997, Disposition of the selective a,A-adrenoceptor antagonist tamsulosin in humans; comparison with data from interspecies scaling. Journal of Pharmaceutical Sciences, 86, 1156–1161.
   PubMed Web of Science ®Google Scholar
• ISOGAI, M., SHIMADA, N., KAMATAKI, T., IMAOKA, S. and FUNAE, Y., 1993, Changes in the amounts of cytochrome P450 in rat hepatic microsomes produced by cyclosporin A. Xenobiotica, 23, 799–807.
   PubMed Web of Science ®Google Scholar
• KAWASHIMA, H., KUSUNOSE, E., KIKUTA, Y., KINOSHITA, H., TANAKA, S., YAMAMOTO, S., KISHIMOTO T and KUSUNOSE, M., 1994, Purification and cDNA cloning of human liver CYP4A fatty acid co-hydroxylase. Journal of Biochemistry (Tokyo), 116, 74–80.
   Google Scholar
• KNODELL, R. G., BROWNE, D. G., GWOZDZ, G. P., BRIAN, W. R. and GUENGERICH, F. P., 1991, Differential inhibition of individual human liver cytochromes P-450 by cimetidine. Gastro-enterology, 101, 1680–1691.
   PubMed Web of Science ®Google Scholar
• KNODELL, R. G., DusEv, R. K., WILKINSON, G. R. and GUENGERICH, F. P., 1988, Oxidative metabolism of hexobarbital in human liver: relationship to polymorphic S-mephenytoin 4-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 245, 845–849.
   PubMed Web of Science ®Google Scholar
• Liu, G., GELBOIN, H. V. and MYERS, M. J., 1991, Role of cytochrome P450 1A2 in acetanilide 4-hydroxylation as determined with cDNA expression and monoclonal antibodies. Archives of Biochemistry and Biophysics, 284, 400–406.
   PubMed Web of Science ®Google Scholar
• LOWRY, 0. 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.
   Google Scholar
• MAURICE, M., PICHARD, L., DAUJAT, M., FABRE, I., JOYEUX, H., DOMERGUE, J. and MAUREL, P., 1992, Effects of imidazole derivatives on cytochrome P450 from human hepatocytes in primary culture. FASEB Journal, 6, 752–758.
   PubMed Web of Science ®Google Scholar
• MINERS, J. 0., ROBSON, R. A., McMANus, M. E., VERONESE, M. E. and BIRKETT, D. J., 1988, Tolbutamide hydroxylation by human liver microsomes: kinetic characterization and relationship to other cytochrome P-450 dependent xenobiotic oxidations. Biochemical Pharmacology, 37, 1137–1144.
   Google Scholar
• OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence of its hemoprotein nature. Journal of Biological Chemistry, 239, 2370–2378.
   PubMed Web of Science ®Google Scholar
• OTTON, S. V., BRINN, R. U. and GRAM, L. F., 1988b, In vitro evidence against the oxidation of quinidine by the sparteine/debrisoquine monooxygenase of human liver. Drug Metabolism and Disposition, 16, 15–17.
   PubMed Web of Science ®Google Scholar
• OTTON, S. V., CREW, H. K., LENNARD, M. S., TUCKER, G. T. and WOODS, H. F., 1988a, Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P-450 in metoprolol oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 247, 242–247.
   PubMed Web of Science ®Google Scholar
• OTTON, S. V., INABA, T. and KALO W., 1984, Competitive inhibition of sparteine oxidation in human liver by )3-adrenoceptor antagonists and other cardiovascular agents. Life Science, 34, 73–80.
   PubMed Web of Science ®Google Scholar
• PEARCE, R., GREENWAY, D. and PARKINSON, A., 1992, Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: effects on coumarin, dicumarol, and testosterone oxidation. Archives of Biochemistry and Biophysics, 298, 211–225.
   PubMed Web of Science ®Google Scholar
• PEARCE, R. E., MCINTYRE, C. J., MADAN, A., SANZGIRI, U., DRAPER, A. J., BULLOCK, P. L., COOK, D. C., BURTON, L. A., LATHAM, J., NEVINS, C. and PARKINSON, A., 1996, Effects of freezing, thawing, and storing human liver microsomes on cytochrome P450 activity. Archives of Biochemistry and Biophysics, 331, 145–169.
   PubMed Web of Science ®Google Scholar
• PENMAN, B. W., REEcE, J., SMITH, T., YANG, C. S., GELBOIN, H. V., GONZALEZ, F. J. and CBEsPi, C. L., 1993, Characterization of a human cell line expressing high levels of cDNA-derived CYP2D6. Pharmacogenetks, 3, 28–39.
   PubMedGoogle Scholar
• PETE R., BöCKER, R., BEAUNE, P. H., IWASAKI, M., GUENGERICH, F. P. and YANG, C. S., 1990, Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450 IIEL Chemical Research in Toxicology, 3, 566–573.
   Google Scholar
• REIDY, G. F., MEHTA I. and MURRAY, M., 1989, Inhibition of oxidative drug metabolism by orphenadrine: in vitro and in vivo evidence for isozyme-specific complexation of cytochrome P-450 and inhibition kinetics. Molecular Pharmacology, 35, 736–743.
   Google Scholar
• RELLING, M. V., AOYAMA, T., GONZALEZ, F. J. and MEYER, U. A., 1990, Tolbutamide and mephenytoin hydroxylation by human cytochrome P45 Os in the CYP2C subfamily. Journal of Pharmacology and Experimental Therapeutics, 252, 442–447.
   PubMed Web of Science ®Google Scholar
• SCHMID, B., BIRCHER, J., PREISIG, R. and KIJPFER, A., 1985, Polymorphic dextromethorphan metabolism: co-segregation of oxidative 0-demethylation with debrisoquin hydroxylation. Clinical Phar-macology and Therapeutics, 38, 618–624.
   PubMed Web of Science ®Google Scholar
• SMITH, S. R. and KENDALL, M. J., 1988, Ranitidine versus cimetidine: a comparison of their potential to cause clinically important drug interactions. Clinical Pharmacokinetics, 15, 44–56.
   PubMed Web of Science ®Google Scholar
• SOEISHI, Y., MATSUSHIMA, H., TERAYA, Y., WATANABE, T., HIGUCHI, S. and KANIWA, H., 1996b, Metabolism of tamsulosin in rat and dog. Xenobiotka, 26, 355–365.
   PubMed Web of Science ®Google Scholar
• SOEISHI, Y., MATSUSHIMA, H., WATANABE, T., HIGUCHI, S., CORNELISSEN, K. and WARD, J., 1996a, Absorption, metabolism and excretion of tamsulosin hydrochloride in man. Xenobiotica, 26, 637–645.
   PubMed Web of Science ®Google Scholar
• SPEEG, K. V., MEREDITH, C. G. and MALDONADO, A. L., 1983, Ketoconazole inhibits hepatic oxidative drug metabolism. Hepatology, 3, 860–861.
   Google Scholar
• SPINLER, S. A., CHENG J. W., KINDWALL, K. E. and CHARLAND, S. L., 1995, Possible inhibition of hepatic metabolism of quinidine by erythromycin. Clinical Pharmacology and Therapeutics, 57, 89–94.
   Google Scholar
• SRIVASTAVA, P. K., Yu, C-H., BEAUNE, P. H., GED, C. and GUENGERICH, F. P., 1991, Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4'-hydroxylase cyto-chrome P-450 enzymes. Molecular Pharmacology, 40, 69–79.
   Google Scholar
• STARKEY, L. P., YASUKAWA, K., TRENGA, C., MIYAZAYA, Y. and Ho, Y., 1994, Study of possible pharmacodynamic interaction between tamsulosin and nifedipine in subjects with essential hypertension. Journal of Clinical Pharmacology, 34, 1019.
   Google Scholar
• TAGUCHI, K., SAITOH, M., SATO, S., ASANO, M. and MICHEL, M. C., 1997, Effects of tamsulosin metabolites at a-adrenoceptor subtypes. Journal of Pharmacology and Experimental Therapeutics, 280, 1–5.
   PubMed Web of Science ®Google Scholar
• TASSANEEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELOBOIN H. V. and MINERS, J. 0. 1993a, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401–407.
   Google Scholar
• TASSANEEYAKUL W., VERONESE, M. E., BIRKETT, D. J., GONZALEZ, F. J. and MINERS, J. 0., 1993b, Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochemical Pharmacology, 46, 1975–1981.
   Google Scholar
• WATKINs, P. B., MURRAY, S. A., WINKELMAN, L. G., HEUMAN, D. M., WRIGHTON, S. A. and GuELIAN, P. S., 1989, Erythromycin breath test as an assay of glucocorticoid-inducible liver cytochromes P-450. Journal of Clinical Investigation, 83, 688–697.
   PubMed Web of Science ®Google Scholar
• WATKINs, P. B., WRIGHTON, S. A., MAUREL, P., SCHUETZ, E. G., MENDEZ -PICON, G., PARKER, G. A. and GUZELIAN, P. S., 1985, Identification of an inducible form of cytochrome P-450 in human liver. Proceedings of National Academic Sciences, USA, 82, 6310–6314.
   Google Scholar
• WAXMAN, D. J., ATTISANO, C., GUENGERICH, F. P. and LAPENSON, D. P., 1988, Human liver microsomal steroid metabolism: identification of the major microsomal steroid hormone 6/3-hydroxylase cytochrome P-450 enzyme. Archives of Biochemistry and Biophysics, 263, 424–436.
   PubMed Web of Science ®Google Scholar
• WRIGHTON, S. A. and RING, B. J., 1994, Inhibition of human CYP3A catalyzed V-hydroxy midazolam formation by ketoconazole, nifedipine, erythromycin, cimetidine, and nizatidine. Pharmaceutical Research, 11, 921–924.
   PubMed Web of Science ®Google Scholar
• WRIGHTON, S. A., STEVENS, J. C., BECKER, G. W. and VANDEN BRANDEN, M., 1993, Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin C.-hydroxylation. Archives of Biochemistry and Biophysics, 306, 240–245.
   PubMed Web of Science ®Google Scholar
• YAMADA, S., TANAKA, C., KIMURA, R. and KAWABE, K., 1994, Alpha adrenoceptors in human prostate: characterization and binding characteristics of alpha -antagonists. Life Sciences, 54, 1845–1854.
   PubMed Web of Science ®Google Scholar