Cytochrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes

Journal of Pharmacology and Experimental Therapeutics

Volumn 277, Issue 1, 1996, Pages 423-431

  Kumar, Gondi N ^a   Rodrigues, A David ^a   Buko, Alexander M ^a   Denissen, Jon F ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DRUG METABOLITE; ETHINYLESTRADIOL; KETOCONAZOLE; NIFEDIPINE; PROTEINASE; RITONAVIR; TROLEANDOMYCIN;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ARTICLE; DRUG MECHANISM; DRUG POTENCY; DRUG TRANSFORMATION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN TISSUE; IONIZATION; LIVER MICROSOME; MASS SPECTROMETRY; OPPORTUNISTIC INFECTION; PRIORITY JOURNAL; PROTEIN DEGRADATION; VIRUS INFECTION;

ANIMALS; ANTIVIRAL AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; HIV PROTEASE INHIBITORS; HUMANS; MICROSOMES, LIVER; RABBITS; RITONAVIR; THIAZOLES; VALINE;

EID: 0030430035     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. ABRAMS, D., COTTON, D. AND MAYER, K.: AIDS/HIV Treatment Directory. AmFar Publications, New York, 1993.
2. BACK, D. J. AND TIJA, J. F.: Comparative effects of the antimycotic drugs ketoconazole, fluconazole, itraconazole and terbinafine on the metabolism of cyclosporin by human liver microsomes. Br. J. Clin. Pharmacol. 32: 624-626, 1991.
3. BERTILSSON, L., MEESE, C. O., YUE, Q. Y., DAHL, M. L., INGELMAN-SUNDBERG, M., JOHANSSON, I., SAWE, J. AND EICHELBAUM, M.: Quinidine inhibition of debrisoquine S(+)-4- and -7-hydroxylations in Chinese of different CYP2D6 genotypes. Pharmacogenetics 3: 94-100, 1993.
4. BUCHERT, E. AND WOOSLEY, R. L.: Clinical implications of variable antiarrhythmic drug metabolism. Pharmacogenetics 2: 2-11, 1992.
5. CHANG, T. K. H., GONZALEZ, F. J. AND WAXMAN, D. J.: Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochrome P450. Arch. Biochem. Biophys. 311: 437-442, 1994.
6. CORNISH-BOWDEN, A : A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors. Biochem. J. 137: 143-144, 1974.
7. CRAIG, J. C., DUNCAN, I. B., HOOKLEY, D., GRIEF, C., ROBERTS, N. A. AND MILLS, J. S.: Antiviral properties of Ro 31-8959, an inhibitor of human immunodeficiency virus (HIV) proteinase. Antiviral Res. 16: 295-305, 1991.
8. FIRKUSNY, L., HEYO, K., KROEMER, K. AND EICHELBAUM, M.: In vitro characterization of cytochrome P450 catalyzed metabolism of the antiemetic tropisetron. Biochem. Pharmacol. 49: 1777-1784, 1995.
9. GILLUM, J. G., ISRAEL, D. S. AND POLK, R. E.: Pharmacokinetic drug interactions with antimicrobial agents. Clin. Pharmacokinet. 25: 450-482, 1993.
10. GUENGERICH, F. P.: Oxidation of 17α-ethynylestradiol by human liver cytochrome P-450. Mol. Pharmacol. 33: 500-508, 1988.
11. GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P. H., KREMERS, P. WOLFF, T. AND WAXMAN, D. J.: Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 261: 5051-5060, 1986.
12. GUENGERICH, F. P., PETERSON, L. A. AND BOCKER, R. H.: Cytochrome P-450-catalyzed hydroxylation and carboxylic acid ester cleavage of Hantzsch pyridine esters. J. Biol. Chem. 263: 8176-8183, 1988.
13. HALPERT, J. R, GUENGERICH, F. P., BEND, J. R. AND CORREIA, M. A.: Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol. 125: 163-175, 1994.
14. HO, D. D., NEUMANN, A. U., PERELSON, A. S., CHEN, W., LEONARD, «J. M. AND MARKOWITZ, M.: Rapid turnover of plasma virions and CD4 lymphocytes in HIV-1 infection. Nature 373: 123-126, 1995.
15. HONIG, P. K., WOOSLEY, R. L., ZAMANI, K., CONNER, D. P. AND CANTILENA, L. R.: Changes in the pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin. Clin. Pharmacol. Ther. 52: 231-238, 1992.
16. KEMPF, D. J., MARSH, K. C., DENISSEN, J. F., MCDONALD, E., VASAVANONDA, S., FLENTGE, C. A., GREEN, B. E., FINA, L., PARK, C. H., KONG, X.-P., WIEBURG, N. E., SALVIDAR, A., RUIZ, L., KATI, W. M., SHAM, H. L., ROBINS, T., STEWART, K D., HSU, A., PLATTNER, J. J., LEONARD, J. M. AND NORBECK, D. W.: ABT-538 is a potent inhibitor of human immunodeficiency virus protease and has high oral bioavailability in humans. Proc. Natl. Acad. Sci. USA 92: 2484-2488, 1995.
17. LAM, P. Y. S., JADHAV, P. K., EYERMANN, C. J., HODGE, C. N., RU, Y., BACHELER, L. T., MEEK, J. L., OTTO, M. J., RAYNER, M. M., WONG, N., CHANG, C.-H., WEBER, P. C., JACKSON, D. A., SHARPE, T. R. AND ERICKSON-VITANEN, S.: Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science 263: 380-384, 1994.
18. LEEMANN, T., DAYER, P. AND MEYER, U. A.: Single-dose quinidine treatment inhibits metoprolol oxidation in extensive metabolizers. Eur. J. Clin. Pharmacol. 29: 739-741, 1986.
19. MAURICE, M., EMILIANI, S., DALET-BELUCHE, I., DERANCOURT, J. AND LANGE, R : Isolation and characterization of cytochrome P450 of the IIA subfamily from human liver microsomes. Eur. J. Biochem. 200: 511-517, 1991.
20. NEWTON, D. J., WANG, R. W. AND LU, A. Y. H.: Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab. Dispos. 23: 154-158, 1995.
21. PENG, H.-M., RANER, G. M., VAZ, A. D. N. AND COON, M. J.: Oxidative cleavage of esters and amides to carbonyl products by cytochrome P450. Arch. Biochem. Biophys. 318: 333-339, 1995.
22. PURBA, H. S., MAGGS, J. L., ORME, M. L'E., BACK, D. J. AND PARK, B. K., The metabolism of 17α-ethynylestradiol by human liver microsomes: Formation of catechol and chemically reactive metabolites. Br. J. Clin. Pharmacol. 23: 447-453, 1987.
23. RAUCY, J. L. AND LASKER, J. M.: Human P450 enzymes associated with the mephenytoin 4-hydroxylation polymorphism. In Human Drug Metabolism: From Molecular Biology to Man, ed. by E. H. Jeffrey, pp. 23-31, CRC Press, Boca Raton, 1993.
24. RODRIGUES, A. D.: Comparison of levels of aldehyde oxidase with cytochrome P450 activities in human liver in vitro. Biochem. Pharmacol. 48: 197-200, 1994.
25. 14C]dextromethorphan. Anal. Biochem. 219: 309-320, 1994.
26. RODRIGUES, A. D., MULFORD, D. J., LEE, R. D., SURBER, B. W., KUKULKA, M. J., FERRERO, J. L., THOMAS, S. B., SHET, M. S. AND ESTABROOK, R. W.: In vitro metabolism of terfenadine by a purified recombinant fusion protein containing cytochrome P450 3A4 (CYP3A4) and NADPH-P450 reductase. Drug Metab. Dispos. 23: 765-775, 1995.
27. RODRIGUES, A. D. AND PROUGH, R. A.: Induction of cytochromes P450IAI and P450IA2 and measurement of catalytic activities. Methods Enzymol. 206: 423-431, 1991.
28. SEGEL, I. H.: Simple inhibition systems. In Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady State Enzyme Systems. ed. by I. H. Segel, pp. 106-144, John Wiley & Sons, New York, NY, 1975.
29. SHIMADA, T., YAMAZAKI, H., MIMURA, M., INUI, Y. AND GUENGERICH, F. P.: Inter-individual 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. J. Pharmacol. Exp. Ther. 270: 414-423, 1994.
30. SHOU, M., GROGAN, J., MANCEWICZ, J. A., KRAUSZ, K. W., GONZALEZ, F. J., GELBOIN, H. V. AND KORZEKWA, K. R.: Activation of CYPSA4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 binding site. Biochemistry 33: 6450-6455, 1994.
31. SMITH, D. A. AND JONES, B. C.: Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes. Biochem. Pharmacol. 44: 2089-2098, 1992.
32. SRIVATSAVA, P. K., YUN, C.-H., BEAUNE, P. H., GED, C. AND GUENGERICH, F. P.: Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4′-hydroxylase cytochrome P-450 enzymes. Mol. Pharmacol. 40: 69-79, 1991.
33. STROBL, G. AND WOLFF, T.: Molecular basis of drug metabolism interactions: A structural model for inhibitors of debrisoquine hydroxylase. NaunynSchmiedeberg's Arch. Pharmacol. 343: R8, 1991.
34. TASSANEEYAKUL, W., VERONESE, M. E., BIRKETT, D. J., GONZALEZ, F. J. AND MINERS, J. O.: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using eDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46: 1975-1981, 1993.
35. VACCA, J. P., BORSEY, B. D., SCHLEIF, W. A., LEVIN, R. B., MCDANIEL, S. L., DARKE, P. L., ZUGAY, J., QUINTERO, J. C., BLAHY, O. M., ROTH, E., SARDANA, V. V., SCHLABACH, A. J., GRAHAM, P. I., CONDRA, J. H., GOTLIB, L., HOLLOWAY, M K., LIN, J., CHEN, L.-W., VASTAG, K., OSTOVIC, D., ANDERSON, P. S., EMINI, E. A. AND HUFF, J. R.: L-735-524: An orally bioavailable human immunodeficiency virus type I protease inhibitor. Proc. Natl. Acad. Sci. USA 91: 4096-4100, 1994.
36. WEST, M. L. AND FAIRLIE, D. P.: Targeting HW-1 protease: a test of drug-design methodologies. Trends Pharmacol. Sci. 16: 67-75, 1995.
37. WRIGHTON, S. A. AND RING, B. J.: Inhibition of human CYP3A catalyzed 1′-hydroxy midazolam formation by ketoconazole, nifedipine, erythromycin, cimetidine and nizatidine. Pharm. Res. 11: 921-924, 1994.
38. WRIGHTON, S. A. AND STEVENS, J. C.: The human hepatic cytochromes P450 involved in drug metabolism. Crit. Rev. Toxicol. 22: 1-21, 1992
39. WRIGHTON, S. A., STEVENS, J. C., BECKER, G. W. AND VANDENBRANDEN, M.: Isolation and characterization of human liver cytochrome P4502C19: Correlation between 2C19 and S-mephenytoin 4′-hydroxylation. Arch. Biochem Biophys. 306: 240-245, 1993.
40. ZHOU, X.-J., ZHOU-PAN, X.-R., GAUTHIER, T., PLACIDI, M., MAUREL, P. AND RAHMANI, R.: Human liver microsomal cytochrome P450 3A isozymes mediated vindesine biotransformation. Biochem. Pharmacol. 45: 853-861, 1993.