Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 3
204
Views
222
CrossRef citations to date
0
Altmetric
Original Article

Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9

, , , , &
Pages 261-270 | Received 14 Oct 1994, Published online: 27 Aug 2009

References

  • Abel S. M., Back D. J. Cortisol metabolism in vitro. III. Inhibition of microsomal 6β-hydroxylase and cytosolic 4-ene-reductase. Journal of Steroid Biochemistry and Molecular Biology 1993; 46: 827–832
  • Back D. J., Park B. K., Tjia J. F., Newby S. N. Sulphaphenazole and drug oxidation in man. British Journal of Clinical Pharmacology 1983; 16: 460–461
  • Back D. J., Stevenson P., Tjia J. F. Comparative effects of two antimycotic agents ketoconazole and terbinafine on the metabolism of tolbutamide, ethinyloestradiol, cycloporine and ethoxycoumarin by human liver microsomes in vitro. British Journal of Clinical Pharmacology 1989; 28: 166–170
  • Back D. J., Tjia J. F., Abel S. M. Azoles, allylamines and drug metabolism. British Journal of Dermatology 1992; 126: 14–18
  • Back D. J., Tjia J. F., Karbwang J., Colbert J. In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines. British Journal of Clinical Pharmacology 1988; 26: 23–29
  • Berthou F., Flinois J.-P., Ratanasavanh D., Beaune P., Riche C., Guillouzo A. Evidence for the involvement of several cytochromes P-450 in the steps of caffeine metabolism by human liver microsomes. Drug Metabolism and Disposition 1991; 19: 561–567
  • Brian W. R., Srivastava P. K., Umbenhauer D. R., Lloyd R. S., Guengerich F. P. Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in. Saccharomyces cerevisiae. Biochemistry 1989; 28: 4993–4999
  • Brown M. W., Meredith C. G., Maldonado A. L., Speeg K. V. Ketoconazole inhibition of oxidative drug metabolism: effect of age and gender. Clinical Research 1983; 31: 883–891
  • Burke M. D., Thompson S., Elcombe C. R., Halpert J., Haaparanta T., Mayer R. T. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochemical Pharmacology 1985; 34: 3337–3345
  • Cambell M. E., Grant D. M., Inaba T., Kalow W. Biotransformation of caffeine, paraxanthine, theophylline and theobromine by polycyclic aromatic hydrocarbon-inducible cytochrome(s) P-450 in human liver microsomes. Drug Metabolism and Disposition 1987; 15: 237–249
  • Christensen L. K., Hansen J. M., Kristensen M. Sulphaphenazole-induced hypoglycaemic attacks in tolbutamide-treated diabetes. Lancet 1963; ii: 1298–1301
  • Clarke S. E., Ayrton A. D., Chenery R. J. Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica 1994; 24: 517–526
  • Clarke S. E., Baldwin S. J., Bloomer J. C., Ayrton A. D., Sozio R. S., Chenery R. J. Lauric acid as a model substrate for the simultaneous determination of cytochrome P450 2E1 and 4A in hepatic microsomes. Chemical Research in Toxicology 1994a; 7: 836–842
  • Combalbert J., Fabre I., Fabre G., Dalet I., Derancourt J., Cano J. P., Maurel P. Metabolism of cyclosporin A. Purification and identification of the rifampicin-inducible human liver cytochrome P-450 (cyclosporine A oxidase) as a product of P450IIIA gene subfamily. Drug Metabolism and Disposition 1989; 17: 197–207
  • Daneshmend T. K., Warnock D. W. Clinical pharmacokinetics of ketoconazole. Clinical Pharmacokinetics 1988; 14: 13–34
  • Deluca J. G., Dysart G. R., Ranick D., Bradley M. O. A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarin analog. Biochemical Pharmacology 1988; 37: 1731–1739
  • Dirvn H. A. A. M., Peters J. G. P., Gibson G. G., Peters W. H. M., Jongeneelen F. J. Lauric acid hydroxylase activity and cytochrome P450 IV family proteins in human liver microsomes. Biochemical Pharmacology 1991; 42: 1841–1844
  • Doecke C. J., Veronese M. E., Pond S. M., Miners J. O., Birkett D. J., Sansom L. N., McManus M. E. Relationship between phenytoin and tolbutamide hydroxylations in human liver microsomes. British Journal of Clinical Pharmacology 1991; 31: 125–130
  • Fabre G., Julian B., Saint-Aubert B., Joyeux H., Berger Y. Evidence of CYP3A-mediated N-deethylation of amiodarone in human liver microsomal fractions. Drug Metabolism and Disposition 1993; 21: 978–985
  • Ferguson R. M., Sutherland D. E. R., Simmons R. L., Najarian J. S. Ketoconazole, cyclosporin metabolism and renal transplantation. Lancet 1982; ii: 882–883
  • First M. R., Schroeder T. J., Michael A., Hariharan S., Weiskittel P., Alexander J. W. Cyclosporine-ketoconazole interaction. Transplantation 1993; 55: 1000–1004
  • Funae Y., Imaoka S. Purification and characterization of liver microsomal cytochrome P-450 from untreated male rats. Biochimica et Biophysica Acta 1987; 926: 349–358
  • Gascon M. P., Dayer P. In vitro forecasting of drugs which may interfere with the biotransformation of midazolam. European Journal of Clinical Pharmacology 1991; 41: 573–578
  • Gluckman E., Devergie A., Lokiec F., Poirier O., Baumelou A. Nephrotoxicity of cyclosporin A in bone-marrow transplantation. Lancet 1981; ii: 144–145
  • Glynn A. M., Slaughter R. L., Brass C. D., D'Ambrosio R., Jusko W. J. Effects of ketoconazole on methylprednisolone pharmacokinetics and cortisol secretion. Clinical Pharmacology and Therapeutics 1986; 39: 654–659
  • Graybill J. R., Drutz D. J. Ketoconazole: a major innovation for treatment of fungal disease. Archives of International Medicine 1980; 93: 921–923
  • Guengerich F. P. Mechanism-based inactivation of human liver microsomal cytochrome P450 IIIA4 by gestodene. Chemical Research in Toxicology 1990; 3: 363–371
  • Harrell A. W., Wheeler S. M., Pennick M., Clarke S. E., Chenery R. J. Evidence that famciclovir (BRL 42810) and its associated metabolites do not inhibit the 6β-hydroxylation of testosterone in human liver microsomes. Drug Metabolism and Disposition 1993; 21: 18–23
  • Heel R. C., Brogden R. N., Carmine A., Morley P. A., Speight T. M., Avery G. S. Ketoconazole: a review of its therapeutic efficacy in superficial and systematic fungal infections. Drugs 1982; 23: 1–36
  • Leatherbarrow R. J. Granfit Version 3.0. Erithacus Software Ltd., StainesUK 1992
  • Maurice M., Emiliani S., Dalet-Beluche I., Derancourt J., Lange R. Isolation and characterization of a cytochrome P450 of the IIA subfamily from human liver microsomes. European Journal of Biochemistry 1991; 200: 511–517
  • Maurice M., Pichard L., Daujat M., Fabre I., Joyeux H., Domergue J., Maurel P. Effects of imidazole derivatives on cytochrome P450 from human hepatocytes in primary culture. FASEB Journal 1992; 6: 752–758
  • McInnes G. T., Brodie M. J. Drug interactions that matter. A critical reappraisal. Drugs 1988; 36: 83–110
  • Meier U. T., Kronbach T., Meyer U. A. Assay of mephenytoin metabolism in human liver microsomes by high-performance liquid chromatography. Analytical Biochemistry 1985; 151: 286–291
  • Meredith C. G., Maldonado A. L., Speeg J. R. The effect of ketoconazole on hepatic oxidative drug metabolism in the rat in vivo and in vitro. Drug Metabolism and Disposition 1985; 13: 156–162
  • Miners J. O., Smith K. J., Robson R. A., McManus M. E., Veronese M. E., Birkett D. J. Tolbutamide hydroxylation by human liver microsomes, kinetic characterization and relationship to other cytochrome P-450 dependent xenobiotic oxidations. Biochemical Pharmacology 1988; 37: 1137–1144
  • Nelson D. R., Tetsuya K., Waxman D. J., Guengerich F. P., Estabrook R. W., Feyereisen R., Gonzalez F. J., Coon M. J., Gunsalus I. C., Gotoh O., Okuda K., Nebert D. W. The P450 superfamily: update on the new sequences, gene mapping, accession numbers, early trivial names of enzymes and nomenclature. DNA Cell Biology 1993; 12: 1–51
  • Otton S. V., Crewe H. K., Lennard M. S., Tucker G. T., Woods H. F. Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics 1988; 247: 242–247
  • Peter R., Böcker R., Beaune P. H., Iwasaki M., Guengerich F. P., Yang C. S. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. 1990
  • Chemical Research in Toxicology, 3: 566–573
  • Pichard L., Fabre I., Fabre G., Domergue J., Saint Aubert B., Mourad G., Maurel P. Cyclosporin A drug interactions: screening for inducers and inhibitors of cytochrome P450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metabolism and Disposition 1990; 18: 595–606
  • Pond S. M., Birkett D. J., Wade D. N. Mechanisms of inhibition of tolbutamide metabolism: phenylbutazone, oxyphenylbutazone, sulfaphenazole. Clinical Pharmacology and Therapeutics 1977; 22: 573–579
  • Pont A., Williams P. L., Azhar S., Reitz R. E., Bochra C., Smith E. R., Stevens D. A. Ketoconazole blocks testosterone synthesis. Archives of International Medicine 1982; 142: 2137–2140
  • Relling M. V., Aoyama T., Gonzalez F. J., Meyer U. A. Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. Journal of Pharmacology and Experimental Therapeutics 1990; 252: 442–447
  • Robson R. A., Miners J. O., Matthews A. P., Stupans D. M., McManus M. E., Birkett D. J. Characterization of theophylline metabolism by human liver microsomes. Biochemical Pharmacology 1988; 37: 1651–1659
  • Rowland M., Matin S. B., Thiessen J., Karam J. Kinetics of tolbutamide interactions. Drug Interactions, P. L. Morselli, S. N. Cohen, S. Giorattini. Raven, New York 1974; 199–210
  • Sheets J. J., Mason J. I. Ketoconazole: A potent inhibitor of cytochrome P450-dependent drug metabolism in rat liver. Drug Metabolism and Disposition 1984; 12: 603–606
  • Smith P. K., Krohn R. I., Hermanson G. T., Mallia A. K., Gartner F. H., Provenzano M. D., Fujimoto E. K., Goeke N. M., Olson B. J., Klenk C. Measurement of protein using bicinchoninic acid. Analytical Biochemistry 1985; 150: 76–85
  • Sonino N. The use of ketoconazole as an inhibitor of steroid production. New England Journal of Medicine 1987; 317: 812–818
  • Speeg K. V., Meredith C. G., Maldonado A. L. Ketoconazole inhibits hepatic oxidative drug metabolism. Hepatology 1983; 3: 860–861
  • Speirs C. J., Murray S., Boobis A. R., Seddon C. E., Davies D. S. Quinidine and the identification of drugs whose elimination is impaired in subjects classified as poor metabolizers of debrisoquine. British Journal of Clinical Pharmacology 1986; 22: 739–743
  • Veronese M. E., Miners J. O., Randles D., Gregov D., Birkett D. J. Validation of the tolbutamide metabolic ratio for population screening with use of sulfaphenazole to produce model phenotypic poor metabolizers. Clinical Pharmacology and Therapeutics 1990; 47: 403–411
  • Veronese M. E., Doecke C. J., Mackenzie P. I., McManus M. E., Miners J. O., Rees D. L. P., Gasser R., Meyer U. A., Birkett D. J. Site-directed mutation studies of human liver cytochrome P-450 isoenzymes in the CYP2C subfamily. Biochemical Journal 1993; 289: 533–538
  • Waxman D. J., Lapenson D. P., Aoyama T., Gelboin H. V., Gonzalez F. J., Korzekwa K. Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450. Archives of Biochemistry and Biophysics 1991; 290: 160–166
  • Wrighton S. A., Stevens J. C., Becker G. W., Vandenbranden M. Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin 4′-hydroxylation. Archives of Biochemistry and Biophysics 1993; 306: 240–245
  • Yamano S., Tatsuno J., Gonzalez F. J. The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 1990; 29: 1322–1329
  • Zanger U. M., Vilbois F., Hardwich J., Meyer U. A. Absence of hepatic cytochrome P450bufl causes genetically deficient debrisoquine oxidation in man. Biochemistry 1988; 27: 5447–5454
  • Zhou-Pan X.-R., Seree E., Zhou X.-J., Placidi M., Maurel P., Barra Y., Rahmani R. Involvement of human liver cytochrome P450 3A in vinblastine metabolism: drug interactions. Cancer Research 1993; 53: 5121–5126

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.