In Vitro Inhibitory Effect of 1-Aminobenzotriazole on Drug Oxidations Catalyzed by Human Cytochrome P450 Enzymes: A Comparison with SKF-525A and Ketoconazole

Drug Metabolism and Pharmacokinetics

Volumn 18, Issue 5, 2003, Pages 287-295

  Emoto, Chie ^a   Murase, Shigeo ^a   Sawada, Yasufusa ^a   Iwasaki, Kazuhide ^a   Jones, Barry C ^a   Yuasa, Hiroaki ^b  

^a PFIZER INC   (United States)

^b NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

1 aminobenzotriazole (ABT); Cytochrome P450 (CYP); human; SKF 525A; ketoconazole

Indexed keywords

EID: 28144461609     PISSN: 13474367     EISSN: 18800920     Source Type: Journal    
DOI: 10.2133/dmpk.18.287     Document Type: Article

References (29)

1. Guengrich, F. P.: Reactions and significance of cytochrome P-450 enzymes. J. Biol. Chem., 266: 10019-10022 (1991).
2. Krishna, D. R. and Klotz, U.: Extrahepatic metabolism of drugs in humans. Clin. Pharmacokinet., 26: 144-160 (1994).
3. Spatzenegger, M. and Jaeger, W.: Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metab. Rev., 27: 397-417 (1995).
4. Ortiz de Montellano, P. R., and Mathews, J. M.: Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Biochem. J., 195: 761-764 (1981).
5. Mugford, C. A., Mortillo, M., Mico, B. A. and Tarloff, J. B.: 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats. Fundam. Appl. Toxicol., 19: 43-49 (1992).
6. Mathews, J. M., Dostal, L. A. and Bend, J. R.: Inactivation of rabbit pulmonary cytochrome P-450 in microsomes and isolated perfused lungs by the suicide substrate 1-aminobenzotriazole. J. Pharmacol. Exp. Ther., 235: 186-190 (1985).
7. Woodcroft, K. J. and Bend, J. R.: N-Aralkylated derivatives of 1-aminobenzotriazole as isozyme-selective, mechanism-based inhibitors of guinea pig hepatic cytochrome P-450 dependent monooxygenase activity. Can. J. Physiol. Pharmacol., 68: 1278-1285 (1990).
8. Guengerich, F. P.: Cytochrome P-450 3A4: Regulation and role in drug metabolism. Annu. Rev. Pharmacol. Toxicol., 39: 1-17 (1999).
9. Wang, R. W., Newton, D. J., Liu, N., Atkins, W. M. and Lu. A. Y.: Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent. Drug Metab. Dispos., 28: 360-366 (2000).
10. Kenworthy, K. E., Bloomer, J. C., Clarke, S. E. and Houston, J. B.: CYP3A4 drug interactions: correlation of 10 in vitro probe substrates. Br. J. Clin. Pharmacol., 48: 716-727 (1999).
11. Ortiz de Montellano, P. R., Mathews, J. M. and Langry, K. C.: Autocatalytic inactivation of cytochrome P-450 and chloroperoxidase by 1-aminobenzotriazole and other aryne precursors. Tetrahedron, 40: 511-519 (1984).
12. Chung, W. G.' Park, C. S., Roh, H. K., Lee, W. K. and Cha Y. N.: Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn. J. Pharmacol., 84: 213-220 (2000).
13. Venkatakrishnan, K., von Moltke, L. L. and Greenblatt, D. J.: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin. Pharmacokinet., 38: 111-180 (2000).
14. Huang, Z. and Waxman, D. J.: Modulation of cy-clophosphamide-based cytochrome P450 gene therapy using liver P450 inhibitors. Cancer Gene Ther., 8: 450-458 (2001).
15. Schenkman, J. B., Wilson, B. J. and Cinti, D. L.: Diethylaminoethyl 2,2-diphenylvalerate HCl (SKF-525A)-In vivo and in vitro effects of metabolism by rat liver microsomes-formation of an oxygenated complex. Biochem. Pharmacol., 21: 2373-2383 (1972).
16. Leblond, F. A., Giroux, L., Villeneuve, J. P. and Pichette, V.: Decreased in vivo metabolism of drugs in chronic renal failure. Drug Metab. Dispos., 28: 1317-1320 (2000).
17. Niwa, T., Tsutsui, M., Kishimoto, K., Yabusaki, Y., Ishibashi, F. and Katagiri, M.: Inhibition of drug-metabolizing enzyme activity in human hepatic cytochrome P450s by bisphenol A. Biol Pharm Bull, 23: 498-501 (2000).
18. Maurice, M., Pichard, L., Daujat, M., Fabre, I., Joyeux, H.' Domergue, J. and Maurel, P.: Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture. FASEB J., 6: 752-758 (1992).
19. Back, D. J., Tjia, J. F., Karbwang, J. and Colbert, J.: In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sul-phonamides and quinolines. Br. J. Clin. Pharmacol., 26: 23-29 (1988).
20. Hall, S. D.' Guengerich, F. P., Branch, R. A. and Wilkinson, G. R.: Characterization and inhibition of mephenytoin 4-hydroxylase activity in human liver microsomes. J. Pharmacol. Exp. Ther., 240: 216-222 (1987).
21. von Moltke, L. L., Greenblatt, D. J., Cotreau-Bibbo, M. M., Duan, S. X., Harmatz, J. S. and Shader, R. I.: Inhibition of desipramine hydroxylation in vitro by serotonin-reuptake-inhibitor antidepressants, and by quinidine and ketoconazole: a model system to predict drug interactions in vivo. J. Pharmacol. Exp. Ther., 268: 1278-1283 (1994).
22. Newton, D. J., Wang, R. W. and Lu, A. Y.: Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Meta. Dispos., 23: 154-158 (1995).
23. Nakajima, M., Tane, K., Nakamura, S., Shimada, N., Yamazaki, H. and Yokoi, T.: 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 b5 in the expression system and the differences in the marker activities. J. Pharm. Sci., 91: 952-963 (2002).
24. Kobayashi, K., Nakajima, M., Oshima, K., Shimada, N.' Yokoi, T. and Chiba, K.: Involvement of CYP2E1 as a low-affinity enzyme in phenacetin O-deethylation in human liver microsomes. Drug Metab. Dispos., 27: 860-865 (1999).
25. Yamazaki, H., Suzuki, M., Tane, K., Shimada, N., Nakajima, M. and Yokoi, T.: In vitro inhibitory effects of troglitazone and its metabolites on drug oxidation activities of human cytochrome P450 enzymes: comparison with pioglitazone and rosiglitazone. Xenobiotica, 30: 61-70 (2000).
26. Obach, R. S. and Reed-Hagen, A. E.: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab. Dispos., 30: 831-837 (2002).
27. Ohyama, K., Nakajima, M., Nakamura, S., Shimada, N.' Yamazaki, H. and Yokoi, T.: A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab. Dispos., 28: 1303-1310 (2000).
28. Shimada, T., Tsumura, F. and Yamazaki, H.: Prediction of human liver microsomal oxidations of 7-ethoxycoumarin and chlorzoxazone with kinetic parameters of recombinant cytochrome P-450 enzymes. Drug Metab. Dispos., 27: 1274-1280 (1999).
29. Williams, J. A., Ring, B. J., Cantrell, V. E., Jones, D. R.' Eckstein, J., Ruterbories, K., Hamman, M. A., Hall, S. D. and Wrighton, S. A.: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab. Dispos., 30: 883-891 (2002).