In vitro metabolism of gefitinib in human liver microsomes

Reference

• BARKER, A. J., GIBSON, K. H., GRUNDY, W., GODFREY, A. A., BARLOW, J. J., HEALY, M. P., WOODBURN, J. R., ASHTON, S. E., CURRY, B. J., SCARLETT, L., HENTHORN, L. and RICHARDS, L., 2001, Studies leading to the identification of ZD1839 (Iressa): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorganic and Medicinal Chemistry Letters, 11, 1911–1914.
   PubMed Web of Science ®Google Scholar
• CHEN, H., CHEN, W., GAN, L.-S. and MUTLIB, A. E., 2003, Metabolism of (S)-5,6-difluoro-4-cyclopropylethyny1-4-trifluoromethy1-3,4-dihydro-2(1H)-quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics. Drug Metabolism and Disposition, 31, 122–132.
   Google Scholar
• CIARDIELLO, F. and TORTORA, G., 2002, Anti-epidermal growth factor receptor drugs in cancer therapy. Expert Opinion on Investigational Drugs, 11, 755–768.
   PubMed Web of Science ®Google Scholar
• DENISSEN, J. F., GRABOWSKI, B. A., JOHNSON, M. K., BOYD, S. A., UCHIC, J. T., STEIN, H., CEPA, S. and HILL, P., 1994, The orally active renin inhibitor A-74273. In vivo and in vitro morpholine ring metabolism in rats, dogs, and humans. Drug Metabolism and Disposition, 22, 880–888.
   PubMed Web of Science ®Google Scholar
• DI FIORE, P. P., PIERCE, J. H., KRAUS, M. H., SEGATTO, 0., KING, C. R. and AARONSON, S. A., 1987, erbB-2 is a potent oncogene when overexpressed in NIH/3T3 cells. Science, 237, 178–182.
   Google Scholar
• ENNIS, B. W., LIPPMAN, M. E. and DICKSON, R. B., 1991, The EGF receptor system as a target for antitumor therapy. Cancer Investigation, 9, 553–562.
   PubMed Web of Science ®Google Scholar
• FUKUOKA, M., YANO, S., GIACCONE, G., TAMURA, T., NAKAGAWA, K., DOUILLARD, J. Y., NISHIWAKI, Y., VANSTEENKISTE, J., KUDOH, S., RISCHIN, D., EEK, R., HORAI, T., NODA, K., TAKATA, I., SMIT, E., AVERBUCH, S., MACLEOD, A., FEYEREISLOVA, A., DONG, R. P. and BASELGA, J., 2003, Multi-institutional randomized phase II trial of gefitinib for previously treated patients with advanced non-small-cell lung cancer. Journal of Clinical Oncology, 21, 2237–2246.
   PubMed Web of Science ®Google Scholar
• GIBSON, K. H., GRUNDY, W., GODFREY, A. A., WOODBURN, J. R., ASHTON, S. E., CURRY, B. J., SCARLETT, L., BARKER, A. J. and BROWN, D. S., 1997, Epidermal growth factor receptor tyrosine kinase: structure—activity relationships and antitumour activity of novel quinazolines. Bioorganic and Medicinal Chemistry Letters, 7, 2723–2728.
   Web of Science ®Google Scholar
• HERBST, R. S., MADDOX, A. M., ROTHENBERG, M. L., SMALL, E. J., RUBIN, E. H., BASELGA, J., Rojo, F., HONG, W. K., SWAISLAND, H., AVERBUCH, S. D., OCHS, J. and LoRusso, P. M., 2002, Selective oral epidermal growth factor receptor tyrosine kinase inhibitor ZD1839 is generally well-tolerated and has activity in non-small-cell lung cancer and other solid tumors: results of a phase I trial. Journal of Clinical Oncology, 20, 3815–3825.
   PubMed Web of Science ®Google Scholar
• HusKEY, S.-E. W., DEAN, B. J., Doss, G. A., WANG, Z., HOP, C. E. C. A., ANARI, R., FINKE, P. E., ROBICHAUD, A. J., ZHANG, M., WANG, B., STRAUSS, J. R., CUNNINGHAM, P. K., FEENEY. W. P., FRANKLIN, R. B., BAILLIE, T. A. and CHiu, S.-H. L., 2004, The metabolic disposition of aprepitant, a substance P receptor antagonist, in rats and dogs. Drug Metabolism and Disposition, 32, 246–258.
   Google Scholar
• KRIS, M. G., NATALE, R. B., HERBST, R. S., LYNCH, Jr, T. J., PRAGER, D., BELANI, C. P., SCHILLER, J. H., KELLY, K., SPIRIDONIDIS, H., SANDLER, A., ALBAIN, K. S., CELLA, D., WOLF, M. K., AVERBUCH, S. D., OCHS, J. J. and KAY, A. C., 2003, Efficacy of gefitinib, an inhibitor of the epidermal growth factor receptor tyrosine kinase, in symptomatic patients with non-small cell lung cancer. Journal of the American Medical Association, 290, 2149–2158.
   Google Scholar
• MAYERSOHN, M. and GUENTERT, T. W., 1995, Clinical pharmacokinetics of the monoamine oxidase-A inhibitor moclobemide. Clinical Pharnzacokinetics, 29, 292–332.
   PubMed Web of Science ®Google Scholar
• MCKILLOP, D., HUTCHISON, M., PARTRIDGE, E. A., BUSHBY, N., COOPER, C. M. F., CLARKSON-JONES, J. A., HERRON, W. and SWAISLAND, H. C., 2004a, Metabolic disposition of gefitinib, an epidermal growth factor receptor tyrosine kinase inhibitor, in rat, dog and man. Xenobiotica, 34, 917–934.
   Google Scholar
• MCKILLOP, D., PARTRIDGE, E. A., HUTCHISON, M., PARRY, A. C., BARDSLEY, J., WOODMAN, H. M. and SWAISLAND, H. C., 2004b, Pharmacokinetics of gefitinib, an epidermal growth factor receptor tyrosine kinase inhibitor, in rat and dog. Xenobiotica, 34, 901–915.
   PubMed Web of Science ®Google Scholar
• MCKILLOP, D., WILD, M. J., BUTTERS, C. J. and Simuoux, C., 1998, Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica, 28, 845–853.
   PubMed Web of Science ®Google Scholar
• MUTCH, P. J., DEAR, G. J. and IsmAIL, I. M., 2001, Formation of a defiuorinated metabolite of a quinoxaline antiviral drug catalysed by human cytochrome P450 1A2. Journal of Pharmacy and Pharmacology, 53, 403–408.
   PubMed Web of Science ®Google Scholar
• PARK, Y. H., HUDSON, J. E., BARKER, R. C., YORK, B. M. and BRAZZELL, R. K., 1991, Metabolism of the aldose reductase inhibitor AL01567 in man. British Journal of Clinical Pharmacology, 32, 221–227.
   PubMed Web of Science ®Google Scholar
• RANSON, M., HAMMOND, L. A., FERRY, D., KRIS, M., TULLO, A., MURRAY, P. I., MILLER, V., AVERBUCH, S., OCHS, J., MORRIS, C., FEYEREISLOVA, A., SWAISLAND, H. and ROWINSKY, E. K., 2002, ZD1839, a selective oral epidermal growth factor receptor-tyrosine kinase inhibitor, is well tolerated and active in patients with solid, malignant tumors: results of a phase I trial. Journal of Clinical Oncology, 20, 2240–2250.
   PubMed Web of Science ®Google Scholar
• SAINSBURY, J. R., MALCOLM, A. J., APPLETON, D. R., FARNDON, J. R. and HARRIS, A. L., 1985, Presence of epidermal growth factor receptor as an indicator of poor prognosis in patients with breast cancer. Journal of Clinical Pathology, 38, 1225–1228.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., TUGNAIT, M., WILSON, I. D. and NICHOLSON, J. K., 1999, Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in rat: formation of 4-acetamidophenol (paracetamol) and its metabolites via defiuorination and N-acetylation. Xenobiotica, 29, 205–216.
   PubMed Web of Science ®Google Scholar
• SIROTNAK, F. M., ZAKOWSKI, M. F., MILLER, V. A., SCHER, H. I. and KRIS, M. G., 2000, Efficacy of cytotoxic agents against human tumor xenografts is markedly enhanced by coadminis-tration of ZD1839 (Iressa), an inhibitor of EGFR tyrosine kinase. Clinical Cancer Research, 6, 4885–4892.
   PubMed Web of Science ®Google Scholar
• SLAMON, D. J., CLARK, G. M., WONG, S. G., LEVIN, W. J., ULLRICH, A. and MuGuIRE, W. L., 1987, Human breast cancer: correlation of relapse and survival with amplification of the HER-2/neu oncogene. Science, 235, 177–182.
   PubMed Web of Science ®Google Scholar
• SLATTER, J. G., STALKER, D. J., FEENSTRA, K. L., WELSHMAN, I. R., BRUSS, J. B., SAMS, J. P., JOHNSON, M. G., SANDERS, P. E., HAUER, M. J., FAGERNESS, P. E., STRYD, R. P., PENG, G. W. and SHOBE, E. M., 2001, Pharmacokinetics, metabolism and excretion of linezolid following an oral dose of [14C] linezolid to healthy human subjects. Drug Metabolism and Disposition, 29, 1136–1145.
   PubMed Web of Science ®Google Scholar
• SWAISLAND, H. C., RANSON, M., SMITH, R. P., LEADBETTER, J., LAIGHT, A., MCKILLOP, D. and WILD, M. J., 2004, Pharmacokinetic drug interactions with gefitinib, a selective epidermal growth factor receptor tyrosine kinase inhibitor. Clinical Pharmacokinetics (in press).
   Google Scholar
• Tocco, D. J., DUNCAN, A. E. W., DELUNA, F. A., SMITH, J. L., WALKER, R. W. and VANDENHEUVEL, W. J. A., 1980, Timolol metabolism in man and laboratory animals. Drug Metabolism and Disposition, 8, 236–240.
   Google Scholar
• WAKELING, A. E., BARKER, A. J., DAVIES, D. H., BROWN, D. S., GREEN, L. R., CARTLIDGE, S. A. and WOODBURN, J. R., 1997, New targets for therapeutic attack. Endocrine-related Cancer, 4, 351–355.
   Web of Science ®Google Scholar
• WAKELING, A. E., GUY, S. P., WOODBURN, J. R., ASHTON, S. E., CURRY, B. J., BARKER, A. J. and GIBSON, K. H., 2002, ZD1839 (Iressa): an orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy. Cancer Research, 62, 5749–5754.
   PubMed Web of Science ®Google Scholar
• WOODBURN, J. R., 1999, The epidermal growth factor receptor and its inhibition in cancer therapy. Pharmacology and Therapeutics, 82, 241–250.
   PubMed Web of Science ®Google Scholar