In vitro assessment of human cytochrome p450

Xenobiotica

Volumn 28, Issue 12, 1998, Pages 1167-1202

  Clarke, S E ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; ANTIARRHYTHMIC AGENT; BUFURALOL; CAFFEINE; CHLORZOXAZONE; COUMARIN; CYTOCHROME P450; DEBRISOQUINE; DEXTROMETHORPHAN; DICLOFENAC; DISOPYRAMIDE; DNA; ENZYME INHIBITOR; ERYTHROMYCIN; KETOCONAZOLE; LAURIC ACID; METOPROLOL; MIDAZOLAM; NIFEDIPINE; PACLITAXEL; PHENACETIN; PHENYTOIN; PROGUANIL; RETINOL; TACRINE; TESTOSTERONE; TOLBUTAMIDE; UNINDEXED DRUG; WARFARIN; XENOBIOTIC AGENT;

CELL MEMBRANE; DEMETHYLATION; DISSOCIATION CONSTANT; DRUG HYDROXYLATION; DRUG METABOLISM; ENDOPLASMIC RETICULUM; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SPECIFICITY; HUMAN; LIVER MICROSOME; MICHAELIS MENTEN KINETICS; NONHUMAN; PROTEIN EXPRESSION; RECOMBINANT DNA TECHNOLOGY; REGRESSION ANALYSIS; REVIEW;

CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; FORECASTING; HUMANS; ISOENZYMES; KINETICS; PROTEIN ENGINEERING; REGRESSION ANALYSIS; REPRODUCIBILITY OF RESULTS; SUBSTRATE SPECIFICITY;

EID: 0032428779     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982598238877     Document Type: Review

References (213)

1. ABBOT, M. R. and GREEN, C. E., 1995, Cytochrome P450 isoforms in 26 human liver specimens. ISSX Proceedings, 8, 91.
2. ANDERSSON, T., MINERS, J. O., VERONESE, M. E., TASSANEEYAKUL, W., MEYER, U. A. and BIRKETT, D. J., 1993, Identification of human liver cytochrome-P450 isoforms mediating omeprazole metabolism. British Journal of Clinical Pharmacology, 36, 521-530.
3. ANDERSSON, T., MINERS, J. O., VERONESE, M. E. and BIRKETT, D. J., 1994a, Identification of human liver cytochrome-P450 isoforms mediating secondary omeprazole metabolism. British Journal of Clinical Pharmacology, 37, 597-604.
4. ANDERSSON, T., MINERS, J. O., VERONESE, M. E. and BIRKETT, D. J., 1994b, Diazepam metabolism by human liver-microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. British Journal of Clinical Pharmacology, 38, 131-137.
5. AOYAMA, T., GONZALEZ, F. J. and GELBOIN, H. V., 1989a, Human cDNA-expressed cytochrome P450 IA2: mutagen activation and substrate specificity. Molecular Carcinogenesis, 2, 192-198.
6. AOYAMA, T., YAMANO, S., WAXMAN, D. J., LAPENSON, D. P., MEYER, U. A., FISCHER, V., TYNDALE, R., INABA, T., KALOW, W. and GELBOIN, H.V., 1989b, Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. Journal of Biological Chemistry, 264, 10388-10395.
7. BACK, D. J., TJIA, J. F., KARBWANG, J. and COLBERT, J., 1988, In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines. British Journal of Clinical Pharmacology, 26, 23-29.
8. BALDWIN, S. J., BLOOMER, J. C., SMITH, G. J., AYRTON, A. D., CLARKE, S. E. and CHENERY, R. J., 1995, Ketoconazole and sulfaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica, 25, 261-270.
9. BALL, S. E., MAURER, G., ZOLLINGER, M., LADONA, M. and VICKERS, A. E., 1992, Characterization of the cytochrome P-450 gene family responsible for the N-dealkylation of the ergot alkaloid CQA 206-291 in humans. Drug Metabolism and Disposition, 20, 56-63.
10. BARDSLEY, W. G., LEFF, P., KAVANAGH, J. and WAIGHT, R., 1980, Deviations from Michaelis-Menten kinetics: The possibility of complicated curves for simple kinetic schemes and the computer fitting of experimental data for acetylcholinesterase, acid phosphatase, adenosine deaminase, arylsulphatase, benzylamine oxidase, chymotrypsin, fumarase, galactose dehydrogenase, β-galactosidase, lactate dehydrogenase, peroxidase and xanthine oxidase. Biochemical Journal, 187, 739-765.
11. BARNES, H. J., ARLOTTO, M. P. and WATERMAN, M. R., 1991, Expression and enzymatic activity of recombinant cytochrome P450 17-hydroxylase in Escherichia coli. Proceedings of the National Academy of Sciences, USA 88, 5597-5601.
12. BEISCHLAG, T. V., KALOW, W. A., MAHON, W. A. and INABA, T., 1992, Diazepam metabolism by rat and human liver in vitro: inhibition by mephenytoin. Xenobiotica, 22, 559-567.
13. BERTHOU, F., FLINOIS, J. P., RATANASAVANH, D., BEAUNE, P., RICHE, C. and GUILLOUZO, A., 1991, Evidence for the involvement of several cytochromes P-450 in the first steps of caffeine metabolism by human liver microsomes. Drug Metabolism and Disposition, 19, 561-567.
14. BERTHOU, F., RATANASAVANH, D., RICHE, C., PICART, D., VOIRIN, T. and GUILLOUZO, A., 1989, Comparison of caffeine metabolism by slices, microsomes and hepatocyte cultures from adult human liver. Xenobiotica, 19, 401-417.
15. BIRGERSSON, C., MORGAN, E. T., JORNVALL, H. and VON BAHR, C., 1986, Purification of desmethylimipramine and debrisoquine hydroxylating cytochrome P450 from human liver. Biochemical Pharmacology, 35, 3165-3166.
16. BIRKETT, D. J., REES, D., ANDERSSON, T., GONZALEZ, F. J., MINERS, J. O. and VERONESE, M., 1994, Invitro proguanil activation to cycloguanil by human liver-microsomes is mediated by CYP3A isoforms as well as by S-mephenytoin hydroxylase. British Journal of Clinical Pharmacology, 37, 413-120.
17. BLOOMER, J. C., CLARKE, S. E. and CHENERY, R. J., 1995, Determination of P4501A2 activity in human liver-microsomes using [3-C-14-methyl] caffeine. Xenobiotica, 25, 917-927.
18. 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.
19. BRIAN, W. R., SARI, M. A., IWASAKI, M., SHIMADA, T., KAMINSKY, L. S. and GUENGERICH, F. P., 1990, Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry, 29, 11280-11292.
20. BROSEN, K., SKJELBO, E., RASMUSSEN, B. B., POULSEN, H. E. and LOFT, S., 1993, Fluvoxamine is a potent inhibitor of cytochrome P4501A2. Biochemical Pharmacology, 45, 1211-1214.
21. BURKE, M. D., THOMPSON, S., ELCOMBE, C. R., HALPERT, J., HAAPARANTA, T. and MAYER, R. T., 1985, Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P450. Biochemical Pharmacology, 34, 3337-3345.
22. BUTERS, J. T. M., KORZEKWA, K. R., KUNZE, K. L., OMATA, Y., HARDWICK, J. P. and GONZALEZ, F. J., 1994, cDNA-directed expression of human cytochrome-P450 CYP3A4 using baculovirus. Drug Metabolism and Disposition, 22, 688-692.
23. BUTERS, J. T. M., SHOU, M. G., HARDWICK, J. P., KORZEKWA, K. R., GONZALEZ, F. J., SCHMALIX, W. A., BARRENSCHEEN, M., LANDSIEDEL, R., JANZOWSKI, C., EISENBRAND, G., GONZALEZ, F., ELIASSON, E., INGELMANSUNDERG, M., PERCHERMEIER, M., GREIM, H. and DOEHMER, J., 1995, cDNA-directed expression of human cytochrome-P450 CYP1A1 using baculovirus purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification Stable expression of human cytochrome-P450 2E1 in V79 chinese-hamster cells. European Journal of Pharmacology-Environmental Toxicology and Pharmacology Section, 293, 123-131.
24. BUTLER, M. A., IWASAKI, M., GUENGERICH, F. P. and KADLUBAR, F. F., 1989, Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proceedings of the National Academy of Sciences, USA, 86, 7696-7700.
25. CAMPBELL, M. E., GRANT, D. M., INABA, T. and KALOW, W., 1987, Biotransformation of caffeine,paraxanthine, theophylline and theobromine by polycyclic aromatic hydrocarbon-inducible cytochrome(s) P450 in human liver microsomes. Drug Metabolism and Disposition, 15, 237-249.
26. CARRIERE, V., GOASDUFF, T., RATANASAVANH, F. M., GAUTIER, J. C., GUILLOUZO, A., BEAUNE, P. and BERTHOU, F., 1993, Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chemical Research in Toxicology, 6, 852-857.
27. CASTLE, P. J., MERDINK, J. L., OKITA, J. R., WRIGHTON, S. A. and OKITA, R. T., 1995, Human liver lauric acid hydroxylase-activities. Drug Metabolism and Disposition, 23, 1037-1043.
28. CHANG, T. K., GONZALEZ, F. J. and WAXMAN, D. J., 1994, Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Archives of Biochemistry and Biophysics, 311, 437-442.
29. CHANG, T. K., WEBER, G. F., CRESPI, C. L. and WAXMAN, D. J., 1993, Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Research, 53, 5629-5637.
30. CHIBA, K., SAITOH, A., KOYAMA, E., TANI, M., HAYASHI, M. and ISHIZAKI, T., 1994, The role of S-mephenytoin 4′-hydroxylase in imipramine metabolism by human liver-microsomes - a 2-enzyme kinetic-analysis of N-demethylation and 2-hydroxylation. British Journal of Clinical Pharmacology, 37, 237-242.
31. CHING, M. S., LENNARD, M. S., TUCKER, G. T., WOODS, H. F., KELLY, M. E. and KELLY, S. L., 1991, The expression of human cytochrome P450IA1 in the yeast Saccharomyces cerevisiae. Biochemical Pharmacology, 42, 753-758.
32. CHRISTOPHERSON, P. A., MANKOWSKI, D. C., TWEEDIE, D. J. and LAWTON, M. P., 1995, Expression of human cytochromes P450 in insect cells. ISSX Proceedings, 8, 358.
33. CLARKE, S. E., AYRTON, A. D. and CHENERY, R. J., 1994a, Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica, 24, 517-526.
34. CLARKE, S. E., BALDWIN, S. J., BLOOMER, J. C., AYRTON, A. D., SOZIO, R. S. and CHENERY, R. J., 1994b, Lauric acid as a model substrate for the simultaneous determination of cytochrome-P450 2E1 and 4A in hepatic microsomes. Chemical Research in Toxicology, 7, 836-842.
35. COCHRAN, W. G. and COX, G. M., 1957, Experimental Designs, 2nd edn (Chichester: John Wiley).
36. CODE, E. L., CRESPI, C. L., PENMAN, B. W., GONZALEZ, F. J., CHANG, T. and WAXMAN, D. J., 1995, Immunochemical and enzymatic characterization of human hepatic levels of CYP2B6. ISSX Proceedings, 8, 100.
37. COMBALBERT, J., FABRE, I., FABRE, G., DALET, I., DERANCOURT, J., CANO, J. P. and MAUREL, P., 1989, Metabolism of cyclosporin A. IV. Purification and identification of the rifampicin-inducible human liver cytochrome P-450 (cyclosporin A oxidase) as a product of P450IIIA gene subfamily. Drug Metabolism and Disposition, 17, 197-207.
38. CORNBLEET, P. J., 1979, Incorrect least-squares regression coefficients in method comparison analysis. Clinical Chemistry, 25, 432-438.
39. CRESPI, C. L., CODE, E. L., PENMAN, B. W. and WAXMAN, D. J., 1995a, An activity based method for integrating metabolism data from cDNA-expressed cytochrome P450 enzymes to the balance of enzymes in human liver microsomes. ISSX Proceedings, 8, 420.
40. CRESPI, C. L., LANGENBACH, R, and PENMAN, B. W., 1990a, The development of a panel of human cell lines expressing specific human cytochrome P450 cDNAs. Progress in Clinical and Biological Research, 340B, 97-106.
41. CRESPI, C. L., LANGENBACH, R. and PENMAN, B. W., 1993, Human cell lines, derived from AHH-1 TK +/-human lymphoblasts, genetically engineered for expression of cytochromes P450. Toxicology, 82, 104.
42. CRESPI, C. L., PENMAN, B. W., GELBOIN, H. V. and GONZALEZ, F. J., 1991a, A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis, 12, 1197-1201.
43. CRESPI, C. L., PENMAN, B. W., STEIMEL, D. T., GELBOIN, H. V. and GONZALEZ, F. J., 1991b, The development of a human cell line stably expressing human CYP3A4: role in the metabolic activation of aflatoxin B1 and comparison to CYP1A2 and CYP2A3. Carcinogenesis, 12, 355-359.
44. CRESPI, C. L., STEIMEL, D. T., AOYAMA, T., GELBOIN, H. V. and GONZALEZ, F. J., 1990b, Stable expression of human cytochrome P450IA2 cDNA in a human lymphoblastoid cell line: role of the enzyme in the metabolic activation of aflatoxin B1. Molecular Carcinogenesis, 3, 5-8.
45. CRESPI, C. L., STEIMEL, D. T., PENMAN, B. W., KORZEKWA, K. R., FERNANDEZSALGUERO, P., BUTERS, J. T. M., GELBOIN, H. V., GONZALEZ, F. J., IDLE, J. R. and DALY, A. K., 1995b, Comparison of substrate metabolism by wild-type CYP2D6 protein and a variant containing methionine, not valine, at position-374. Pharmacogenetics, 5, 234-243.
46. CRESTEIL, T., MONSARRAT, B., ALVINERIE, P., TRELUYER, J. M., VIEIRA, I. and WRIGHT, M., 1994, Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involves in its biotransformation. Cancer Research, 54, 386-392.
47. DAYER, P., LEEMANN, T. and STRIBERNI, R., 1989, Dextromethorphan O-demethylation in liver microsomes as a prototype reaction to monitor cytochrome P-450 db1 activity. Clinical Pharmacology and Therapeutics, 45, 34-40.
48. DIRVEN, H. A., PETERS, J. G., GIBSON, G. G., PETERS, W. H. and JONGENEELEN, F. J., 1991, Lauric acid hydroxylase activity and cytochrome P450 IV family proteins in human liver microsomes. Biochemical Pharmacology, 42, 1841-1844.
49. DISTERLATH, L. M., REILLY, P. E., MARTIN, M. V., DAVIS, G. G., WILKINSON, G. R. and GUENGERICH, F. P., 1985, Purification and characterization of the human liver cytochromes P450 involved in debrisoquine 4-hydroxylation and phenacetin O-deethylation, two prototypes for genetic polymorphisms in oxidative drug metabolism. Journal of Biological Chemistry, 260, 9057-9067.
50. DOECKE, C. J., SANSOM, L. N. and MCMANUS, M. E., 1990, Phenytoin 4-hydroxylation by rabbit liver P450IIC3 and identification of orthologs in human liver microsomes. Biochemical and Biophysical Research Communications, 166, 860-866.
51. DOECKE, C. J., VERONESE, M. E., POND, S. M., MINERS, J. O., BIRKETT, D. J., SANSOM, L. N. and MCMANUS, M. E., 1991, Relationship between phenytoin and tolbutamide hydroxylations in human liver microsomes. British Journal of Clinical Pharmacology, 31, 125-130.
52. DRAPER, N. R. and SMITH, H., 1981, Applied Regression Analysis, 2nd edn (Chichester: John Wiley).
53. ECHIZEN, H., KAWASAKI, H., CHIBA, K., TANI, M. and ISHIZAKI, T., 1993, A potent inhibitory effect of erythromycin and other macrolide antibiotics on the mono-N-dealkylation metabolism of disopyramide with human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 264, 1425-1431.
54. ELLIS, S. W., CHING, M. S., WATSON, P. F., HENDERSON, C. J., SIMULA, A. P., LENNARD, M. S., TUCKER, G. T. and WOODS, H. F., 1992, Catalytic activities of human debrisoquine 4-hydroxylase cytochrome P450 (CYP2D6) expressed in yeast. Biochemical Pharmacology, 44, 617-620.
55. ELLIS, S. W., ROWLAND, K., HARLOW, J. R., SIMULA, A. P., LENNARD, M. S., WOODS, H. F., TUCKER, G. T. and WOLF, C. R., 1994, Regioselective and enantioselective metabolism of metoprolol by 2 human cDNA-derived CYP2D6 proteins. British Journal of Pharmacology, 112S, 244P.
56. EUGSTER, H. P., PROBST, M., WURGLER, F. E. and SENGSTAG, C., 1993, Caffeine, estradiol, and progesterone interact with human CYP1A1 and CYP1A2. Evidence from cDNA-directed expression in Saccharomyces cerevisiae. Drug Metabolism and Disposition, 21, 43-49.
57. EUGSTER, H. P., SENGSTAG, C., MEYER, U. A., HINNEN, A. and WURGLER, F. E., 1990, Constitutive and inducible expression of human cytochrome P450IA1 in yeast Saccharomyces cerevisiae: an alternative enzyme source for in vitro studies. Biochemical and Biophysical Research Communications, 172, 737-744.
58. FISHER, C. W., CAUDLE, D. L., MARTIN-WIXTROM, C., QUATTROCHI, L. C., TUKEY, R. H., WATERMAN, M. R. and ESTABROOK, R. W., 1992, High-level expression of functional human cytochrome P450 1A2 in Escherichia coli. FASEB Journal, 6, 759-764.
59. 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. and SKETT, P., 1992, Relative expression of cytochrome P450 isoenzymes in human liver and association with the metabolism of drugs and xenobiotics. Biochemical Journal, 281, 359-368.
60. FUHR, U., STROBL, G., MANAUT, F., ANDERS, E. M., SORGEL, F., LOPEZ-DE-BRINAS, E., CHU, D. T., PERNET, A. G., MAHR, G. and SANZ, F., 1993, Quinolone antibacterial agents: relationship between structure and in vitro inhibition of the human cytochrome P450 isoform CYP1A2. Molecular Pharmacology, 43, 191-199.
61. FURUYA, H., MEYER, U. A., GELBOIN, H. V. and GONZALEZ, F. J., 1991, Polymerase chain reaction-directed identification, cloning, and quantification of human CYP2C18 mRNA. Molecular Pharmacology, 40, 375-382.
62. GASCON, M. P. and DAYER, P., 1991, In vitro forecasting of drugs which may interfere with the biotransformation of midazolam. European Journal of Clinical Pharmacology, 41, 573-578.
63. GED, C., UMBENHAUER, D. R., BELLEVV, T. M., BORK, R. W., SRIVASTAVA, P. K., SHINRIKI, N., LLOYD, R. S. and GUENGERICH, F. P., 1988, Characterization of cDNAs, mRNAs, and proteins related to human liver microsomal cytochrome P-450 (S)-mephenytom 4′-hydroxylase. Biochemistry, 27, 6929-6940.
64. GILLAM, E. M. J., BABA, T., KIM, B. R., OHMORI, S. and GUENGERICH, F. P., 1993, Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Archives of Biochemistry and Biophysics, 305, 123-131.
65. GILLAM, E. M. J., GUO, Z. and GUENGERICH, F. P., 1994, Expression of modified human cytochrome P4502E1 in Escherichia coli, purification and spectral and catalytic properties. Archives of Biochemistry and Biophysics, 312, 59-66.
66. GILLAM, E. M. J., GUO, Z. Y., MARTIN, M. V., JENKINS, C. M. and GUENGERICH, F. P., 1995a, Expression of cytochrome-P450 2D6 in Escherichia coli, purification, and spectral and catalytic characterization. Archives of Biochemistry and Biophysics, 319, 540-550.
67. GILLAM, E. M. J., GUO, Z. Y., UENG, Y. F., YAMAZAKI, H., COCK, I., REILLY, P. E. B., HOOPER, W. D. and GUENGERICH, F. P., 1995b, Expression of cytochrome-P450-3A5 in Escherichia coli - effects of 5′ modification, purification, spectral characterization, reconstitution conditions, and catalytic activities. Archives of Biochemistry and Biophysics, 317, 374-384.
68. GOLDSTEIN, J. A., FALETTO, M. B., ROMKESSPARKS, M., SULLIVAN, T., KITAREEWAN, S., RAUCY, J. L., LASKER, J. M. and GHANAYEM, B. I., 1994, Evidence that CYP2C19 is the major (S)-mephenytoin 4′-hydroxylase in humans. Biochemistry, 33, 1743-1752.
69. GONZALEZ, F. J. and KORZEKWA, K. R., 1995. Cytochromes P450 expression systems. Annual Review of Pharmacology and Toxicology, 35, 369-390.
70. GONZALEZ, F. J., SCHMID, B. J., UMENO, M., MCBRIDE, O. W., HARDWICK, J. P., MEYER, U. A., GELBOIN, H. V. and IDLE, J. R., 1988, Human P450PCN1: sequence, chromosome localization, and direct evidence through cDNA expression that P450PCN1 is nifedipine. DNA, 7, 79-86.
71. GORSKL, J. C., HALL, S. D., VANDENBRANDEN, M., WRIGHTON, S. A. and JONES, D. R., 1994, Regioselective biotransformation of midazolam by memhers of the human cytochrome-P450-3A (CYP3A) subfamily. Biochemical Pharmacology, 47, 1643-1653.
72. GRANT, D. M., CAMPBELL, M. E., TANG, B. K. and KALOW, W., 1987, Biotransformation of caffeine by microsomes from human liver. Kinetic and inhibitor studies. Biochemical Pharmacology, 36, 1251-1260.
73. GUENGERICH, F. P., 1990, Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chemical Research in Toxicology, 3, 363-371.
74. GUENGERICH, F. P., 1992, Characterization of human cytochrome P450 enzymes. FASEB Journal, 6, 745-748.
75. GUENGERICH, F. P., 1995, Cytochromes P450 of human liver. Classification and activity profiles of the major enzymes. In G. M. Pacifici and G. N. Fracchia (eds), Advances in Drug Metabolism in Man (Luxembourg: European Commission), pp. 179-231.
76. GUENGERICH, F. P. and KIM, D. H., 1990, In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis, 11, 2275-2279.
77. GUENGERICH, F. P., KIM, D. H. and IWASAKI, M., 1991, Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chemical Research in Toxicology, 4, 168-179.
78. GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P. H., KREMERS, P., WOLFF, T. and WAXMAN, D. J., 1986a, Characterization of rat and human liver microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 261, 5051-5060.
79. GUENGERICH, F. P., MULLER-ENOCH, D, and BLAIR, I. A., 1986b, Oxidation of quinidine by human liver cytochrome P450. Molecular Pharmacology, 30, 287-295.
80. GUO, Z., GILLAM, E. M. J., OHMORI, S., TUKEY, R. H. and GUENGERICH, F. P., 1994, Expression of modified human cytochrome P4501A1 in Escherichia coli effects of 5′ substitution, stabilization, purification and catalytic properties. Archives of Biochemistry and Biophysics, 312, 436-446.
81. GUT, J., CATIN, T., DAYER, P., KRONBACH, T., ZANGER, U. and MEYER, U. A., 1986, Debrisoquine/sparteine-type polymorphism of drug oxidation: purification and characterization of two functionally different human liver cytochrome P450 isozymes involved in impaired hydroxylation of the prototype substrate bufuralol. Journal of Biological Chemistry, 261, 11734-11743.
82. HA, H. R., CHEN, J., LEUENBERGER, P. M., FREIBURGHAUS, A. U. and FOLLATH, F., 1995, In-vitro inhibition of midazolam and quinidine metabolism by flavonoids. European Journal of Clinical Pharmacology, 48, 367-371.
83. HALL, S. D., HAMMAN, M. A., RETTIE, A. E., WIENKERS, L. C., TRAGER, W. F., VANDENBRANDEN, M. and WRIGHTON, S. A., 1994, Relationships between the levels of cytochrome P4502C9 and its prototypic catalytic activities in human liver-microsomes. Drug Metabolism and Disposition, 22, 975-978.
84. HARRIS, J. W., KATKI, A., ANDERSON, L. W., CHMURNY, G. N., PAUKSTELIS, J. V., and COLLINS, J. M., 1994, Isolation, structural determination, and biological-activity of 6-alpha-hydroxytaxol, the principal human metabolite of taxol. Journal of Medicinal Chemistry, 37, 706-709.
85. HERMANS, J. J. and THIJSSEN, H. H., 1993, Human liver microsomal metabolism of the enantiomers of warfarin and acenocoumarol: P450 isozyme diversity determines the differences in their pharmacokinetics. British Journal of Pharmacology, 110, 482-490.
86. HEYN, H., STEVENS, J. C. and MARIETTA, M. P., 1995, The N-demethylation of S-mephenytoin by cytochromes P450-2B6 and -3A4. ISSX Proceedings, 8, 73.
87. IMAOKA, S., OGAWA, H., KIMURA, S. and GONZALEZ, F. J., 1993, Complete cDNA sequence and cDNA-directed expression of CYP4A11, a fatty acid omega-hydroxylase expressed in human kidney. DNA and Cell Biology, 12, 893-899.
88. INABA, T., JURIMA, M., MAHON, W. A. and KALOW, W. 1985, In vitro inhibition studies of two isozymes of human liver cytochrome P450: mephenytom p-hydroxylase and sparteine monooxygenase. Drug Metabolism and Disposition, 13, 443-448.
89. JONSSON, G., ASTROM, A. and ANDERSSON, P., 1995, Budesonide is metabolized by cytochrome-P450 3A (CYP3A) enzymes in human liver. Drug Metabolism and Disposition, 23, 137-142.
90. JURIMA-ROMET, M., CRAWFORD, K., CYR, T. and INABA, T., 1994, Terfenadine metabolism in human liver - in vitro inhibition by macrolide antibiotics and azole antifungals. Drug Metabolism and Disposition, 22, 849-857.
91. KAMINSKY, L. S., DE MORAIS, S. M., FALETTO, M. B., DUNBAR, D. A. and GOLDSTEIN, J. A., 1993, Correlation of human cytochrome P4502C substrate specificities with primary structure: warfarin as a probe. Molecular Pharmacology, 43, 234-239.
92. 2-terminal amino acid sequences of human and rat kidney fatty acid omega-hydroxylases. Biochimica et Biophysica Acta, 1123, 156-162.
93. 2+-chelate affinity purification, and characterization of solubility and aggregation. Archives of Biochemistry and Biophysics, 321, 277-288.
94. KERR, B. M., THUMMEL, K. E., WURDEN, C. J., KLEIN, S. M., KROETZ, D. L., GONZALEZ, F. J. and LEVY, R. H., 1994, Human liver carbamazepine metabolism - role of CYP3A4 and CYP2C8 in 10, 11-epoxide formation. Biochemical Pharmacology, 47, 1969-1979.
95. KERRY, N. L., SOMOGYI, A. A., BOCHNER, F. and MIKUS, G., 1994, The role of CYP2D6 in primary and secondary oxidative-metabolism of dextromethorphan - in-vitro studies using human liver-microsomes. British Journal of Clinical Pharmacology, 38, 243-248.
96. KHARASCH, E. D. and THUMMEL, K. E., 1993, Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Anesthesiology, 79, 795-807.
97. KOOP, D. R., LAETHEM, C. L. and TIERNEY, D. J., 1989, The utility of p-nitrophenol hydroxylation in P450IIE1 analysis. Drug Metabolism Reviews, 20, 541-551.
98. KRONBACH, T., 1991, Bufuralol, dextromethorphan, and debrisoquine as prototype substrates for human P450IID6. Methods in Enzymology, 206, 509-517.
99. KRONBACH, T., FISCHER, V. and MEYER, U. A. 1988, Cyclosporine metabolism in human liver: identification of a cytochrome P450III gene family as the major cyclosporine-metabolising enzyme explains interactions of cyclosporine with other drugs. Clinical Pharmacology and Therapeutics, 43, 630-635.
100. KRONBACH, T., MATHYS, D., UMENO, M., GONZALEZ, F. J. and MEYER, U. A., 1989, Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Molecular Pharmacology, 36, 89-96.
101. KRYNETSKI, E. Y., DRUTSA, V. L., KOVALEVA, I. E. and LUZIKOV, V. N., 1995, High-yield expression of functionally active human liver CYP2D6 in yeast-cells. Pharmacogenetics, 5, 103-109.
102. KUMAR, G. N., WALLE, U. K. and WALLE, T., 1994, Cytochrome-P450 3A-mediated human liver microsomal taxol 6-α-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 268, 1160-1165.
103. KUNZE, K. L. and TRAGER, W. F., 1993, Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chemical Research in Toxicology, 6, 649-656.
104. LABBE, G., DESCATOIRE, V., BEAUNE, P., LETTERON, P., LARREY, D. and PESSAYRE, D., 1989, Suicide inactivation of cytochrome P-450 by methoxsalen. Evidence for the covalent binding of a reactive intermediate to the protein moiety. Journal of Pharmacology and Experimental Therapeutics, 250, 1034-1042.
105. LANG, D. and BOCKER, R., 1995, Highly sensitive and specific high-performance liquid-chromatographic analysis of 7-hydroxywarfarin, a marker for human cytochrome P-4502C9 activity. Journal of Chromatography B-Biomedical Applications, 672, 305-309.
106. LEE, C. A., KADWELL, S. H., KOST, T. A. and SERABJITSINGH, C. J., 1995, CYP3A4 expressed by insect cells infected with a recombinant baculovirus containing both CYP3A4 and human NADPH-cytochrome P450 reductase is catalytically similar to human liver microsomal CYP3A4. Archives of Biochemistry and Biophysics, 319, 157-167.
107. LEEMANN, T., TRANSON, C. and DAYER, P., 1993, Cytochrome P450TB (CYP2C): a major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver. Life Sciences 52, 29-34.
108. LEO, M. A., LASKER, J. M., RAUCY, J. L., KIM, C. I., BLACK, M. and LIEBER, C. S., 1989, Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8. Archives of Biochemistry and Biophysics, 269, 305-312.
109. LOFT, S., OTTON, S. V., LENNARD, M. S., TUCKER, G. T. and POULSEN, H. E., 1991, Characterization of metronidazole metabolism by human liver microsomes. Biochemical Pharmacology, 41, 1127-1134.
110. LOPEZ GARCIA, M. P., DANSETTE, P. M., VALADON, P., AMAR, C., BEAUNE, P. H., GUENGERICH, F. P. and MANSUY, D., 1994, Human-liver cytochromes P-450 expressed in yeast as tools for reactive-metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P-450 2C9 and 2C10. European Journal of Biochemistry, 213, 223-232.
111. MADDEN, S., WOOLF, T. F., POOL, W. F. and PARK, B. K., 1993, An investigation into the formation of stable, protein-reactive and cytotoxic metabolites from tacrine in vitro. Studies with human and rat liver microsomes. Biochemical Pharmacology, 46, 13-20.
112. MASUBUCHI, Y., HOSOKAWA, S., HORIE, T., SUZUKI, T., OHMORI, S., KITADA, M. and NARIMATSU, S., 1994, Cytochrome-P450 isozymes involved in propranolol metabolism in human liver-microsomes - the role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metabolism and Disposition, 22, 909-915.
113. MAURICE, M., PICHARD, L., DAUJAT, M., FABRE, I., JOYEUX, H., DOMERGUE, J. and MAUREL, P., 1992, Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture. FASEB Journal, 6, 752-758.
114. MAYHEW, B. S., GORSKI, J. C. and HALL, S. D., 1995, Midazolam hydroxylation reveals the potential for non-hyperbolic kinetics in cytochrome P450 (CYP) 3A4. ISSX Proceedings, 8, 314.
115. 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.
116. MILES, J. S., MCLAREN, A. W., FORRESTER, L. M., GLANCEY, M. J., LANG, M. A. and WOLF, C. R., 1990, Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity. Biochemical Journal, 267, 365-371.
117. MIMURA, M., BABA, T., YAMAZAKI, H., OHMORI, S., INUI, Y., GONZALEZ, F. J., GUENGERICH, F. P. and SHIMADA, T., 1993, Characterization of cytochrome P-450 2B6 in human liver microsomes. Drug Metabolism and Disposition, 21, 1048-1056.
118. MINERS, J. O., REES, D. L. P., VALENTE, L., VERONESE, M. E. and BIRKETT, D. J., 1995, Human hepatic cytochrome-P450 2C9 catalyzes the rate-limiting pathway of torsemide metabolism. Journal of Pharmacology and Experimental Therapeutics, 272, 1076-1081.
119. MINERS, J. O., SMITH, K. J., ROBSON, R. A., MCMANUS, M. E., VERONESE, M. E. and BIRKETT, D. J., 1988, Tolbutamide hydroxylation by human liver microsomes: kinetic characterisation and relationship to other cytochrome P450 dependent xenobiotic oxidations. Biochemical Pharmacology, 37, 1137-1144.
120. MINISCALO, A., LUNDAHL, J., REGARDH, G., EDGAR, B. and ERIKSSON, U. G., 1992, Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavenoids found in grapefruit juice. Journal of Pharmacology and Experimental Therapeutics, 261, 1195-1199.
121. MOTULSKY, H. J. and RANSNAS, L. A., 1987, Fitting curves to data using nonlinear regression: a practical and nonmathematical review. FASEB Journal, 1, 365-374.
122. MURAKAMI, H., YABUSAKI, Y. and OHKAWA, H., 1986, Expression of rat NADPH-cytochrome P450 reductase in Saccharomyces cerevisiae. DNA and Cell Biology, 5, 1-10.
123. NEWTON, D.J., WANG, R. W. and LU, A. Y. H., 1995, Cytochrome-P450 inhibitors - evaluation of specificities in the in-vitro metabolism of therapeutic agents by human liver-microsomes. Drug Metabolism and Disposition, 23, 154-158.
124. OHGIYA, S., KOMORI, M., FUJITANI, T., MIURA, T., SHINRIKI, N. and KAMATAKI, T., 1989, Cloning of human cytochrome P-450 cDNA and its expression in Saccharomyces cerevisiae. Biochemistry International, 18, 429-438.
125. ONO, S., HATANAKA, T., HOTTA, H., TSUTSUI, M., SATOH, T. and GONZALEZ, F. J., 1995, Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics, 5, 143-150.
126. OTTON, S. V., CREWE, H. K., LENNARD, M. S., TUCKER, G. T. and WOODS, H. F., 1988, Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 247, 242-247.
127. PALMER, C. N., RICHARDSON, T. H., GRIFFIN, K. J., HSU, M. H., MUERHOFF, A. S., CLARK, J. E. and JOHNSON, E. F., 1993, Characterization of a cDNA encoding a human kidney, cytochrome P-450 4A fatty acid ω-hydroxylase and the cognate enzyme expressed in Escherichia coli. Biochimica et Biophysica Acta, 1172, 161-166.
128. PATTEN, C. J., ISHIZAKI, H., AOYAMA, T., LEE, M., NING, S. M., HUANG, W., GONZALEZ, F. J. and YANG, C. S., 1992, Catalytic properties of the human cytochrome P450 2E1 produced by cDNA expression in mammalian cells. Archives of Biochemistry and Biophysics, 299, 163-171.
129. PATTEN, C. J. and KOCH, P., 1995, Baculovirus expression of human P450 2E1 and cytochrome b(5)-spectral and catalytic properties and effect of b(5) on the stoichiometry of P450 2E1-catalyzed reactions. Archives of Biochemistry and Biophysics, 317, 504-513.
130. PATTEN, C. J., THOMAS, P. E., GUY, R. L., LEE, M., GONZALEZ, F. J., GUENGERICH, F. P. and YANG, C. S., 1993, Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chemical Research in Toxicology, 6, 511-518.
131. 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.
132. PEARSON, E. S. and HARTLEY, H. O., 1976, Biometrika Tables for Statisticians, vol. 1, 3rd edn (Cambridge: Cambridge University Press).
133. PELKONEN, O., SOTANIEMI, E. A. and AHOKAS, J. T., 1990, Coumarin 7-hydroxylase activity in human liver microsomes. Properties of the enzyme and interspecies comparison. British Journal of Clinical Pharmacology, 19, 59-66.
134. PENMAN, B. W., CHEN, L. P., GELBOIN, H. V., GONZALEZ, F. J. and CRESPI, C. L., 1994, Development of a human lymphoblastoid cell-line constitutively expressing human CYP1A1 cDNA - substrate-specificity with model substrates and promutagens. Carcinogenesis, 15, 1931-1937.
135. PENMAN, B. W., REECE, J., SMITH, T., YANG, C. S., GELBOIN, H. V., GONZALEZ, F. J. and CRESPI, C. L., 1993, Characterization of a human cell line expressing high levels of cDNA-derived CYP2D6. Pharmacogenetics, 3, 28-39.
136. PETER, R., BOCKER, 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-450IIE1. Chemical Research in Toxicology, 3, 566-573.
137. PEYRONNEAU, M. A., RENAUD, J. P., TRUAN, G., URBAN, P., POMPON, D. and MANSUY, D., 1992, Optimization of yeast-expressed human liver cytochrome P450 3A4 catalytic activities by coexpressing NADPH-cytochrome P450 reductase and cytochrome b5. European Journal of Biochemistry, 207, 109-116.
138. PICHARD, L., FABRE, I., FABRE, G., DOMERGUE, J., SAINT AUBERT, B., MOURAD, G. and MAUREL, P., 1990, Cyclosporin A drug interactions. Screening for inducers and inhibitors of cytochrome P-450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metabolism and Disposition, 18, 595-606.
139. PODOLL, T. D., KUNZE, K. L., THUMMEL, K. E., FISHER, J. M. and TRAGER, W. F., 1995, Evidence supporting mechanism-based inactivation of CYP3A by midazolam. ISSX Proceedings, 8, 154.
140. RAHMAN, A., KORZEKWA, K. R., GROGAN, J., GONZALEZ, F. J. and HARRIS, J. W., 1994, Selective biotransformation of taxol to 6-α-hydroxytaxol by human cytochrome-P450 2C8. Cancer Research, 54, 5543-5546.
141. RASMUSSEN, B. B., MAENPAA, J., PELKONEN, O., LOFT, S., POULSEN, H. E., LYKKESFELDT, J. and BROSEN, K., 1995, Selective serotonin reuptake inhibitors and theophylline metabolism in human liver-microsomes - potent inhibition by fluvoxamine. British Journal of Clinical Pharmacology, 39, 151-159.
142. 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.
143. RELLING, M. V., EVANS, W. E., FONNE-PFISTER, R. and MEYER, U. A., 1989, Anticancer drugs as inhibitors of two polymorphic cytochrome P450 enzymes, debrisoquine and mephenytoin hydroxylase, in human liver microsomes. Cancer Research, 49, 68-71.
144. REMMEL, R. P. and BURCHELL, B., 1993, Validation and use of cloned, expressed human drug-metabolizing enzymes in heterologous cells for analysis of drug metabolism and drug-drug interactions. Biochemical Pharmacology, 46, 559-566.
145. RENAUD, J. P., CULLIN, C., POMPON, D., BEAUNE, P. and MANSUY, D., 1990, Expression of human liver cytochrome P450 IIIA4 in yeast. A functional model for the hepatic enzyme. European Journal of Biochemistry, 194, 889-896.
146. 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 interactions. Chemical Research in Toxicology, 5, 54-59.
147. RETTIE, A. E., WIENKERS, L. C., GONZALEZ, F. J., TRAGER, W. F. and KORZEKWA, K. R., 1994, Impaired (S)-warfarin metabolism catalyzed by the R144C allelic variant of CYP2C9. Pharmacogenetics, 4, 39-42.
148. RICHARDSON, T. H., JUNG, F., GRIFFEN, K. J., WESTER, M., RAUCY, J. L., KEMPER, B., BORNHEIM, L. M., HASSETT, C., OMIECINSKI, C. J. and JOHNSON, E. F., 1995, A universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily in Escherichia coli. Archives of Biochemistry and Biophysics, 323, 87-96.
149. RODRIGUES, A. D., 1994, Use of in-vitro human metabolism studies in drug development - an industrial perspective. Biochemical Pharmacology, 48, 2147-2156.
150. RODRIGUES, A. D., KUKULKA, M. J., SURBER, B. W., THOMAS, S. B., UCHIC, J. T., ROTERT, G. A., MICHEL, G., THOMEKROMER, B. and MACHINIST, J. M., 1994, Measurement of liver microsomal cytochrome-P450 (CYP2D6) activity using [O-methyl-C-14] dextromethorphan. Analytical Biochemistry, 219, 309-320.
151. RODRIGUES, A. D., MULFORD, O. J., LEE, R. D., SURBER, B. W., KUKULKA, M. J., FERRERO, J. L., THOMAS, S. B., SHET, M. S. and ESTABROOK, R. W., 1995, In-vitro metabolism of terfenadine by a purified recombinant fusion protein containing cytochrome P4503A4 and NADPH-P450 reductase - comparison to human liver-microsomes and precision-cut liver-tissue slices. Drug Metabolism and Disposition, 23, 765-775.
152. ROMKES, M., FALETTO, M. B., BLAISDELL, J. A., RAUCY, J. L. and GOLDSTEIN, J. A., 1991, Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450IIC subfamily. Biochemistry, 30, 3247-3255.
153. RYAN, D. E. and LEVIN, W., 1990, Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacology and Therapeutics, 45, 153-239.
154. SANDHU, P., BABA, T. and GUENGERICH, F. P., 1993, Expression of modified cytochrome P450 2C10 (2C9) in Escherichia coli, purification, and reconstitution of catalytic activity. Archives of Biochemistry and Biophysics, 306, 443-450.
155. SANDHU, P., GUO, Z. Y., BABA, T., MARTIN, M. V., TUKEY, R. H. and GUENGERICH, F. P. 1994, Expression of modified human cytochrome-P450 1A2 in Escherichia coli - stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Archives of Biochemistry and Biophysics, 309, 168-177.
156. SARKAR, M., POLK, R. E., GUZELIAN, P. S., HUNT, C. and KARNES, H. T., 1990, In vitro effect of fluroquinolones on theophylline metabolism in human liver microsomes. Antimicrobial Agents and Chemotherapy, 34, 594-599.
157. SCHWEIKL, H., TAYLOR, J. A., KITAREEWAN, S., LINKO, P., NAGORNEY, D. and GOLDSTEIN, J. A., 1993, Expression of CYP1A1 and CYP1A2 genes in human liver. Pharmacogenetics, 3, 239-249.
158. SENGSTAG, C., EUGSTER, H. P. and WURGLER, F. E., 1994, High promutagen activating capacity of yeast microsomes containing human cytochrome P4501A and human NADPH-cytochrome P450 reductase. Carcinogenesis, 15, 837-844.
159. 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.
160. SESARDIC, D., BOOBIS, 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.
161. SHET, M. S., FISHER, C. W., HOLMANS, P. L. and ESTABROOK, R. W., 1993, Human cytochrome P450 3A4: enzymatic properties of a purified recombinant fusion protein containing NADPH-P450 reductase. Proceedings of the National Academy of Sciences, USA, 90, 11748-11752.
162. SHIMADA, T., MISONO, K. S. and GUENGERICH, F. P., 1986, Human liver microsomal cytochrome P450 mephenytom 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction. Journal of Biological Chemistry, 261, 909-921.
163. SHIMADA, T., YUN, C. H., YAMAZAKI, H., GAUTIER, J. C., BEAUNE, P. H. and GUENGERICH, F. P., 1992, Characterization of human lung microsomal cytochrome P-450 1A1 and its role in the oxidation of chemical carcinogens. Molecular Pharmacology, 41, 856-864.
164. 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.
165. SHOU, M., GROGAN, J., MANCEWICZ, J. A., KRAUSZ, K. W., GONZALEZ, F. J., GELBOIN, H. V. and KORZEKWA, K. R., 1994, Activation of CYP3A4 - evidence for the simultaneous binding of 2 substrates in a cytochrome-P450 active-site. Biochemistry, 33, 6450-6455.
166. SIESS, M. H., LECLERC, J., CANIVENCLAVIER, M. C., RAT, P. and SUSCHETET, M., 1995, Heterogeneous effects of natural flavonoids on monooxygenase activities in human and rat-liver microsomes. Toxicology and Applied Pharmacology, 130, 73-78.
167. SILVERS, K. J., CHAZINSKI, T., MCMANUS, M. E., BAUER, S. L., GONZALEZ, F. J., GELBOIN, H. V., MAUREL, P. and HOWARD, P. C., 1992, Cytochrome P-450 3A4 (nifedipine oxidase) is responsible for the C-oxidative metabolism of 1-nitropyrene in human liver microsomal samples. Cancer Research, 52, 6237-6243.
168. SKJELBO, E. and BROSEN, K., 1992, Inhibitors of imipramine metabolism by human liver microsomes. British Journal of Clinical Pharmacology, 34, 256-261.
169. SPALDIN, V., MADDEN, S., ADAMS, D. A., EDWARDS, R. J., DAVIES, D. S. and PARK, B. K., 1995, Determination of human hepatic cytochrome P4501A2 activity in-vitro - use of tacrine as an isoenzyme-specific probe. Drug Metabolism and Disposition, 23, 929-934.
170. SPALDIN, V., MADDEN, S., POOL, W. F., WOOLF, T. F. and PARK, B. K., 1994, The effect of enzyme inhibition on the metabolism and activation of tacrine by human liver microsomes. British Journal of Clinical Pharmacology, 38, 15-22.
171. SRIVASTAVA, P. K., YUN, C. H., BEAUNE, P. H., GED, C. and GUENGERICH, F. P., 1991, Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4′-hydroxylase cytochrome P-450 enzymes. Molecular Pharmacology, 40, 69-79.
172. STUPANS, I. and SANSOM, L. N., 1991, The inhibition of drug oxidation by anhydroerythromycin, an acid degradation product of erythromycin. Biochemical Pharmacology, 42, 2085-2090.
173. TASSANEEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., MCMANUS, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELBOIN, H. V. and MINERS, J. O., 1993a, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401-107.
174. TASSANEEYAKUL, W., MOHAMED, Z., BIRKETT, D. J., MCMANUS, M. E., VERONESE, M. E., TUKEY, R. H., QUATTROCHI, L. C., GONZALEZ, F. J. and MINERS, J. O., 1992, Caffeine as a probe for human cytochromes P450: validation using cDNA-expression, immunoinhibition and microsomal kinetic and inhibitor techniques. Pharmacogenetics, 2, 173-183.
175. TASSANEEYAKUL, W., VERONESE, M. E., BIRKETT, D. J., GONZALEZ, F. J. and MINERS, J. O., 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.
176. THUMMEL, K. E., KHARASCH, E. D., PODOLL, T. and KUNZE, K., 1993, Human liver microsomal enflurane defluorination catalyzed by cytochrome P-450 2E1. Drug Metabolism and Disposition, 21, 350-357.
177. TINEL, M., BELGHITI, J., DESCATOIRE, V., AMOUYAL, G., LETTERON, P., GENEVE, J., LARREY, D. and PESSAYRE, D., 1987, Inactivation of human liver cytochrome P450 by the drug methoxsalen and other psoralen derivatives. Biochemical Pharmacology, 36, 951-955.
178. TRACY, T. S., ROSENBLUTH, B. W., WRIGHTON, S. A., GONZALEZ, F. J. and KORZEKWA, K. R., 1995, Role of cytochrome-P450 2C9 and an allelic variant in the 4′-hydroxylation of (r)-flurbiprofen and (s)-flurbiprofen. Biochemical Pharmacology, 4, 1269-1275.
179. TYNDALE, R., AOYAMA, T., BROLY, F., MATSUNAGA, T., INABA, T., KALOW, W., GELBOIN, H. V., MEYER, U. A. and GONZALEZ, F. J., 1991, Identification of a new variant CYP2D6 allele lacking the codon encoding Lys-281: possible association with the poor metabolizer phenotype. Pharmacogenetics, 1, 26-32.
180. URBAN, P., TRUAN, G., GAUTIER, J. C. and POMPON, D., 1993, Xenobiotic metabolism in humanized yeast : engineered yeast cells producing human NADPH-cytochrome P450 reductase, cytochrome b5, epoxide hydrolase and P450s. Biochemical Society Transactions, 21, 1028-1034.
181. VALERO, F., DE LA TORRE, R., BOOBIS, A. R., MURRAY, S. and SEGURA, J., 1990, Assay of caffeine metabolism in vitro by human liver microsomes using radio-high-performance liquid chromatography. Journal of Pharmacology and Biomedical Analysis, 8, 783-787.
182. VERONESE, M. E., DOECKE, C. J., MACKENZIE, P. I., MCMANUS, M. E., MINERS, J. O., REES, D. L., GASSER, R., MEYER, U. A. and BIRKETT, D. J., 1993, Site-directed mutation studies of human liver cytochrome P-450 isoenzymes in the CYP2C subfamily. Biochemical Journal, 289, 533-538.
183. VERONESE, M. E., MACKENZIE, P. I., DOECKE, C. J., MCMANUS, M. E., MINERS, J. O. and BIRKETT, D. J., 1991, Tolbutamide and phenytoin hydroxylations by cDNA-expressed human liver cytochrome P4502C9. Biochemical and Biophysical Research Communications, 175, 1112-1118.
184. VONMOLTKE, L. L., GREENBLATT, D. J., COURT, M. H., DUAN, S. X., HARMATZ, J. S. and SHADER, R. I., 1995, Inhibition of alprazolam and desipramine hydroxylation in-vitro by paroxetine and fluvoxamine - comparison with other selective serotonin reuptake inhibitor antidepressants. Journal of Clinical Psychopharmacology, 15, 125-131.
185. WATERMAN, M. R. and HILDEBRAND, M., 1994, Assessment of the Use of Single Cytochrome P450 Enzymes in Drug Research, (Bohn: Springer).
186. 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 P450 in human liver. Proceedings of the National Academy of Sciences, USA, 82, 6310-6314.
187. WAXMAN, D. J., LAPENSON, D. P., AOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J. and KORZEKWA, K., 1991, Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Archives of Biochemistry and Biophysics, 290, 160-166.
188. WEAVER, R. J., DICKINS, M. and BURKE, M. D., 1993, Cytochrome P450 2C9 is responsible for hydroxylation of the naphthoquinone antimalarial drug 58C80 in human liver. Biochemical Pharmacology, 46, 1183-1197.
189. WEISBERG, S., 1980, Applied Linear Regression (Chichester: John Wiley).
190. WINTERS, D. K. and CEDERBAUM, A. I., 1992, Expression of a catalytically active human cytochrome P-4502E1 in Escherichia coli. Biochimica et Biophysica Acta, 1156, 43-49.
191. WRIGHT, J. D., HELSBY, N. A. and WARD, S. A., 1995, The role of S-mephenytoin hydroxylase (CYP2C19) in the metabolism of the antimalarial biguanides. British Journal of Clinical Pharmacology, 39, 441-444.
192. WRIGHTON, S. A., THOMAS, P. E., RYAN, D. E. and LEVIN, W., 1987, Purification and characterization of ethanol-inducible human hepatic cytochrome P450HLj. Archives of Biochemistry and Biophysics, 258, 292-297.
193. WRIGHTON, S. A., BRIAN, W. R., SARI, M. A., IWASAKI, M., GUENGERICH, F. P., RAUCY, J. L., MOLOWA, D. T. and VANDENBRANDEN, M., 1990, Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Molecular Pharmacology, 38, 207-213.
194. WRIGHTON, S. A., RING, B. J., WATKINS, P. B. and VANDENBRANDEN, M., 1989, Identification of a polymorphically expressed member of the human cytochrome P-450III family. Molecular Pharmacology, 36, 97-105.
195. WRIGHTON, S. A., STEVENS, J. C., BECKER, G. W. and VANDENBRANDEN, M., 1993, Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin 4′-hydroxylation. Archives of Biochemistry and Biophysics, 306, 240-245.
196. WRIGHTON, S. A. and VANDENBRANDEN, M., 1989, Isolation and characterization of human fetal liver cytochrome P450HLp2: a third member of the P450III gene family. Archives of Biochemistry and Biophysics, 268, 144-151.
197. YAMANO, S., NHAMBURO, P. T., AOYAMA, T., MEYER, U. A., INABA, T., KALOW, W., GELBOIN, H. V., MCBRIDE, O. W. and GONZALEZ, F. J., 1989, 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.
198. YAMANO, S., TATSUNO, J. and GONZALEZ, F. J., 1990, The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry, 29, 1322-1329.
199. YAMAZAKI, H., GUO, Z. Y. and GUENGERICH, F. P., 1995, Selectivity of cytochrome P4502E1 in chlorzoxazone 6-hydroxylation. Drug Metabolism and Disposition, 23, 438-440.
200. YAMAZAI, H., GUO, Z. Y., PERSMARK, M., MIMURA, M., INOUE, K., GUENGERICH, F. P. and SHIMADA, T., 1994a, Bufuralol hydroxylation by cytochrome-P450 2D6 and 1A2 enzymes in human liver-microsomes. Molecular Pharmacology, 46, 568-577.
201. YAMAZAKI, H., INUI, Y., YUN, C. H., GUENGERICH, F. P. and SHIMADA, T., 1992, Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 13, 1789-1794.
202. YAMAZAKI, H., MIMURA, M., SUGAHARA, C. and SHIMADA, T., 1994b, Catalytic roles of rat and human cytochrome-P450-2A enzymes in testosterone 7-α-hydroxylation and coumarin 7-hydroxylation. Biochemical Pharmacology, 48, 1524-1527.
203. m diazepam N-demethylase in livers of poor metabolizers for S-mephenytoin 4′-hydroxylation. Pharmacogenetics, 4, 323-331.
204. YASUMORI, T., MURAYAMA, N., YAMAZOE, Y., ABE, A., NOGI, Y., FUKASAWA, T. and KATO, R., 1989, Expression of a human P-450IIC gene in yeast cells using galactose-inducible expression system. Molecular Pharmacology, 35, 443-449.
205. YOO, J. S., GUENGERICH, F. P. and YANG, C. S., 1988, Metabolism of N-nitrosodialkylamines by human liver microsomes. Cancer Research, 48, 1499-1504.
206. YOO, J. S., ISHIZAKI, H. and YANG, C. S., 1991, Enzyme kinetics of N-nitrosodimethylamine demethylase in rodents and humans. IARC Science Publications, 366-369.
207. YOSHIMOTO, K., ECHIZEN, H., CHIBA, K., TANI, M. and ISHIZAKI, T., 1995, Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers - N-desisopropylation is mediated mainly by CYP1A2. British Journal of Clinical Pharmacology, 39, 421-431.
208. YUN, C. H., SHIMADA, T. and GUENGERICH, F. P., 1991, Purification and characterization of human liver microsomal cytochrome P-450 2A6. Molecular Pharmacology, 40, 679-685.
209. YUN, C. H., OKERHOLM, R. A. and GUENGERICH, F. P., 1993, Oxidation of the antihistaminic drug terfenadine m human liver microsomes. Role of cytochrome P-450 3A(4) in N-dealkylation and C-hydroxylation. Drug Metabolism and Disposition, 21, 403-409.
210. YUN, C. H., WOOD, M., WOOD, A. J. and GUENGERICH, F. P., 1992, Identification of the pharmacogenetic determinants of alfentanil metabolism: cytochrome P-450 3A4. An explanation of the variable elimination clearance. Anesthesiology, 77, 467-474.
211. ZANGER, U. M., VILBOIS, F., HARDWICK, J. P. and MEYER, U. A., 1988, Absence of hepatic cytochrome P450bufI causes genetically deficient debrisoquine oxidation in man. Biochemistry, 27, 5447-5454.
212. ZELDIN, D. C., DUBOIS, R. N., FALCK, J. R. and CAPDEVILA, J. H., 1995, Molecular-cloning, expression and characterization of an endogenous human cytochrome-P450 arachidonic-acid epoxygenase isoform. Archives of Biochemistry and Biophysics, 322, 76-86.
213. ZHOU, X. J., ZHOU-PAN, X. R., GAUTHIER, T., PLACIDI, M., MAUREL, P. and RAHMANI, R., 1993, Human liver microsomal cytochrome P450 3A isozymes mediated vindesine biotransformation. Metabolic drug interactions. Biochemical Pharmacology, 45, 853-861.