CYP3A4-mediated hepatic metabolism of the HIV-1 protease inhibitor saquinavir in vitro

References

• AUNGST, B. J., 1999, P-glycoprotein, secretory transport, and other barriers to the oral delivery of anti-HIV drugs. Advances in Drug Delivery Review, 39, 105–116.
   PubMed Web of Science ®Google Scholar
• BALDWIN, S. J., BLOOMER, J. C., SMITH, G. J., AYRTON, A. D., CLARKE, S. E. and CHENERY, R. J., 1995, Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica, 25, 261–270.
   PubMed Web of Science ®Google Scholar
• BIRKETT, D. J., MACKENZIE, P. I., VERONESE, M. E. and MINERS, J. O., 1993, In vitro approaches can predict human drug metabolism. TIPS, 4, 292–294.
   Google Scholar
• CHANG, T. K. H., GONZALEZ, F. J. and WAXMAN, D. J., 1994, Evaluation of triacetyloleandomycin, ct-naphthofiavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochrome P450. Archives of Biochemical Biophysics, 311, 437–442.
   Google Scholar
• CHIBA, M., HENSLEIGH, M. and LIN, J. L., 1997, Hepatic and intestinal metabolism of indinavir, an HIV protease inhibitor, in rat and human microsomes. Major role of CYP3A. Biochemical Pharmacology, 53, 1187–1195.
   PubMed Web of Science ®Google Scholar
• CRAIG, J. C., DUNCAN, I. B., HOCKLEY, D., GRIEF, C., ROBERTS, N. A. and MILLS, J. S., 1991, Antiviral properties of Ro 31-8959, an inhibitor of human immunodeficiency virus (HIV) proteinase. Antiviral Research, 16, 295–305.
   PubMed Web of Science ®Google Scholar
• DECKER, C. J., LAITINER, L. M., BRIDSON, G. W., RAYBUCK, S. A., TUNG, R. D. and CHATURREDI, P. R., 1998, Metabolism of amprenavir in liver microsomes: role of CYP3A4 inhibition for drug interactions. Journal of Pharmaceutical Science, 87, 803–807.
   PubMed Web of Science ®Google Scholar
• EAGLING, V. A., BACK, D. J. and BARRY, M. G., 1997, Differential inhibition of cytochrome P450 isoforms by the protease inhibitors, ritonavir, saquinavir and indinavir. British Journal of Clinical Pharmacology, 44, 190–194.
   PubMed Web of Science ®Google Scholar
• EAGLING, V. A., THA, J. T. 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.
   PubMed Web of Science ®Google Scholar
• FRRZSIMMONS, M. E. and COLLINS, J. M., 1997, Selective biotransformation of the human immunodeficiency virus protease inhibitor saquinavir by human small intestinal cytochrome P450. Drug Metabolism and Disposition, 25, 256–267.
   PubMedGoogle Scholar
• GENTILE, D. M., TOMLINSON, E. S., MAGGS, J. L., PARK, B. K. and BACK, D. J., 1996, Dexamethasone metabolism by human liver in vitro. Metabolite identification and inhibition of 6-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 277, 105–112.
   PubMed Web of Science ®Google Scholar
• GUENGERICH, F. P., Kim, D. H. and IwAsmo, M., 1991, Role of human cytochrome P450 11E1 in the oxidation of many low molecular weight cancer suspects. Chemical Research in Toxicology, 4, 168–179.
   PubMed Web of Science ®Google Scholar
• HALBERT, J. R., GUENGERICH, F. P., BEND, J. R. and CORREIA, M. A., 1994, Selective inhibitors of cytochromes P450. Toxicology and Applied Pharmacology, 125, 163–175.
   PubMedGoogle Scholar
• HOUSTON, J. B., 1994, Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochemical Pharmacology, 47, 1469–1479.
   PubMed Web of Science ®Google Scholar
• KIM, R. B., FROMM, M. F., WANDEL, C., LEAKE, B., WOOD, A. J. J., RODEN, D. M. and WILKINSON, G. R., 1998, The drug transporter P-glycoprotein limits oral absorption and brain entry of HIV-1 protease inhibitors. Journal of Clinical Investigation, 101, 289–294.
   Google Scholar
• KOLARS, J. C., SCHMIEDLIN-REN, P., SCHUETZ, J. D., FANG, C. and WATKINS, P. B., 1992, Identification of rifampicin-inducible P4503A4 in human small bowel enterocytes. Journal of Clinical Investigation, 90, 1871–1878.
   Google Scholar
• KUMAR, G. N., RODRIGUES, A. D., BUKO, A. M. and DENISSEN, J. F., 1996, Cytochrome P450 mediated metabolism of the HIV-1 protease inhibitor Ritonavir (ABT-538) in human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 277, 23–31.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• LEE, C. G. L., GOTTESMAN, M. M., CARDARELLI, C. O., RAMACHANDRA, M., JEANG, K.-T., AMBUDCAR, S. V., PASTAN, I. and DEY, S., 1998, HIV-1 protease inhibitors are substrates for the MDR1 multidrug transporter. Biochemistry, 37, 3594–3601.
   Google Scholar
• LEWIS, D. V. F., EDDERSHAW, P. J., GLODFARB, P. S. and TARBIT, M. H., 1996, Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica, 26, 1067–1086.
   Google Scholar
• LOWN, K. S., GHOSH, M. and WATKINS, P. B., 1998, Sequences of intestinal and hepatic cytochrome P450 3A4 cDNAs are identical. Drug Metabolism and Disposition, 26, 185–187.
   PubMed Web of Science ®Google Scholar
• LOWN, K. S., MAYO, R. R., LEICHTMAN, A. B., HSIAO, H., TURGEON, K., SCHMEIDLIN-REN, P., BROWN, M. B., Guo, W., Rossi, S. J. BENET, L. Z. and WATKINS, P. B., 1997, Role of intestinal P-glycoprotein (mdrl) in interpatient variation in the oral bioavailability of cyclosporine. Clinical and Pharmacology and Therapeutics, 62, 248–260.
   Google Scholar
• LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein determination with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   PubMed Web of Science ®Google Scholar
• MERRY, C., BARRY, M. G., MULCAHY, F., HALIFAX, K. L. and BACK, D. J., 1997b, Saquinavir pharmacokinetics alone and in combination with nelfinavir in HIV-infected patients. AIDS, 11, F117—F120.
   PubMed Web of Science ®Google Scholar
• MERRY, C., BARRY, M. G., MULCAHY, F., RYAN, M., HEAVEY, J., TPA, J. F., GIBBONS, S. E., BRECKENRIDGE, A. M. and BACK, D. J., 1997a, Saquinavir pharmacokinetics alone and in combination with ritonavir in HIV infected patients. AIDS, 11, F29—F33.
   PubMed Web of Science ®Google Scholar
• NOBLE, S. and FAULDS, D., 1996, Saquinavir. A review of its pharmacology and clinical potential in the management of HIV infection. Drugs, 52, 93–112.
   PubMed Web of Science ®Google Scholar
• PERRY, C. M. and NOBLE, S., 1998, Saquinavir soft-gel capsule formulation. A review of its use in patients with HIV infection. Drugs, 55, 461–486.
   PubMed Web of Science ®Google Scholar
• PROFIT, L., EAGLING, V. A. and BACK, D. J., 1999, Modulation of P-glycoprotein function in human lymphocytes and Caco-2 cell monolayers by HIV-1 protease inhibitors. AIDS, 13, 1623–1627.
   Google Scholar
• PRUEESARITANONT, T., GORHAM, L. M., HOCHMAN, J. H., TIN, L. O. and VYAS, K. P., 1996, Comparative studies of drug metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2-cells. Drug Metabolism and Disposition, 24, 634–642.
   PubMedGoogle Scholar
• SESARDIC, D., Booms, A. R., MURRAY, B. P., 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.
   PubMed Web of Science ®Google Scholar
• STEIMER, J. L., FOTTELER, B., GIESCHKE, R., WILTSHIRE, H. and Buss, N., 1998, Predicting the optimal dose of saquinavir via modelling of dose—exposure and exposure—effect relationships. In M. Danhof and J. L. Steimer (eds), Measurement and Kinetics of In Vivo Drug Effects: Advances in Simultaneous PharmacokineticlPharmacodynamk Modelling (Leiden: Amsterdam Center for Drug Research), pp. 79–86.
   Google Scholar
• VON MOLTKE, L. L., GREENBLATT, D. J., GRASSI, J. M., GRANDA, B. W., DUAN, S. X., FOGELMAN, S. M., DAILY, J. P., HARMATZ, J. S. and SHADER, R. I., 1998, Protease inhibitors as inhibitors of human cyto chromes P450: high risk associated with ritonavir. Journal of Clinical Pharmacology, 38, 106–111.
   PubMed Web of Science ®Google Scholar
• WAXMAN, D. J., ÄTTISANO, C., GUENGERICH, F. P. and LAPENSON, D. P., 1988, Human liver microsomal steroid metabolism. Identification of the major microsomal steroid 60 hydroxylase cytochrome P450 enzyme. Archives in Biochemistry and Biophysics, 290, 160–166.
   Google Scholar
• WAXMAN, D. J., LAPENSON, D. P., ÄOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J. and KORZEKWA, K., 1991, Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Archives in Biochemistry and Biophysics, 290, 160–166.
   Google Scholar
• WILTSHIRE, H. R., PRIOR, K. J., DHESI, J., TRACH, F., SCHLAGETER, M. and SCHöNENBERGER, H., 1998, The synthesis of labelled forms of saquinavir. Journal of Labelled Compounds and Radiopharmacology, 41, 1103–1126.
   Google Scholar