Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: Role of CYP2B6, 2C19 and the 3A subfamily

References

• Abdel-Hamid M. E., Abuirjeie M. A. Determination of diazepam and oxazepam using high-performance liquid chromatography and fourth-derivative spectrophotometric techniques. Analyst 1988; 113: 1443–1446
   PubMed Web of Science ®Google Scholar
• Andersson T., Miners J. O., Veronese M. E., Birkett D. J. Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. British Journal of Clinical Pharmacology 1994; 38: 131–137
   PubMed Web of Science ®Google Scholar
• Aoyama T., Yamano S., Guzelian P. S., Gelboin H. V., Gonzalez F. J. Five of 12 forms of vaccinia virus-expressed human hepatic cytochrome P450 metabolically active aflatoxin B1. Proceedings of the National Academy of Sciences, USA 1990; 87: 4790–4793
   PubMed Web of Science ®Google Scholar
• Aoyama T., Yamano S., Waxman D. J., Lapenson D. P., Meyer U. A., Fischer V., Tyndale R., Inaba T., Kalow W., Gelboin H. V., Gonzalez F. J. Cytcchrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. Journal of Biological Chemistry 1989; 264: 10388–30393
   PubMed Web of Science ®Google Scholar
• Beishlag T. V., Kalow W., Mahon W. A., Inaba T. Diazepam metabolism by rat and human liver in vitro: Inhibition by mephenytoin. Xenobiotica 1992; 22: 559–567
   PubMedGoogle Scholar
• Bertilsson L., Henthorn T. K., Sanz E., Tybring G., Säwe J., Villen T. Importance of genetic factors in the regulation of diazepam metabolism: relationship to S-mephenytoin, but not debrisoquin, hydroxylation phenotype. Clinical Pharmacology and Therapeutics 1989; 45: 348–355
   PubMed Web of Science ®Google Scholar
• Chen L.-S., Yasumori T., Yamazoe Y., Kato R. Hepatic microsomal tolbutamide hydroxylation in Japanese: in vitro evidence for rapid and slow metabolizers. Pharmacogenetics 1993; 3: 77–85
   PubMedGoogle Scholar
• de Morais S. M., Wilkinson G. R., Blaisdell J., Meyer U. A., Nakamura K., Goldstein J. A. Identification of a new genetic defect responsible for the polymorphism of (S)-mephenytoin metabolism in Japanese. Molecular Pharmacology 1994; 46: 594–598
   PubMed Web of Science ®Google Scholar
• de Morais S. M., Wilkinson G. R., Blaisdell J., Nakamura K., Meyer U. A., Goldstein J. A. The major genetic defect responsible for the polymorphism of S-mephenytoin metabolism in humans. Journal of Biological Chemistry 1994; 269: 15419–15422
   PubMed Web of Science ®Google Scholar
• Flammang A. M., Gelboin H. V., Aoyama T., Gonzalez F. J., McCoy G. D. Nicotine metabolism by cDNA-expressed human cytochrome P-450s. Biochemical Archives 1992; 8: 1–8
   Google Scholar
• Goldstein J. A., Faletto M. B., Romkes-Sparks M., Sullivian T., Kitareewan S., Raucy J. L., Lasker J. M., Ghanayem B. I. Evidence that CYP2C19 is the major (S)-mephenytoin 4′-hydroxylase in humans. Biochemistry 1994a; 33: 1743–1752
   PubMed Web of Science ®Google Scholar
• Goldstein J. A., de Morais S. M. F. Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics 1994b; 4: 285–299
   PubMedGoogle Scholar
• Goldstein J. A., Wilkinson G. R., Nakamura K., Meyer U. A., de Morais S. M. F. Identification of the major defect responsible for the mephenytoin hydroxylase polymorphism in humans. 10th Internal symposium on microsomes and drug oxidations, Toronto, 1994c, 134–135, July
   Google Scholar
• Gonzalez F. J., Aoyama T., Gelboin H. V. Expression of mammalian cytochrome P450 using vaccinia virus. Methods of Enzymology, M. R. Waterman, E. F. Johnson. Academic, San Diego 1991; 206, 85–92
   Google Scholar
• Horai Y., Nakano M., Ishizaki T., Ishikawa K., Zhou H. H., Zhou B. I., Liao C. L., Zhang L. M. Metoprolol and mephenytoin oxidation polymorphism in Far Eastern Oriental subjects: Japanese versus mainland Chinese. Clinical Pharmacology and Therapeutics 1989; 46: 198–207
   PubMed Web of Science ®Google Scholar
• Imaoka S., Terano Y., Funae Y. Expression of four phenobarbital-inducible cytochrome P-450s in liver, kidney, and lung of rats. Journal of Biochemistry 1989; 105: 939–945
   PubMed Web of Science ®Google Scholar
• Kimura S., Pastewka J., Gelboin H. V., Gonzalez F. J. cDNA and amino acid sequences of two members of the human IIC gene subfamily. Nucleic Acids Research 1987; 15: 10053–10054
   PubMed Web of Science ®Google Scholar
• Kolars J. C., Lown K. S., Schmiedlin-Ren P., Ghosh M., Fang C., Wrighton S. A., Merion R. M., Watkins P. B. CYP3A gene expression in human gut epithelium. Pharmacogenetics 1994; 4: 247–259
   PubMedGoogle Scholar
• Kolars J. C., Schmiedlin-Ren P., Schuetz J. D., Fang C., Watkins P. B. Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. Journal of Clinical Investigation 1992; 90: 1871–1878
   PubMed Web of Science ®Google Scholar
• Nakamura K., Goto F., Ray W. A., McAllister C. B., Jacqz E., Wilkinson G. R., Branch R. A. Interethnic differences in genetic polymorphism of debrisoquin and mephenytoin hydroxylation between Japanese and Caucasian populations. Clinical Pharmacology and Therapeutics 1985; 38: 402–408
   PubMed Web of Science ®Google Scholar
• Nelson D. R., Kamataki T., Waxman D. J., Guengerich F. P., Estabrook R. W., Feyereinsen R., Gonzalez F. J., Coon M. J., Gunsalus I. C., Gotoh O., Okuda K., Nebert D. W. The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biology 1993; 12: 1–51
   PubMed Web of Science ®Google Scholar
• Ono S., Hatanaka T., Hotta H., Satoh T., Gonzalez F. J., Tsutsui M. Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica 1996; 26: 681–693
   PubMed Web of Science ®Google Scholar
• Ono S., Hatanaka T., Hotta H., Tsutsui M., Satoh T., Gonzalez F. J. Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics 1995b; 5: 143–150
   PubMedGoogle Scholar
• Ono S., Tsutsui M., Gonzalez F. J., Satoh T., Masubuchi Y., Horie T., Suzuki T., Narimatsu S. Oxidative metabolism of bunitrolol by complementary DNA-expressed human cytochrome P450 isozymes in a human hepatoma cell line (Hep G2) using recombinant vaccinia virus. Pharmacogenetics 1995a; 5: 97–102
   PubMedGoogle Scholar
• Relling M. V., Aoyama T., Gonzalez F. J., Meyer U. A. Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. Journal of Pharmacology and Experimental Therapeutics 1990; 252: 442–447
   PubMed Web of Science ®Google Scholar
• Rettie A. E., Korzekwa K. R., Kunze K. L., Lawrence R. F., Eddy A. C., Aoyama T., Gelboin H. V., Gonzalez F. J., Trager W. F. Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: a role for P-4502C9 in the etiology of (S)-warfarin-drug interractions. Chemical Research and Toxicology 1992; 5: 54–59
   PubMed Web of Science ®Google Scholar
• Schuetz J. D., Beach D. L., Guzelian P. S. Selective expression of cytochrome P450 CYP3A mRMAs in embrionic and adult human liver. Pharmacogenetics 1994; 4: 11–20
   PubMedGoogle Scholar
• Shimada T., Misono K. S., Guengerich F. P. Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry 1986; 261: 909–921
   PubMed Web of Science ®Google Scholar
• Shimada T., Yamazaki H., Mimura M., Inui Y., Guengerich F. P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics 1994; 270: 414–423
   PubMed Web of Science ®Google Scholar
• Sohn D. R., Kusaka M., Ishizaki T., Shin S. G., Jang I. J., Shin J. G., Chiba K. Incidence of S-mephenytoin hydroxylation deficiency in a Korean population and the interphenotypic differences in diazepam pharmacokinetics. Clinical Pharmacology and Therapeutics 1992; 52: 160–169
   PubMed Web of Science ®Google Scholar
• Watkins P. B., Wrightson S. A., Schuetz E. G., Molowa D. T., Guzelian P. S. Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. Journal of Clinical Investigations 1987; 80: 1029–1036
   PubMed Web of Science ®Google Scholar
• Wilkinson G. R., Guengerich F. P., Branch R. A. Genetic polymorphism of S-mephenytoin hydroxylation. Pharmacological Therapeutics 1989; 43: 53–76
   PubMed Web of Science ®Google Scholar
• Yamano S., Aoyama T., McBride O. W., Hardwick J. P., Gelboin H. V., Gonzalez F. J. Human NADPH-P450 oxido-reductase: complementary DNA cloning, sequence and vaccinia virus-mediated expression and localization of the CYPOR gene to chromosome 7. Molecular Pharmacology 1989a; 35: 83–88
   Google Scholar
• Yamano S., Nhamburo P. T., Aoyama T., Meyer U. A., Inaba T., Kalow W., Gelboin H. V., McBride O. W., Gonzalez F. J. cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver. Biochemistry 1989b; 28: 7340–7348
   PubMed Web of Science ®Google Scholar
• Yamano S., Tatsuno J., Gonzalez F. J. The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 1990; 29: 1322–1329
   PubMed Web of Science ®Google Scholar
• Yasumori T., Murayama N., Yamazoe Y., Kato R. Polymorphism in hydroxylation of mephenytoin and hexobarbital stereoisomers in relation to hepatic P-450 human-2. Clinical Pharmacology and Therapeutics 1990; 47: 313–322
   PubMed Web of Science ®Google Scholar
• Yasumori T., Nagata K., Yang S. K., Chen L.-S., Murayama N., Yamazoe Y., Kato R. Cytochrome P450 mediated metabolism of diazepam in human and rat: involvement of human CYP2C in N-demethylation in the substrate concentration-dependent manner. Pharmacogemtics 1993; 3: 291–301
   PubMedGoogle Scholar
• Yasumori T., Qing-hua L., Yamazoe Y., Ueda M., Tsuzuki T., Kato R. Lack of low Km diazepam N-demethylase in livers of poor metabolizers for S-mephenytoin 4′-hydroxylation. Pharmacogenetics 1994; 4: 323–331
   PubMedGoogle Scholar