Fully automated analysis of activities catalysed by the major human liver cytochrome P450 (CYP) enzymes: Assessment of human CYP inhibition potential

Xenobiotica

Volumn 29, Issue 1, 1999, Pages 53-75

  Moody, G C ^a   Griffin, S J ^a   Mather, A N ^b   McGinnity, D F ^a   Riley, R J ^a  

^a Dept of Phys/Metabolic Sciences ^*  (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; COMPLEMENTARY DNA; CYTOCHROME P450; DEXTROMETHORPHAN; DIAZEPAM; ERYTHROMYCIN; ETHOXYRESORUFIN; FURAFYLLINE; KETOCONAZOLE; NAPROXEN; OMEPRAZOLE; QUINIDINE; SULFAPHENAZOLE;

ANIMAL CELL; ARTICLE; AUTOANALYSIS; CONTROLLED STUDY; DEMETHYLATION; DRUG SCREENING; ENZYME INHIBITION; ENZYME SPECIFICITY; EXTRACTION; FLUOROMETRY; HUMAN; HUMAN CELL; LIVER MICROSOME; NONHUMAN; RADIOMETRY;

AUTOMATION; CARBON RADIOISOTOPES; CHEMISTRY, CLINICAL; CYTOCHROME P-450 ENZYME SYSTEM; DRUG DESIGN; ENZYME INHIBITORS; FLUORESCENT DYES; FORMIC ACIDS; HUMANS; INHIBITORY CONCENTRATION 50; METHYLATION; MICROSOMES, LIVER; RADIOMETRY; REPRODUCIBILITY OF RESULTS; SUBSTRATE SPECIFICITY; TECHNOLOGY, PHARMACEUTICAL;

EID: 0032970480     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982599238812     Document Type: Article

References (79)

1. AHMAD, S. R. and WOLFE, S. M., 1995, Cisapride and torsades de pointes. Lancet, 345, 508.
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. ANDERSSON, T., MINERS, J. O., VERONESE, M. E., TASSANEEYAKUL, W., 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.
4. AOYAMA, T., KORZEKWA, K., NAGATA, K., GILLETTE, J., GELBOIN, H. V. and GONZALEZ, F. J., 1990, Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s. Endocrinology, 126, 3101-3106.
5. AYRTON, J., PLUMB, R., LEAVENS, W. J., MALLETT, D., DICKINS, M. and DEAR, G. J., 1998, Application of a generic fast gradient liquid chromatography tandem mass spectrometry method for the analysis of cytochrome P450 probe substrates. Rapid Communications in Mass Spectroscomy, 12, 217-224.
6. 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.
7. 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.
8. BERTZ, R. J. and GRANNEMAN, G. R., 1997, Use of in vitro and in vivo data to estimate the likelihood of metabolic pharmacokinetic interactions. Clinical Pharmacokinetics, 32, 210-258.
9. 14C-methyl]caffeine. Xenobiotica, 25, 917-927.
10. BLOOMER, J. C., WOODS, F. R., HADDOCK, R. E., LENNARD, M. S. and TUCKER, G. T., 1992, The role of cytochrome P4502D6 in the metabolism of paroxetine by human liver microsomes. British Journal of Clinical Pharmacology, 33, 521-523.
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. BOURRIE, M., MEUNIER, V., BERGER, Y. and FABRE, G., 1996, Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalysed by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 277, 321-332.
13. BROLY, F., LIBERSA, C., LHERMITT, M. and DUPUIS, B., 1990, Inhibitory studies of mexiletine and dextromethorphan oxidation in human liver microsomes. Biochemical Pharmacology, 39, 1045-1053.
14. BRØSEN, K., 1995, Drug interaction and the cytochrome P450 system. Clinical Pharmacokinetics, 29 (suppl. 1), 20-25.
15. CHANG, T. K. H., GONZALEZ, F. J. and WAXMAN, D. J., 1994, Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Archives of Biochemistry and Biophysics, 311, 437-422.
16. 50) of an enzymatic reaction. Biochemical Pharmacology, 22, 3099-3108.
17. CHING, M. S., BLAKE C. L., GHABRIAL, H., WYNNE ELLIS, S., LENNARD, M. S., TUCKER, G. T. and SMALLWOOD, R. A., 1995, Potent inhibition of yeast-expressed CYP2D6 by dihydroquinidine, quinidine, and its metabolites. Biochemical Pharmacology, 50, 833-837.
18. CLARKE, S. E., AYRTON, J. C. and CHENERY, R. J., 1994, Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica, 24, 517-526.
19. COOK, C. S., HAUSWALD, C., OPPERMANN, J. A. and SCHOENHARD, G. L., 1993, Involvement of cytochrome P4503A in the metabolism of potassium canrenoate to an epoxide: mechanism of inhibition of the epoxide formation by spiranalactone and its sulfur-containing metabolite. Journal of Pharmacology and Experimental Therapeutics, 266, 1-7.
20. CRESPI, C. L., MILLER, V. P. and PENMAN, B. W., 1997, Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450. Annals of Biochemistry, 248, 188-190.
21. CRESPI, C. L. and PENMAN, B. W., 1997, Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug-interactions. Advances in Pharmacology, 43, 171-188.
22. 1 activity. Clinical Pharmacology and Therapeutics, 45, 34-40.
23. 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.
24. DUCHARME, J., ABDULLAH, S. and WAINER, I. W., 1996, Dextromethorphan as an in vivo probe for the simultaneous determination of CYP2D6 and CYP3A activity. Journal of Chromatography B, 678, 113-128.
25. FISCHER, V., VOGELS, B., MAURER, G. and TYNES, R. E., 1992, The antipsychotic clozapine is metabolised by the polymorphic human microsomal and recombinant cytochrome P450 2D6. Journal of Pharmacology and Experimental Therapeutics, 260, 1355-1360.
26. FLOCKHART, D. A., 1995, Drug interactions and the cytochrome P450 system. Clinical Pharmacokinetics, 29(suppl. 1), 45-52.
27. FONNE-PFISTER, R. and MEYER, U. A., 1988, Xenobiotic and endobiotic inhibitors of cytochrome P450 db1 function, the target of the debrisoquine/sparteine type polymorphism. Biochemical Pharmacology, 37, 3829-3835.
28. 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.
29. GORSKI, J. C., JONES, D. R., WRIGHTON, S. A. and HALL, S. D., 1994, Characterisation of dextromethorphan N-demethylation by human liver microsomes: contribution of the cytochrome P450 3A subfamily. Biochemical Pharmacology, 48, 173-182.
30. GUENGERICH, F. P., GILLAM, E. M. J., OHMORI, S., SANDHU, P., BRIAN, W. R., SARI, M. and IWASAKI, M., 1993, Expression of human cytochrome P450 enzymes in yeast and bacteria and relevance to studies on catalytic specificity. Toxicology, 82, 21-37.
31. HA, H. R., CHEN, J., FREIBURGHAUS, A. U. and FOLLATH, F., 1995, Metabolism of theophylline by cDNA-expressed human cytochromes P450. British Journal of Clinical Pharmacology, 39, 321-326.
32. 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.
33. HONIG, P. K., WORTHAM, D. C., ZAMANI, K., CONNER, D. P., MULLIN, J. C. and CANTILENA, L. R., 1993, Terfenadine-ketoconazole interaction: pharmacokinetic and electrocardiographic consequences. Journal of the American Medical Association, 269, 1513-1518.
34. JONES, D. R., GORSKI, C., HAEHNER, B. D., O'MARA, E. M. and HALL, S. D., 1996, Determination of cytochrome P450 3A4/5 activity in vivo with dextromethorphan N-demethylation. Clinical Pharmacology and Therapeutics, 60, 374-384.
35. JACQZ-AIGRAIN, E., FUNCK-BRENTANO, C. and CRESTEIL, T., 1993, CYP2D6 and CYP3A-dependent metabolism of dextromethorphan in humans. Pharmacogenetics, 3, 197-204.
36. m diazepam N-demethylases. Drug Metabolism and Disposition, 25, 133-139.
37. 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.
38. KERRY, N. L., SOMOGYI, A. A., MIKUS, G. and BOCHNER, F., 1993, Primary and secondary oxidative metabolism of dextromethorphan: in vitro studies with female Sprague-Dawley and dark agouti rat liver microsomes. Biochemical Pharmacology, 45, 833-839.
39. KO, J.-W., SUKHOVA, N., THACKER, D., CHEN, P. and FLOCKHART, D. A., 1997, Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metabolism and Disposition, 25, 853-862.
40. KRONBACH, T., MATHYS, D., GUT, J., CATIN, T. and MEYER, U. A., 1987, High-performance liquid chromotographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase and dextromethorphan O-demethylase in microsomes and purified cytochrome P450 isozymes of human liver. Annals of Biochemistry, 162, 24-32.
41. KÜPFER, A., SCHMID, B., PREISIG, R. and PFAFF, G., 1984, Dextromethorphan as a safe probe for debrisoquine hydroxylation polymorphism. Lancet, ii, 517-518.
42. MANCY, A., BROTO, P., DIJOLS, S., DANSETTE, P. M. and MANSUY, D., 1995, The substrate binding site of human liver cytochrome P4502C9: an approach using designed tienilic acid derivatives and molecular modelling. Biochemistry, 34, 10365-10375.
43. MANCY, A., DIJOLS, S., POLI, S., GUENGERICH, F. P. and MANSUY, D., 1996, Interaction of sulfaphenazole derivatives with human liver cytochromes P450 2C: molecular origin of the specific inhibitory effects of sulfaphenazole on CYP2C9 and consequences for the substrate binding site topology of CYP2C9. Biochemistry, 35, 16205-16212.
44. MINERS, J. O., COULTER, S., TUKEY, R. H., VERONESE, M. E. and BIRKETT, D. J., 1996, Cytochromes P450, 1A2 and 2C9 are responsible for the human hepatic O-demethylation of R-and S-naproxen. Biochemical Pharmacology, 51, 1003-1008.
45. 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.
46. OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370-2378.
47. ONO, S., HATANAKA, T., HOTTA, H., SATOH, T., GONZALEZ, F. J. and TSUTSUI, M., 1996a, 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.
48. ONO, S., HATANAKA, T., MIYAZAWA, S., TSUTSUI, M., AOYAMA, T., GONZALEZ, F. J. and SATOH, T., 1996b, Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: role of CYP2B6, 2C19 and the 3A subfamily. Xenobiotica, 26, 1155-1166.
49. PASTRAKULJIC, A., TANG, B. K., ROBERTS, E. A. and KALOW, W., 1997, Distinction of CYP1A1 and CYP1A2 activity by selective inhibition using fluvoxamine and isosafrole. Biochemical Pharmacology, 53, 531-538.
50. PECK, C. C., TEMPLE, R. and COLLINS, J. M., 1993, Understanding consequences of concurrent therapies. Journal of the American Medical Association, 269, 1550-1552.
51. PICHARD, L., FABRE, I., FABRE, G., DOMERGUE, J., AUBERT, B. S., MOUARD, G. and MAUREL, P., 1990, Cyclosporin A drug interactions: screening for inducers and inhibitors of cytochrome P450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metabolism and Disposition, 18, 595-606.
52. PRITCHARD, P. M., GLANCEY, M. J., BLAKE, J. A. R., 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.
53. 14C]erythromycin. Journal of Pharmacology and Toxicological Methods, 38, 189-193.
54. RILEY, R. J., LAMBERT, C., COOPER, A. E., RICHMOND, H., HALL, M., JORDAN, M. C., LOGAN, C. J. and CLARK, B., 1995, Induction of rodent hepatic drug-metabolizing enzyme activities by the novel anticonvulsant remacemide hydrochloride. Drug Metabolism and Disposition, 23, 922-928.
55. RODRIGUES, A. D., 1997, Preclinical drug metabolism in the age of high throughput screening: an industrial perspective. Pharmaceutical Research, 14, 1504-1510.
56. 14C] naproxen O-demethylase activity in human liver microsomes: evidence for the involvement of cytochrome P4501A2 and P4502C9/10. Drug Metabolism and Disposition, 24, 126-136.
57. 14C] dextromethorphan. Annals of Biochemistry, 219, 309-320.
58. 14C] phenacetin O-deethylase activity in human liver microsomes. Drug Metabolism and Disposition, 25, 1097-1100.
59. pol-6, p. 47.
60. SCHMIDER, J., GREENBLATT, D. J., FOGELMAN, S. M., VON MOLTKE, L. L. and SHADER, R. I., 1997, Metabolism of dextromethorphan in vitro: involvement of cytochromes P450 2D6 and 3A3/4, with a possible role of 2E1. Biopharmacology and Drug Disposition, 18, 227-240.
61. 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 P4501A2 in man. British Journal of Clinical Pharmacology, 29, 651-663.
62. SHIMADA, T., YAMAZAKI, H., MIMURA, M., YUKIHARU, I. and GUENGERICH, F. P., 1994, Interindividual variations in human liver cytochrome P450 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.
63. TASSANEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., MCMANUS, M. E., TUKEY, R. H. and MINERS, J. O., 1994, Direct characterisation of the selectivity of furafylline as an inhibitor of cytochromes P450 1A1 and 1A2. Pharmacogenetics, 4, 281-284.
64. TASSANEEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., MCMANUS, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELBOIN, H. V. and MINERS, J. O., 1993, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401-407.
65. 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.
66. TRACY, T. S., MARRA, C., WRIGHTON, S. A., GONZALEZ, F. J. and KORZEKWA, K. R., 1997, Involvement of multiple cytochrome P450s in naproxen O-demethylation. European Journal of Clinical Pharmacology, 52, 293-298.
67. UENG, Y.-F., KUWBARA, T., CHUN, Y.-J. and GUENGERICH, F. P., 1997, Cooperativity in oxidations catalysed by cytochrome P450 3A4. Biochemistry, 36, 310-381.
68. VAN MOLTKE, L. L., GREENBLATT, J. G., GRASSI, J. G., GRANDA, B. W., SCHMIDER, J., HARMATZ, J. S. and SHADER, R. I., 1998, Reevaluation of the specificity of dextromethorphan as an index substrate. Clinical Pharmacology and Therapeutics, 63, 227.
69. WATANABE, N., KAMEI, S., OHKUBO, A., YAMANAKA, M., OHSAWA, S., MAKINO, K. and TOKUDA, K., 1986, Urinary protein as measured with a pyrogallol red-molybdate complex, manually and in a Hitachi 726 automated analyzer. Clinical Chemistry, 32, 1551-1554.
70. WIENKERS, L. C., WURDEN, C. J., STORCH, E., KUNZE, K. L., RETTIE, A. E. and TRAGER, W. F., 1996, Formation of (R)-8-hydroxywarfarin in human liver microsomes: a new metabolic marker for the (S)-mephenytoin hydroxylase, P4502C19. Drug Metabolism and Disposition, 24, 610-615.
71. WU, D., OTTON, S. V., MORROW, P., INABA, T., KALOW, W. and SELLERS, E. M., 1993, Human hepatic cytochrome P450 2D6-like activity in nonhuman primates: catalytic characterization in vitro. Journal of Pharmacology and Experimental Therapeutics, 266, 715-719.
72. YAMAZAKI, H., INOUE, K., SHAW, P. M., CHECOVICH, W. J., GUENGERICH, 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.
73. YANG, C. S., PATTEN, C. J., ISHIZAKI, H. and YOO, J. S. H., 1991, Induction, purification and characterisation of cytochrome P450IIE. Methods in Enzymology, 206, 595-603.
74. YANG, T. J., SHOU, M., KORZEKWA, K. R., GONZALEZ, F. J., GELBOIN, H. V. and YANG, S. K., 1998, Role of cDNA-expressed human cytochromes P450 in the metabolism of diazepam. Biochemical Pharmacology, 55, 889-896.
75. 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.
76. ZHANG, X.-J. and THOMAS, P. E., 1996, Erythromycin as a specific substrate for cytochrome P4503A isozyme and identification of a high-affinity erythromycin N-demethylase in adult female rats. Drug Metabolism and Disposition, 24, 23-28.
77. ZHAO, X. J. and ISHIZAKI, T., 1997, Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. British Journal of Clinical Pharmacology, 44, 505-511.
78. ZOMORODI, K. and HOUSTON, J. B., 1996, Diazepam-omeprazole inhibition interaction: an in vitro investigation using human liver microsomes. British Journal of Clinical Pharmacology, 42, 157-162.
79. ZOMORODI, K. and HOUSTON, J. B., 1997, Selectivity of omeprazole inhibition towards rat liver cytochromes P450. Xenobiotica, 27, 49-58.