Hepatotoxicity of ketoconazole in Sprague-Dawley rats: glutathione depletion, flavin-containing monooxygenases-mediated bioactivation and hepatic covalent binding

References

• BACK, D. J., THA, J. F. and ABEL, S. M., 1992, Azoles, allylamines and drug metabolism. British Journal of Dermatology, 126, 14–18.
   PubMed Web of Science ®Google Scholar
• BAXTER, J. G., BRASS, C., SCHENTAG, J. J. and SLAUGHTER, R. L., 1986, Pharmacokinetics of ketoconazole administered intravenously to dogs and orally as tablet and solution to humans and dogs. Journal of Pharmaceutical Sciences, 75, 443–447.
   PubMedGoogle Scholar
• BENSON, G. D., ANDERSON, P. K., COMBES, B. and IsuAx, K. G., 1988, Prolonged jaundice following ketoconazole-induced hepatic injury. Digestive Diseases Sciences, 33, 240–246.
   PubMed Web of Science ®Google Scholar
• BERCOFF, E., BERNUAU, J., DEGOTT, C., KALIS, B., LAMAIRE, A., TILLY, H., RUEFF, B. and BENHAMOU, J. P., 1985, Ketoconazole-induced fulminant hepatitis. Gut, 26, 636–638.
   PubMed Web of Science ®Google Scholar
• Box, R. A. and SMALL, E. J., 1999, The treatment of advanced prostate cancer with ketoconazole: safety issues. Drug Safety, 20, 451–458.
   PubMedGoogle Scholar
• BRASS, C., GALGIANI, J. N., BLASCHKE, T. F., DEFELICE, R., O'REILLy, R. A. and STEVENS, D. A., 1982, Disposition of ketoconazole, an oral antifungal, in humans. Antimicrobial Agents and Chemotherapy, 21, 151–158.
   Google Scholar
• BRUSKO, C. S. and MARTEN, J. T., 1991, Ketoconazole hepatotoxicity in a patient treated for environmental illness and systemic candidiasis. Annals of Pharmacotherapy, 25, 1321–1325.
   Google Scholar
• CASHMAN, J. R., XIONG, Y. N., XU, L. and JANOWSKY, A., 1999, N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (Form 3): role in bioactivation and detoxication. Journal of Pharmacology and Experimental Therapeutics, 288, 1251–1260.
   PubMed Web of Science ®Google Scholar
• CAUWENBERGH, G., 1989, Safety aspects of ketoconazole, the most commonly used systemic antifungal. Mycoses, 32, 59–63.
   PubMed Web of Science ®Google Scholar
• CHIEN, R.-N., YANG, L.-J., LIN, P.-Y. and LIAW, Y.-F., 1997, Hepatic injury during ketoconazole therapy in patients with onychomycosis: a controlled cohort study. Hepatology, 25, 103–107.
   Google Scholar
• DANESHMEND, T. K. and WARNOCK, D. W., 1988, Clinical pharmacokinetics of ketoconazole. Clinical Pharmacokinetics, 14, 13–34.
   PubMed Web of Science ®Google Scholar
• DANESHMEND, T. K., WARNOCK, D. W., ENE, M. D., JOHNSON, E. M. and PARKER, G., 1983, Multiple dose pharmacokinetics of ketoconazole and their effects on antipyrine kinetics in man. Journal of Antimicrobics and Chemotheraphy, 12, 185–188.
   PubMed Web of Science ®Google Scholar
• DE COSTER, R., CAERS, I., COENE, M. C., AMERY, W., BEERENS, D. and HAELTERMAN, C., 1986, Effects of high dose ketoconazole therapy on the main plasma testicular and adrenal steroids in previously untreated prostatic cancer patients. Clinical Endocrinology, 24, 657–664.
   PubMedGoogle Scholar
• DE COSTER, R., WOUTERS, W. and BRUYNESEELS, J., 1996, P450-dependent enzymes as targets for prostate cancer therapy. Journal of Steroid Biochemical and Molecular Biology, 56, 133–143.
   PubMedGoogle Scholar
• DUARTE, P. A., CHOW, C. C., SIMMONS, F. and RUSKIN, J., 1984, Fatal hepatitis associated with ketoconazole therapy. Archives of Internal Medicine, 144, 1069–1070.
   PubMedGoogle Scholar
• GASCOIGNE, E. W., BARTON, G. J., MICHAELS, M., MEULDERMANS, W. and HEYKANTS, J., 1981, The kinetics of ketoconazole in animals and man. Clinical Research Reviews, 1, 177–187.
   Google Scholar
• GRADON, J. D. and SEPKOWITZ, D. V., 1990, Massive hepatic enlargement with fatty change associated with ketoconazole. Annals of Pharmacotherapy, 24, 1175–1176.
   Google Scholar
• HEEL, R. C., BROGDEN, R. N., CARMINE, A., MORLEY, P. A., SPEIGHT, T. M. and AVERY, G. S., 1982, Ketoconazole: a review of its therapeutic efficacy in superficial and systemic fungal infections. Drugs, 23, 1–36.
   PubMed Web of Science ®Google Scholar
• HOGBERG, J. and KRISTOFERSON, A., 1977, A correlation between glutathione levels and cellular damage in isolated hepatocytes. European Journal of Biochemistry, 74, 77–82.
   PubMedGoogle Scholar
• HUANG, Y. C., COLAIZZI, J. L., BIERMAN, R. H., WOESTENBORGHS, R. and HEYKANTS, J., 1986, Pharmacokinetics and dose proportionality of ketoconazole in normal volunteers. Antimicrobial Agents and Chemotheraphy, 30, 206–210.
   PubMed Web of Science ®Google Scholar
• HT, Research Institute, 1999, Chemoprevention—prostate cancer. Life Sciences Newsletter, Fall, 2–4.
   Google Scholar
• JAcoBs, P. H. and NAL L., 1988, The action and safety of ketoconazole: a brief literature review. CUTIS, 42, 276–282.
   PubMedGoogle Scholar
• JAEGER, R. J., CONOLLY, R. B. and MURPHY, S. D., 1973, Diurnal variation of hepatic glutathione concentration and its correlation with 1,1-dichloroethylene inhalation toxicity in rats. Research Communication in Chemical Pathology and Pharmacology, 6, 465–471.
   PubMedGoogle Scholar
• JANSSEN, 1995, Product monograph: Nizoral®, Ketoconazole (Titusville, NJ: Janssen Pharmaceuticals). JANSSEN, P. A. and SYMOENS, J. E., 1983, Hepatic reactions during ketoconazole treatment. American Journal of Medicine, 74, 80–85.
   Google Scholar
• KNIGHT, T. E., SHIKUMA, C. Y. and KNIGHT, J., 1991, Ketoconazole-induced fulminant hepatitis necessitating liver transplantation. Journal of the American Academy of Dermatology, 25, 398–400.
   PubMedGoogle Scholar
• KUROKOHCHI, K., NisHioxA, M. and IcHixAwA, Y., 1992, Inhibition mechanism of reconstituted cytochrome P-450s cc-linked monooxygenase system by antimycotic reagents and other inhibitors. Journal of Steroid Biochemistry and Molecular Biology, 42, 287–292.
   PubMed Web of Science ®Google Scholar
• LEWIS, J. H., ZIMMERMAN, H. J., BENSON, G. D. and ISHAK, K. G., 1984, Hepatic injury associated with ketoconazole therapy. Gastroenterology, 86, 503–513.
   PubMed Web of Science ®Google Scholar
• MACNAIR, A. L., GASCOIGNE, E., HEAP, J., SCHUEMAN, V. and SYMOENS, J., 1981, Hepatitis and ketoconazole therapy. British Medical Journal, 283, 1058–1059.
   PubMed Web of Science ®Google Scholar
• ROBERTS, J. C. and FRANCETIC, D. J., 1993, The importance of sample preparation and storage in glutathione analysis. Analytical Biochemistry, 211, 183–187.
   PubMed Web of Science ®Google Scholar
• RODRIGUES, A. D., GIBSON, G. G., IONNIDES, C. and PARKE, D. V., 1987a, Interactions of imidazole antifungal agents with purified cytochrome P-450 proteins. Biochemical Pharmacology, 36, 4277–4281.
   PubMed Web of Science ®Google Scholar
• RODRIGUES, A. D., LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1987b, Spectral and kinetic studies of the interaction of imidazole anti-fungal agents with microsomal cytochrome P-450. Xenobiotica, 17, 1315–1327.
   Google Scholar
• RODRIGUEZ, R. J. and ACOSTA, D., 1997a, N-deacetyl ketoconazole-induced hepatotoxicity in a primary culture system of rat hepatocytes. Toxicology, 117, 123–131.
   PubMed Web of Science ®Google Scholar
• RODRIGUEZ, R. J. and ACOSTA, D., 1997b, Metabolism of ketoconazole and deacetylated ketoconazole by rat hepatic microsomes and fiavin-containing monooxygenases. Drug Metabolism and Disposition, 25, 772–777.
   PubMed Web of Science ®Google Scholar
• RODRIGUEZ, R. J., PROTEAU, P. J., MARQUEZ, B., HETHERINGTON, C. L., BucKHoLz, C. J. and O'CONNELL, K. L., 1999, Flavin-containing monooxygenase-mediated metabolism of N-deacetyl ketoconazole by rat hepatic microsomes. Drug Metabolism and Disposition, 27, 880–886.
   Google Scholar
• STRICKER, B. H. C., BLOK, A. P. R., BRONKHORST, F. B., VAN PARYS, G. E. and DESMET, V. J., 1986, Ketoconazole-associated hepatic injury a clinicopathological study of 55 cases. Journal of Hepatology, 3, 399–406.
   Google Scholar
• SUGAR, A. M., ALSIP, S. G., GALGIANI, J. N., GRAYBILL, J. R., DISMUKES, W. E., CLOUD, G. A., CRAVEN, P. C. and STEVENS, D. A., 1987, Pharmacology and toxicity of high-dose ketoconazole. Antimicrobial Agents and Chemotheraphy, 31, 1874–1878.
   PubMed Web of Science ®Google Scholar
• SVEJGAARD, E. and RANEK, L., 1982, Hepatic dysfunction and ketoconazole therapy. Annals of Internal Medicine, 96, 788–789.
   PubMed Web of Science ®Google Scholar
• VAN PARYS, G., EVENEPOEL, C., VAN DAMME, B. and DESMET, V. J., 1987, Ketoconazole-induced hepatitis: a case with a definite cause-effect relationship. Liver, 7, 27–30.
   PubMedGoogle Scholar
• VANDEN BOSSCHE, H., MARICHAL, P., GORRENS, J., GEERTS, J. and JANSSEN, P. A., 1988, Basis for the search for new antifungal drugs. Annals of the New York Academy of Sciences, 544,191–207.
   PubMedGoogle Scholar
• WHITEHOUSE., L. W., MENZIES, A., DAWSON, B., ZAMECNIK, J. and Sy, W. W., 1990, Deacetylated ketoconazole: a major ketoconazole metabolite isolated from mouse liver. Journal of Pharmaceutical Biomedical Analysis, 8, 603–606.
   PubMed Web of Science ®Google Scholar
• ZIEGLER, D. M., 1980, Microsomal fiavin-containing monoxygenase: oxygenation of nucleophilic nitrogen and sulfur compounds. Enzymatic Basis of Detoxication, 1,201–227.
   Google Scholar
• ZIEGLER, D. M., 1988. Flavin-containing monooxygenases: catalytic mechanism and substrate specificities. Drug Metabolism Reviews, 19, 1–32.
   PubMed Web of Science ®Google Scholar