Predicting drug clearance from recombinantly expressed CYPs: Intersystem extrapolation factors

Xenobiotica

Volumn 34, Issue 2, 2004, Pages 151-178

  Proctor, N J ^a   Tucker, G T ^a   Rostami Hodjegan, A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; AMIODARONE; BUFURALOL; BUPRENORPHINE; CAFFEINE; COUMARIN; CYCLOSPORIN A; CYTOCHROME P450; DEBRISOQUINE; DEXTROMETHORPHAN; DIAZEPAM; DICLOFENAC; DILTIAZEM; ERYTHROMYCIN; ETOPOSIDE; FELODIPINE; IBUPROFEN; IMIPRAMINE; LAURIC ACID; LORNOXICAM; MELATONIN; MEXILETINE; MIDAZOLAM; NAPROXEN; NIFEDIPINE; OMEPRAZOLE; PACLITAXEL; PHENACETIN; RECOMBINANT ENZYME; UNINDEXED DRUG;

ACCURACY; ARTICLE; COVARIANCE; DATA BASE; DRUG CLEARANCE; DRUG METABOLISM; ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; EXPERIMENTAL DESIGN; GENE EXPRESSION SYSTEM; GENETIC RECOMBINATION; GENETIC VARIABILITY; IN VITRO STUDY; IN VIVO STUDY; PREDICTION; PROTEIN EXPRESSION; STATISTICAL MODEL; VARIANCE;

ALGORITHMS; CYTOCHROME P-450 ENZYME SYSTEM; DATABASES, GENETIC; HUMANS; ISOENZYMES; KINETICS; MODELS, STATISTICAL; PHARMACEUTICAL PREPARATIONS; PREDICTIVE VALUE OF TESTS; RECOMBINANT PROTEINS;

EID: 1542344547     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/00498250310001646353     Document Type: Article

References (132)

1. ABDEL-RAHMAN, S. M., MARCUCCI, K., BOGE, T., GOTSCHALL, R. R., KEARNS, G. L. and LEEDER, J. S., 1999, Potent inhibition of cytochrome P-450 2D6-mediated dextromethorphan O-demethylation by terbinafine. Drug Metabolism and Disposition, 27, 770-775.
2. ABELO, A., ANDERSSON, T. B., BREDBERG, U., SKANBERG, I. and WEIDOLF, L., 2000, Stereoselective metabolism by human liver CYP enzymes of a substituted benzimidazole. Drug Metabolism and Disposition, 28, 58-64.
3. AMET, Y., BERTHOU, F., BAIRD, S., DREANO, Y., BAIL, J. P. and MENEZ, J. F., 1995, Validation of the (omega-1)-hydroxylation of lauric acid as an in vitro substrate probe for human liver CYP2E1. Biochemical Pharmacology, 50, 1775-1782.
4. BACK, D. J. and TJIA, J. F., 1991, Comparative effects of the antimycotic drugs ketoconazole, fluconazole, itraconazole and terbinafine on the metabolism of cyclosporin by human liver microsomes. British Journal of Clinical Pharmacology, 32, 624-626.
5. BACKMAN, J. T., KYRKLUND, C., KIVISTO, K. T., WANG, J. S. and NEUVONEN, P. J., 2000, Plasma concentrations of active simvastatin acid are increased by gemfibrozil. Clinical Pharmacology and Therapeutics, 68, 122-129.
6. BECQUEMONT, L., LE BOT, M. A., RICHE, C., FUNCK-BRENTANO, C., JAILLON, P. and BEAUNE, P., 1998, Use of heterologously expressed human cytochrome P450 1A2 to predict tacrine-fluvoxamine drug interaction in man. Pharmacogenetics, 8, 101-108.
7. BECQUEMONT, L., MOUAJJAH, S., ESCAFFRE, O., BEAUNE, P., FUNCK-BRENTANO, C. and JAILLON, P., 1999, Cytochrome P-450 3A4 and 2C8 are involved in zopiclone metabolism. Drug Metabolism and Disposition, 27, 1068-1073.
8. BELLE, D. J., CALLAGHAN, J. T., GORSKI, J. C., MAYA, J. F., MOUSA, O., WRIGHTON, S. A. and HALL, S. D., 2002, The effects of an oral contraceptive containing ethinyloestradiol and norgestrel on CYP3A activity. British Journal of Clinical Pharmacology, 53, 67-74.
9. BELPAIRE, F. M., WIJNANT, P., TEMMERMAN, A., RASMUSSEN, B. B. and BROSEN, K., 1998, The oxidative metabolism of metoprolol in human liver microsomes: inhibition by the selective serotonin reuptake inhibitors. European Journal of Clinical Pharmacology, 54, 261-264.
10. BONNABRY, P., LEEMANN, T. and DAYER, P., 1996, Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. European Journal of Clinical Pharmacology, 49, 305-308.
11. BOOBIS, A. R., MCKILLOP, D., ROBINSON, D. T., ADAMS, D. A. and MCCORMICK, D. J., 1998, Interlaboratory comparison of the assessment of P450 activities in human hepatic microsomal samples. Xenobiotica, 28, 493-506.
12. BROLY, F., LIBERSA, C., LHERMITTE, M., BECHTEL, P. and DUPUIS, B., 1989, Effect of quinidine on the dextromethorphan O-demethylase activity of microsomal fractions from human liver. British Journal of Clinical Pharmacology, 28, 29-36.
13. m. British Journal of Clinical Pharmacology, 45, 512P-513P.
14. CHAURET, N., GAUTHIER, A. and NICOLL-GRIFFITH, D. A., 1998, Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes. Drug Metabolism and Disposition, 26, 1-4.
15. CHIBA, K., KOBAYASHI, K., MANABE, K., TANI, M., KAMATAKI, T. and ISHIZAKI, T., 1993, Oxidative metabolism of omeprazole in human liver microsomes: cosegregation with S-mephenytoin 4′-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 266, 52-59.
16. CHING, M. S., BLAKE, C. L., MALEK, N. A., ANGUS, P. W. and GHABRIAL, H., 2001, Differential inhibition of human CYP1A1 and CYP1A2 by quinidine and quinine. Xenobiotica, 31, 757-767.
17. CLARKE, S. E., BALDWIN, S. J., BLOOMER, J. C., AYRTON, A. D., SOZIO, R. S. and CHENERY, R. J., 1994, 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.
18. COLLER, J. K., SOMOGYI, A. A. and BOCHNER, F., 1999, Comparison of (S)-mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms. British Journal of Clinical Pharmacology, 48, 158-167.
19. COURT, M. H., VON MOLTKE, L. L., SHADER, R. I. and GREENBLATT, D. J., 1997, Biotransformation of chlorzoxazone by hepatic microsomes from humans and ten other mammalian species. Biopharmaceutics and Drug Disposition, 18, 213-226.
20. CRESPI, C. L., 1995, Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research. Advances in Drug Research, 26, 179-235.
21. 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.
22. 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.
23. DRAPER, A. J., MADAN, A., SMITH, K. and PARKINSON, A., 1998, Development of a non-high pressure liquid chromatography assay to determine testosterone hydroxylase (CYP3A) activity in human liver microsomes. Drug Metabolism and Disposition, 26, 299-304.
24. EAGLING, V. A., TJIA, J. F. and BACK, D. J., 1998, Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. British Journal of Clinical Pharmacology, 45, 107-114.
25. ELLIS, S. W., ROWLAND, K., ACKLAND, M. J., REKKA, E., SIMULA, A. P., LENNARD, M. S., WOLF, C. R. and TUCKER, G. T., 1996, Influence of amino acid residue 374 of cytochrome P-450 2D6 (CYP2D6) on the regio- and enantio-selective metabolism of metoprolol. Biochemical Journal, 316, 647-654.
26. ERIKSSON, U. G., LUNDAHL, J., BAARNHIELM, C. and REGARDH, C. G., 1991, Stereoselective metabolism of felodipine in liver microsomes from rat, dog, and human. Drug Metabolism and Disposition, 19, 889-894.
27. 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.
28. FACCIOLA, G., HIDESTRAND, M., VON BAHR, C. and TYBRING, G., 2001, Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. European Journal of Clinical Pharmacology, 56, 881-888.
29. 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.
30. GORSKI, J. C., JONES, D. R., WRIGHTON, S. A. and HALL, S. D., 1994, Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily. Biochemical Pharmacology, 48, 173-182.
31. GRANVIL, C. P., KRAUSZ, K. W., GELBOIN, H. V., IDLE, J. R. and GONZALEZ, F. J., 2002, 4-Hydroxylation of debrisoquine by human CYP1A1 and its inhibition by quinidine and quinine. Journal of Pharmacology and Experimental Therapeutics, 301, 1025-1032.
32. HA, H. R., CHEN, J., KRAHENBUHL, S. and FOLLATH, F., 1996, Biotransformation of caffeine by cDNA-expressed human cytochromes P-450. European Journal of Clinical Pharmacology, 49, 309-315.
33. HALLIDAY, R. C., JONES, B. C., SMITH, D. A., KITTERINGHAM, N. R. and PARK, B. K., 1995, An investigation of the interaction between halofantrine, CYP2D6 and CYP3A4: studies with human liver microsomes and heterologous enzyme expression systems. British Journal of Clinical Pharmacology, 40, 369-378.
34. HAMAOKA, N., ODA, Y., HASE, I. and ASADA, A., 2001, Cytochrome P4502B6 and 2C9 do not metabolize midazolam: kinetic analysis and inhibition study with monoclonal antibodies. British Journal of Anaesthesia, 86, 540-544.
35. HARRIS, J. W., RAHMAN, A., KIM, B. R., GUENGERICH, F. P. and COLLINS, J. M., 1994, Metabolism of taxol by human hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Research, 54, 4026-4035.
36. HEMERYCK, A., DE VRIENDT, C. and BELPAIRE, F. M., 1999, Inhibition of CYP2C9 by selective serotonin reuptake inhibitors: in vitro studies with tolbutamide and (S)-warfarin using human liver microsomes. European Journal of Clinical Pharmacology, 54, 947-951.
37. HICKMAN, D., WANG, J. P., WANG, Y. and UNADKAT, J. D., 1998, Evaluation of the selectivity of In vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metabolism and Disposition, 26, 207-215.
38. HOUSTON, J. B. and CARLILE, D. J., 1997, Prediction of hepatic clearance from microsomes, hepatocytes, and liver slices. Drug Metabolism Reviews, 29, 891-922.
39. IEIRI, I., TAINAKA, H., MORITA, T., HADAMA, A., MAMIYA, K., HAYASHIBARA, M., NINOMIYA, H., OHMORI, S., KITADA, M., TASHIRO, N., HIGUCHI, S. and OTSUBO, K., 2000, Catalytic activity of three variants (Ile, Leu, and Thr) at amino acid residue 359 in human CYP2C9 gene and simultaneous detection using single-strand conformation polymorphism analysis. Therapeutic Drug Monitoring, 22, 237-244.
40. INTERNATIONAL COMMISSION ON RADIOLOGICAL PROTECTION, TASK GROUP ON REFERENCE MAN, 1975, Report of the Task Group on Reference Man: A Report (Oxford: Pergamon).
41. IWATA, H., FUJITA, K., KUSHIDA, H., SUZUKI, A., KONNO, Y., NAKAMURA, K., FUJINO, A. and KAMATAKI, T., 1998, High catalytic activity of human cytochrome P450 co-expressed with human NADPH-cytochrome P450 reductase in Escherichia coli. Biochemical Pharmacology, 55, 1315-1325.
42. IWATSUBO, T., HIROTA, N., OOIE, T., SUZUKI, H., SHIMADA, N., CHIBA, K., ISHIZAKI, T., GREEN, C. E., TYSON, C. A. and SUGIYAMA, Y., 1997, Prediction of in vivo drug metabolism in the human liver from in vitro metabolism data. Pharmacology and Therapeutics, 73, 147-171.
43. JACQZ-AIGRAIN, E., FUNCK-BRENTANO, C. and CRESTEIL, T., 1993, CYP2D6- and CYP3A-dependent metabolism of dextromethorphan in humans. Pharmacogenetics, 3, 197-204.
44. JONES, B. C., HYLAND, R., ACKLAND, M., TYMAN, C. A. and SMITH, D. A., 1998, Interaction of terfenadine and its primary metabolites with cytochrome P450 2D6. Drug Metabolism and Disposition, 26, 875-882.
45. JONES, D. R., GORSKI, J. C., HAMMAN, M. A., MAYHEW, B. S., RIDER, S. and HALL, S. D., 1999, Diltiazem inhibition of cytochrome P-450 3A activity is due to metabolite intermediate complex formation. Journal of Pharmacology and Experimental Therapeutics, 290, 1116-1125.
46. KAHN, G. C., BOOBIS, A. R., MURRAY, S., BRODIE, M. J. and DAVIES, D. S., 1982, Assay and characterisation of debrisoquine 4-hydroxylase activity of microsomal fractions of human liver. British Journal of Clinical Pharmacology, 13, 637-645.
47. KANAMITSU, S., ITO, K., GREEN, C. E., TYSON, C. A., SHIMADA, N. and SUGIYAMA, Y., 2000, Prediction of in vivo interaction between triazolam and erythromycin based on in vitro studies using human liver microsomes and recombinant human CYP3A4. Pharmaceutical Research, 17, 419-426.
48. KATOH, M., NAKAJIMA, M., SHIMADA, N., YAMAZAKI, H. and YOKOI, T., 2000, Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. European Journal of Clinical Pharmacology, 55, 843-852.
49. KAWASHIRO, T., YAMASHITA, K., ZHAO, X. J., KOYAMA, E., TANI, M., CHIBA, K. and ISHIZAKI, T., 1998, A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 286, 1294-1300.
50. 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.
51. KOBAYASHI, K., NAKAJIMA, M., CHIBA, K., YAMAMOTO, T., TANI, M., ISHIZAKI, T. and KUROIWA, Y., 1998, Inhibitory effects of antiarrhythmic drugs on phenacetin O-deethylation catalysed by human CYP1A2. British Journal of Clinical Pharmacology, 45, 361-368.
52. KOBAYASHI, K., NAKAJIMA, M., OSHIMA, K., SHIMADA, N., YOKOI, T. and CHIBA, K., 1999, Involvement of CYP2E1 as A low-affinity enzyme in phenacetin O-deethylation in human liver microsomes. Drug Metabolism and Disposition, 27, 860-865.
53. KUMAR, G. N., WALLE, U. K. and WALLE, T., 1994, Cytochrome P450 3A-mediated human liver microsomal taxol 6 alpha-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 268, 1160-1165.
54. KUNZE, K. L., WIENKERS, L. C., THUMMEL, K. E. and TRAGER, W. F., 1996, Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metabolism and Disposition, 24, 414-421.
55. LABEDZKI, A., BUTERS, J., JABRANE, W. and FUHR, U., 2002, Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2. Biochemical Pharmacology, 63, 2159-2167.
56. LASKER, J. M., WESTER, M. R., ARAMSOMBATDEE, E. and RAUCY, J. L., 1998, Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Archives of Biochemistry and Biophysics, 353, 16-28.
57. LAVE, T., COASSOLO, P. and REIGNER, B., 1999, Prediction of hepatic metabolic clearance based on interspecies allometric scaling techniques and in vitro-in vivo correlations. Clinical Pharmacokinetics, 36, 211-231.
58. LEE, C. A., KADWELL, S. H., KOST, T. A. and SERABJIT-SINGH, 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.
59. 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.
60. LIGHTFOOT, T., ELLIS, S. W., MAHLING, J., ACKLAND, M. J., BLANEY, F. E., BIJLOO, G. J., DE GROOT, M. J., VERMEULEN, N. P., BLACKBURN, G. M., LENNARD, M. S. and TUCKER, G. T., 2000, Regioselective hydroxylation of debrisoquine by cytochrome P4502D6: implications for active site modelling. Xenobiotica, 30, 219-233.
61. LUCAS, D., FERRARA, R., GONZALEZ, E., BODENEZ, P., ALBORES, A., MANNO, M. and BERTHOU, F., 1999, Chlorzoxazone, a selective probe for phenotyping CYP2E1 in humans. Pharmacogenetics, 9, 377-388.
62. MADAN, A., USUKI, E., BURTON, L. A., OGILVIE, B. W. and PARKINSON, A., 2002, In vitro approaches for studying the inhibition of drug-metabolizing enzymes and identifying the drug-metabolizing enzymes responsible for the metabolism of drugs. In Rodrigues A. D. (ed.), Drug-Drug Interactions (New York: Marcel Dekker).
63. MADANI, S., PAINE, M. F., LEWIS, L., THUMMEL, K. E. and SHEN, D. D., 1999, Comparison of CYP2D6 content and metoprolol oxidation between microsomes isolated from human livers and small intestines. Pharmaceutical Research, 16, 1199-1205.
64. MAENPAA, J., HALL, S. D., RING, B. J., STROM, S. C. and WRIGHTON, S. A., 1998, Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics, 8, 137-155.
65. MANCY, A., ANTIGNAC, M., MINOLETTI, C., DIJOLS, S., MOURIES, V., DUONG, N. T., BATTIONI, P., DANSETTE, P. M. and MANSUY, D., 1999, Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry, 38, 14264-14270.
66. MANKOWSKI, D. C., LAWTON, M. P. and EKINS, S., 2000, Characterization of transgenic mouse strains using six human hepatic cytochrome P450 probe substrates. Xenobiotica, 30, 745-754.
67. MARTINEZ, C., GERVASINI, G., AGUNDEZ, J. A., CARRILLO, J. A., RAMOS, S. I., GARCIA-GAMITO, F. J., GALLARDO, L. and BENITEZ, J., 2000, Modulation of midazolam 1-hydroxylation activity in vitro by neurotransmitters and precursors. European Journal of Clinical Pharmacology, 56, 145-151.
68. MASIMIREMBWA, C. M., OTTER, C., BERG, M., JONSSON, M., LEIDVIK, B., JONSSON, E., JOHANSSON, T., BACKMAN, A., EDLUND, A. and ANDERSSON, T. B., 1999, Heterologous expression and kinetic characterization of human cytochromes P-450: validation of a pharmaceutical tool for drug metabolism research. Drug Metabolism and Disposition, 27, 1117-1122.
69. MAUTZ, D. S., SHEN, D. D. and NELSON, W. L., 1995, Regioselectivity and enantioselectivity of metoprolol oxidation by two variants of cDNA-expressed P4502D6. Pharmaceutical Research, 12, 2053-2056.
70. MCGINNITY, D. F., GRIFFIN, S. J., MOODY, G. C., VOICE, M., HANLON, S., FRIEDBERG, T. and RILEY, R. J., 1999, Rapid characterization of the major drug-metabolizing human hepatic cytochrome P-450 enzymes expressed in Escherichia coli. Drug Metabolism and Disposition, 27, 1017-1023.
71. MINDER, E. I., MEIER, P. J., MULLER, H. K., MINDER, C. and MEYER, U. A., 1984, Bufuralol metabolism in human liver: a sensitive probe for the debrisoquine-type polymorphism of drug oxidation. European Journal of Clinical Investigation, 14, 184-189.
72. 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 P-450 dependent xenobiotic oxidations. Biochemical Pharmacology, 37, 1137-1144.
73. NADIN, L. and MURRAY, M., 1999, Participation of CYP2C8 in retinoic acid 4-hydroxylation in human hepatic microsomes - structure, mechanism and biochemistry. Biochemical Pharmacology, 58, 1201-1208.
74. 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.
75. NAKAJIMA, M., NAKAMURA, S., TOKUDOME, S., SHIMADA, N., YAMAZAKI, H. and YOKOI, T., 1999, Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metabolism and Disposition, 27, 1381-1391.
76. NAKAJIMA, M., TANE, K., NAKAMURA, S., SHIMADA, N., YAMAZAKI, H. and YOKOI, T., 2002, Evaluation of approach to predict the contribution of multiple cytochrome P450s in drug metabolism using relative activity factor: effects of the differences in expression levels of NADPH-cytochrome P450 reductase and cytochrome b(5) in the expression system and the differences in the marker activities. Journal of Pharmaceutical Sciences, 91, 952-963.
77. NAKAMURA, K., ARIYOSHI, N., YOKOI, T., OHGIYA, S., CHIDA, M., NAGASHIMA, K., INOUE, K., KODAMA, T., SHIMADA, N. and KAMATAKI, T., 2002, CYP2D6. 10 present in human liver microsomes shows low catalytic activity and thermal stability. Biochemical and Biophysical Research Communications, 293, 969-973.
78. NELSON, M. H., BIRNBAUM, A. K. and REMMEL, R. P., 2001, Inhibition of phenytoin hydroxylation in human liver microsomes by several selective serotonin re-uptake inhibitors. Epilepsy Research, 44, 71-82.
79. OBACH, R. S., 1999, Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metabolism and Disposition, 27, 1350-1359.
80. OHYAMA, K., NAKAJIMA, M., NAKAMURA, S., SHIMADA, N., YAMAZAKI, H. and YOKOI, T., 2000, A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metabolism and Disposition, 28, 1303-1310.
81. PARIKH, A., JOSEPHY, P. D. and GUENGERICH, F. P., 1999, Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties. Biochemistry, 38 5283-5289.
82. 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.
83. PRITCHARD, M. P., GLANCEY, M. J., BLAKE, J. A., GILHAM, D. E., BURCHELL, B., WOLF, C. R. and FRIEDBERG, T., 1998, Functional co-expression of CYP2D6 and human NADPH-cytochrome P450 reductase in Escherichia coli. Pharmacogenetics, 8, 33-42.
84. PROCTOR, N. J., ROSTAMI-HODJEGAN, A. and TUCKER, G. T., 2003, In vitro prediction of population in vivo drug clearance using updated scaling factors. British Journal of Clinical Pharmacology, 55, 445.
85. PRUEKSARITANONT, T., GORHAM, L. M., MA, B., LIU, L., YU, X., ZHAO, J. J., SLAUGHTER, D. E., ARISON, B. H. and VYAS, K. P., 1997, In vitro metabolism of simvastatin in humans [SBT]identification of metabolizing enzymes and effect of the drug on hepatic P450s. Drug Metabolism and Disposition, 25, 1191-1199.
86. PURBA, H. S., BACK, D. J. and ORME, M. L., 1987, Tolbutamide 4-hydroxylase activity of human liver microsomes: effect of inhibitors. British Journal of Clinical Pharmacology, 24, 230-234.
87. RAHMAN, A., KORZEKWA, K. R., GROGAN, J., GONZALEZ, F. J. and HARRIS, J. W., 1994, Selective biotransformation of taxol to 6 alpha-hydroxytaxol by human cytochrome P450 2C8. Cancer Research, 54, 5543-5546.
88. RAMAMOORTHY, Y., YU, A. M., SUH, N., HAINING, R. L., TYNDALE, R. F. and SELLERS, E. M., 2002, Reduced (±)-3,4-methylenedioxymethamphetamine ('Ecstasy') metabolism with cytochrome P450 2D6 inhibitors and pharmacogenetic variants in vitro. Biochemical Pharmacology, 63, 2111-2119.
89. RENWICK, A. B., SURRY, D., PRICE, R. J., LAKE, B. G. and EVANS, D. C., 2000, Metabolism of 7-benzyloxy-4-trifluoromethylcoumarin by human hepatic cytochrome P450 isoforms. Xenobiotica, 30, 955-970.
90. RETTIE, A. E., EDDY, A. C., HEIMARK, L. D., GIBALDI, M. and TRAGER, W. F., 1989, Characteristics of warfarin hydroxylation catalyzed by human liver microsomes. Drug Metabolism and Disposition, 17, 265-270.
91. ROCHAT, B., AMEY, M., GILLET, M. and MEYER, U. A., 1997, Identification of three cytochrome P450 isozymes involved in N-demethylation. Pharmacogenetics, 7, 1-10.
92. RODRIGUES, A. D., SURBER, B. W., YAO, Y., WONG, S. L. and ROBERTS, E. M., 1997, [O-ethyl 14C]phenacetin O-deethylase activity in human liver microsomes. Drug Metabolism and Disposition, 25, 1097-1100.
93. ROWLAND-YEO, K., ROSTAMI-HODJEGAN, A. and TUCKER, G. T., 2004, Abundance of cytochromes P450 in human liver: a meta analysis. British Journal of Clinical Pharmacology (in press).
94. SHIMADA, T., GILLAM, E. M., SUTTER, T. R., STRICKLAND, P. T., GUENGERICH, F. P. and YAMAZAKI, H., 1997, Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metabolism and Disposition, 25, 617-622.
95. SHIMADA, T., TSUMURA, F. and YAMAZAKI, H., 1999, Prediction of human liver microsomal oxidations of 7-ethoxycoumarin and chlorzoxazone with kinetic parameters of recombinant cytochrome P-450 enzymes. Drug Metabolism and Disposition, 27, 1274-1280.
96. SHIMADA, T., TSUMURA, F., YAMAZAKI, H., GUENGERICH, F. P. and INOUE, K., 2001, Characterization of (±)-bufuralol hydroxylation activities in liver microsomes of Japanese and Caucasian subjects genotyped for CYP2D6. Pharmacogenetics, 11, 143-156.
97. 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.
98. SHU, Y., WANG, L. S., Xu, Z. H., HE, N., XIAO, W. M., WANG, W., HUANG, S. L. and ZHOU, H. H., 2000, 5-hydroxylation of omeprazole by human liver microsomal fractions from Chinese populations related to CYP2C19 gene dose and individual ethnicity. Journal of Pharmacology and Experimental Therapeutics, 295, 844-851.
99. SKJELBO, E. and BROSEN, K., 1992, Inhibitors of imipramine metabolism by human liver microsomes. British Journal of Clinical Pharmacology, 34, 256-261.
100. SNAWDER, J. E., ROE, A. L., BENSON, R. W., CASCIANO, D. A. and ROBERTS, D. W., 1994, Cytochrome P450-dependent metabolism of acetaminophen in four human transgenic lymphoblastoid cell lines. Pharmacogenetics, 4, 43-46.
101. STORMER, E., VON MOLTKE, L. L. and GREENBLATT, D. J., 2000, Scaling drug biotransformation data from cDNA-expressed cytochrome P-450 to human liver: a comparison of relative activity factors and human liver abundance in studies of mirtazapine metabolism. Journal of Pharmacology and Experimental Therapeutics, 295, 793-801.
102. SULLIVAN-KLOSE, T. H., GHANAYEM, B. I., BELL, D. A., ZHANG, Z. Y., KAMINSKY, L. S., SHENFIELD, G. M., MINERS, J. O., BIRKETT, D. J. and GOLDSTEIN, J. A., 1996, The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics, 6, 341-349.
103. TAGUCHI, M., IMAOKA, S., YOSHII, K., KOBAYASHI, K., HOSOKAWA, M., SHIMADA, N., FUNAE, Y. and CHIBA, K., 2001, Kinetics of testosterone 6beta-hydroxylation in the reconstituted system with similar ratios of purified CYP3A4, NADPH-cytochrome p450 oxidoreductase and cytochrome B5 to human liver microsomes. Research Communications in Molecular Pathology and Pharmacology, 109, 53-63.
104. TAKANASHI, K., TAINAKA, H., KOBAYASHI, K., YASUMORI, T., HOSAKAWA, M. and CHIBA, K., 2000, CYP2C9 Ile359 and Leu359 variants: enzyme kinetic study with seven substrates. Pharmacogenetics, 10, 95-104.
105. TANG, C., SHOU, M. and RODRIGUES, A. D., 2000, Substrate-dependent effect of acetonitrile on human liver microsomal cytochrome P450 2C9 (CYP2C9) activity. Drug Metabolism and Disposition, 28, 567-572.
106. 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, 401-407.
107. 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.
108. 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.
109. THUMMEL, K. E., O'SHEA, D., PAINE, M. F., SHEN, D. D., KUNZE, K. L., PERKINS, J. D. and WILKINSON, G. R., 1996, Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clinical Pharmacology and Therapeutics, 59, 491-502.
110. TRACY, T. S., MARRA, C., WRIGHTON, S. A., GONZALEZ, F. J. and KORZEKWA, K. R., 1997, Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. European Journal of Clinical Pharmacology, 52, 293-298.
111. TRANSON, C., LECOEUR, S., LEEMANN, T., BEAUNE, P. and DAYER, P., 1996, Interindividual variability in catalytic activity and immunoreactivity of three major human liver cytochrome P450 isozymes. European Journal of Clinical Pharmacology, 51, 79-85.
112. TUCKER, G. T., 1992, The rational selection of drug interaction studies: implications of recent advances in drug metabolism. International Journal of Clinical Pharmacology, Therapeutics and Toxicology, 30, 550-553.
113. TUCKER, G. T., HOUSTON, J. B. and HUANG, S. M., 2001, Optimizing drug development: strategies to assess drug metabolism/transporter interaction potential-toward a consensus. Clinical Pharmacology and Therapeutics, 70, 103-114.
114. VENKATAKRISHNAN, K., VON MOLTKE, L. L. and GREENBLATT, D. J., 1998a, Relative quantities of catalytically active CYP 2C9 and 2C19 in human liver microsomes: application of the relative activity factor approach. Journal of Pharmaceutical Science, 87, 845-853.
115. VENKATAKRISHNAN, K., VON MOLTKE, L. L. and GREENBLATT, D. J., 2002, Evaluation of Supermix as an in vitro model of human liver microsomal drug metabolism. Biopharmaceutics and Drug Disposition, 23, 183-190.
116. VENKATAKRISHNAN, K., VON MOLTKE, L. L., COURT, M. H., HARMATZ, J. S., CRESPI, C. L. and GREENBLATT, D. J., 2000a, Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metabolism and Disposition, 28, 1493-1504.
117. VENKATAKRISHNAN, K., VON MOLTKE, L. L., DUAN, S. X., FLEISHAKER, J. C., SHADER, R. I. and GREENBLATT, D. J., 1998b, Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man. Journal of Pharmacy and Pharmacology, 50, 265-274.
118. VENKATAKRISHNAN, K., VON MOLTKE, L. L., OBACH, R. S. and GREENBLATT, D. J., 2000b, Microsomal binding of amitriptyline: effect on estimation of enzyme kinetic parameters in vitro. Journal of Pharmacology and Experimental Therapeutics, 293, 343-350.
119. VON MOLTKE, L. L., GREENBLATT, D. J., GRASSI, J. M., GRANDA, B. W., VENKATAKRISHNAN, K., SCHMIDER, J., HARMATZ, J. S. and SHADER, R. I., 1998, Multiple human cytochromes contribute to biotransformation of dextromethorphan in-vitro: role of CYP2C9, CYP2C19, CYP2D6, and CYP3A. Journal of Pharmacy and Pharmacology, 50, 997-1004.
120. VOORMAN, R. L., PAYNE, N. A., WIENKERS, L. C., HAUER, M. J. and SANDERS, P. E., 2001, Interaction of delavirdine with human liver microsomal cytochrome P450: inhibition of CYP2C9, CYP2C19, and CYP2D6. Drug Metabolism and Disposition, 29, 41-47.
121. WANG, J. S., BACKMAN, J. T., KIVISTO, K. T. and NEUVONEN, P. J., 2000, Effects of metronidazole on midazolam metabolism in vitro and in vivo. European Journal of Clinical Pharmacology, 56, 555-559.
122. WANG, R. W., NEWTON, D. J., SCHERI, T. D. and LU, A. Y., 1997, Human cytochrome P450 3A4-catalyzed testosterone 6 beta-hydroxylation and erythromycin N-demethylation. Competition during catalysis. Drug Metabolism and Disposition, 25, 502-507.
123. WILSON, Z. E., ROSTAMI-HODJEGAN, A., BURN, J. L., TOOLEY, A., BOYLE, J., ELLIS, S. W. and TUCKER, G. T., 2003, Inter-individual variability in levels of human microsomal protein and hepatocellularity per gram of liver. British Journal of Clinical Pharmacology, 56, 433-440.
124. WONG, M., 1999, The evaluation of in vitro methods as predictors of in vivo drug interactions. PhD thesis, University of Sheffield.
125. YAMAZAKI, H., INOUE, K., CHIBA, K., OZAWA, N., KAWAI, T., SUZUKI, Y., GOLDSTEIN, J. A., GUENGERICH, F. P. and SHIMADA, T., 1998, Comparative studies on the catalytic roles of cytochrome P450 2C9 and its Cys-and Leu-variants in the oxidation of warfarin, flurbiprofen, and diclofenac by human liver microsomes. Biochemical Pharmacology, 56, 243-251.
126. YAMAZAKI, H., INOUE, K., SHAW, P. M., CHECOVICH, W. J., GUENGERICH, F. P. and SHIMADA, T., 1997, Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: effects of contents of these two forms in individual human samples. Journal of Pharmacology and Experimental Therapeutics, 283, 434-442.
127. m diazepam N-demethylase in livers of poor metabolizers for 5-mephenytoin 4′-hydroxylation. Pharmacogenetics, 4, 323-331.
128. YU, A. and HAINING, R. L., 2001, Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metabolism and Disposition, 29, 1514-1520.
129. YUN, C. H., MILLER, G. P. and GUENGERICH, F. P., 2000, Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants. Biochemistry, 39, 11319-11329.
130. ZANGER, U. M., FISCHER, J., RAIMUNDO, S., STUVEN, T., EVERT, B. O., SCHWAB, M. and EICHELBAUM, M., 2001, Comprehensive analysis of the genetic factors determining expression and function of hepatic CYP2D6. Pharmacogenetics, 11, 573-585.
131. ZHANG, Z., FASCO, M. J., HUANG, Z., GUENGERICH, F. P. and KAMINSKY, L. S., 1995, Human cytochromes P4501A1 and P4501A2: R-warfarin metabolism as a probe. Drug Metabolism and Disposition, 23, 1339-1346.
132. ZUEGGE, J., SCHNEIDER, G., COASSOLO, P. and LAVE, T., 2001, Prediction of hepatic metabolic clearance: comparison and assessment of prediction models. Clinical Pharmacokinetics, 40, 553-563.