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

Xenobiotica

Volumn 26, Issue 11, 1996, Pages 1155-1166

  Ono, S ^a,d,e   Hatanaka, T ^a   Miyazawa, S ^a   Tsutsui, M ^a   Aoyama, T ^b   Gonzalez, F J ^c   Satoh, T ^d  

^a Amersham KK   (Japan)

^b SHINSHU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

^d CHIBA UNIVERSITY   (Japan)

^e Amersham KK   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; DIAZEPAM; DRUG METABOLITE; NORDAZEPAM; TEMAZEPAM;

ARTICLE; CONTROLLED STUDY; DEMETHYLATION; DRUG HYDROXYLATION; DRUG METABOLISM; HUMAN; HUMAN TISSUE; LIVER MICROSOME;

STAPHYLOCOCCUS PHAGE 3A; VACCINIA; VACCINIA VIRUS;

EID: 0029974085     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.3109/00498259609050260     Document Type: Article

References (38)

1. ABDEL-HAMID, M. E. and ABUIRJEIE, M. A., 1988, Determination of diazepam and oxazepam using high-performance liquid chromatography and fourth-derivative spectrophotometric techniques. Analyst, 113, 1443-1446.
2. ANDERSSON, T., MINERS, J. O., VERONESE, M. E., and BIRKETT, D. J., 1994, Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. British Journal of Clinical Pharmacology, 38, 131-137.
3. 1. Proceedings of the National Academy of Sciences, USA, 87, 4790-4793.
4. AOYAMA, T., YAMANO, S., WAXMAN, D. J., LAPENSON, D. P., MEYER, U. A., FISCHER, V., TYNDALE, R., INABA, T., KALOW, W., GELBOIN, H. V., and GONZALEZ, F. J., 1989, Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. Journal of Biological Chemistry, 264, 10388-10395.
5. BEISHLAG, T. V., KALOW, W., MAHON, W. A., and INABA, T., 1992, Diazepam metabolism by rat and human liver in vitro: inhibition by mephenytoin. Xenobiotica, 22, 559-567.
6. BERTILSSON, L., HENTHORN, T. K., SANZ, E., TYBRING, G., SÄWE, J., and VILLEN, T., 1989, Importance of genetic factors in the regulation of diazepam metabolism: relationship to S-mephenytoin, but not debrisoquin, hydroxylation phenotype. Clinical Pharmacology and Therapeutics, 45, 348-355.
7. CHEN, L.-S., YASUMORI, T., YAMAZOE, Y., and KATO, K., 1993, Hepatic microsomal tolbutamide hydroxylation in Japanese : in vitro evidence for rapid and slow metabolizers. Pharmacogenetics, 3, 77-85.
8. DE MORAIS, S. M., WILKINSON, G. R., BLAISDELL, J., MEYER, U. A., NAKAMURA, K., and GOLDSTEIN, J. A., 1994, Identification of a new genetic defect responsible for the polymorphism of (S)-mephenytoin metabolism in Japanese. Molecular Pharmacology, 46, 594-598.
9. DE MORAIS, S. M., WILKINSON, G. R., BLAISDELL, J., NAKAMURA, K., MEYER, U. A., and GOLDSTEIN, J. A., 1994, The major genetic detect responsible for the polymorphism of S-mephenytoin metabolism in humans. Journal of Biological Chemistry, 269, 15419-15422.
10. FLAMMANG, A. M., GELBOIN, H. V., AOYAMA, T., GONZALEZ, F. J., and MCCOY, G. D., 1992, Nicotine metabolism by cDNA-expressed human cytochrome P-450s. Biochemical Archives, 8, 1-8.
11. GOLDSTEIN, J. A., FALETTO, M. B., ROMKES-SPARKS, M., SULLIVIAN, T., KITAREEWAN, S., RAUCY, J. L., LASKER, J. M., and GHANAYEM, B. I., 1994a, Evidence that CYP2C19 is the major (S)-mephenytom 4′-hydroxylase in humans. Biochemistry, 33, 1743-1752.
12. GOLDSTEIN, J. A. and DE MORAIS, S. M. F., 1994b, Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics, 4, 285-299.
13. GOLDSTEIN, J. A., WILKINSON, G. R., NAKAMUKA, K., MEYER, U. A., and DE MORAIS, S. M. F., 1994c, Identification of the major defect responsible for the mephenytoin hydroxylase polymorphism in humans. 10th Internal symposium on microsomes and drug oxidations, Toronto, July, 134-135.
14. GONZALEZ, F. J., AOYAMA, T., and GELBOIN, H. V., 1991, Expression of mammalian cytochrome P450 using vaccinia virus. In Methods of Enzymology, edited by M. R. Waterman and E. F. Johnson (San Diego: Academic), 206, 85-92.
15. HORAI, Y., NAKANO, M., ISHIZAKI, T., ISHIKAWA, K., ZHOU, H. H., ZHOU, B. I., LIAO, C. L., and ZHANG, L. M., 1989, Metoprolol and mephenytoin oxidation polymorphism in Far Eastern Oriental subjects: Japanese versus mainland Chinese. Clinical Pharmacology and Therapeutics, 46, 198-207.
16. IMAOKA, S., TERANO, Y., and FUNAE, Y., 1989, Expression of four phenobarbital-inducible cytochrome P-450s in liver, kidney, and lung of rats. Journal of Biochemistry, 105, 939-945.
17. KIMURA, S., PASTEWKA, J., GELBOIN, H. V., and GONZALEZ, F. J., 1987, cDNA and amino acid sequences of two members of the human IIC gene subfamily. Nucleic Acids Research, 15, 10053-10054.
18. KOLARS, J. C., LOWN, K. S., SCHMIEDLIN-REN, P., GHOSH, M., FANG, C., WRIGHTON, S. A., MERION, R. M., and WATKINS, P. B., 1994, CYP3A gene expression in human gut epithelium. Pharmacogenetics, 4, 247-259.
19. KOLARS, J. C., SCHMIEDLIN-REN, P., SCHUETZ, J. D., FANG, C., and WATKINS, P. B., 1992, Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. Journal of Clinical Investigation, 90, 1871-1878.
20. NAKAMURA, K., GOTO, F., RAY, W. A., MCALLISTER, C. B., JACQZ, E., WILKINSON, G. R., and BRANCH, R. A., 1985, Interethnic differences in genetic polymorphism of debrisoquin and mephenytoin hydroxylation between Japanese and Caucasian populations. Clinical Pharmacology and Therapeutics, 38, 402-408.
21. 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., and NEBERT, D. W., 1993, The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biology, 12, 1-51.
22. ONO, S., HATANAKA, T., HOTTA, H., SATOH, T., GONZALEZ, F. J., and TSUTSUI, M., 1996, Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica, 26, 681-693.
23. ONO, S., HATANAKA, T., HOTTA, H., TSUTSUI, M., SATOH, T., and GONZALEZ, F. J., 1995b, Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics, 5, 143-150.
24. 2) using recombinant vaccinia virus. Pharmacogenetics, 5, 97-102.
25. RELLING, M. V., AOYAMA, T., GONZALEZ, F. J., and MEYER, U. A., 1990, Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. Journal of Pharmacology and Experimental Therapeutics, 252, 442-447.
26. RETTIE, A. E., KORZEKWA, K. R., KUNZE, K. L., LAWRENCE, R. F., EDDY, A. C., AOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J., and TRAGER, W. F., 1992, 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, 5, 54-59.
27. SCHUETZ, J. D., BEACH, D. L., and GUZELIAN, P. S., 1994, Selective expression of cytochrome P450 CYP3A mRNAs in embrionic and adult human liver. Pharmacogenetics, 4, 11-20.
28. SHIMADA, T., MISONO, K. S., and GUENGERICH, F. P., 1986, Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 261, 909-921.
29. SHIMADA, T., YAMAZAKI, H., MIMURA, M., INUI, Y., and GUENGERICH, F. P., 1994, 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, 270, 414-423.
30. SOHN, D. R., KUSAKA, M., ISHIZAKI, T., SHIN, S. G., JANG, I. J., SHIN, J. G., and CHIBA, K., 1992, Incidence of S-mephenytoin hydroxylation deficiency in a Korean population and the interphenotypic differences in diazepam pharmacokinetics. Clinical Pharmacology and Therapeutics, 52, 160-169.
31. WATKINS, P. B., WRIGHTSON, S. A., SCHUETZ, E. G., MOLOWA, D. T., and GUZELIAN, P. S., 1987, Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. Journal of Clinical Investigations, 80, 1029-1036.
32. WILKINSON, G. R., GUENGERICH, F. P., and BRANCH, R. A., 1989, Genetic polymorphism of S-mephenytoin hydroxylation. Pharmacological Therapeutics, 43, 53-76.
33. YAMANO, S., AOYAMA, T., MCBRIDE, O. W., HARDWICK, J. P., GELBOIN, H. V., and GONZALEZ, F. J., 1989a, 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, 35, 83-88.
34. YAMANO, S., NHAMBURO, P. T., AOYAMA, T., MEYER, U. A., INABA, T., KALOW, W., GELBOIN, H. V., MCBRIDE, O. W., and GONZALEZ, F. J., 1989b, 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, 28, 7340-7348.
35. YAMANO, S., TATSUNO, J., and GONZALEZ, K. J., 1990, The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry, 29, 1322-1329.
36. YASUMORI, T., MURAYAMA, N., YAMAZOE, Y., and KATO, R., 1990, Polymorphism in hydroxylation of mephenytoin and hexobarbital stereoisomers in relation to hepatic P-450 human-2. Clinical Pharmacology and Therapeutics, 47, 313-322.
37. YASUMORI, T., NAGATA, K., YANG, S. K., CHEN, L.-S., MURAYAMA, N., YAMAZOE, Y., and KATO, R., 1993, Cytochrome P450 mediated metabolism of diazepam in human and rat: involvement of human CYP2C in N-demethylation in the substrate concentration-dependent manner. Pharmacogenetics, 3, 291-301.
38. m diazepam N-demethylase in livers of poor metabolizers for S-mephenytoin 4′-hydroxylation. Pharmacogenetics, 4, 323-331.