Metabolism-based drug interactions involving oral azole antifungals in humans

Drug Metabolism Reviews

Volumn 31, Issue 3, 1999, Pages 665-717

  Benedetti, M Strolin ^a   Bani, M ^b,c  

^a UCB PHARMA   (Belgium)

^b Zambon Group SpA   (Italy)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIALLERGIC AGENT; ANTIASTHMATIC AGENT; ANTIBIOTIC AGENT; ANTICOAGULANT AGENT; ANTIDIABETIC AGENT; ANTIFUNGAL AGENT; ANTIHYPERTENSIVE AGENT; ANTINEOPLASTIC AGENT; ANTIPROTOZOAL AGENT; BUSULFAN; CARDIOVASCULAR AGENT; CISAPRIDE; CYCLOSPORIN; DIGOXIN; FLUCONAZOLE; FLUCYTOSINE; GLIBENCLAMIDE; IMMUNOSUPPRESSIVE AGENT; ITRACONAZOLE; KETOCONAZOLE; NIFEDIPINE; OMEPRAZOLE; OXYBUTYNIN; QUINIDINE; RIFAMPICIN; TERFENADINE; THEOPHYLLINE; TOLBUTAMIDE; UNINDEXED DRUG; WARFARIN;

ALLERGY; ANTIBIOTIC THERAPY; ARTICLE; ASTHMA; AUTOIMMUNE DISEASE; BACTERIAL INFECTION; CANCER; CANCER CHEMOTHERAPY; CARDIOVASCULAR DISEASE; DIABETES MELLITUS; DRUG METABOLISM; GASTROINTESTINAL DISEASE; HUMAN; HYPERTENSION; IMMUNOSUPPRESSIVE TREATMENT; MYCOSIS; ORAL DRUG ADMINISTRATION; PROTOZOAL INFECTION; URINE INCONTINENCE;

ADJUVANTS, IMMUNOLOGIC; ANTI-ASTHMATIC AGENTS; ANTI-INFECTIVE AGENTS; ANTICOAGULANTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIPROTOZOAL AGENTS; AZOLES; CARDIOVASCULAR AGENTS; CENTRAL NERVOUS SYSTEM AGENTS; DRUG INTERACTIONS; GASTROINTESTINAL AGENTS; HUMANS; HYPOGLYCEMIC AGENTS; RENAL AGENTS;

EID: 0032796389     PISSN: 03602532     EISSN: None     Source Type: Journal    
DOI: 10.1081/DMR-100101941     Document Type: Article

References (177)

1. H. Vanden Bossche, Biochemical targets for antifungal azole derivatives: Hypotesis on the mode of action, Curr. Topics Med. Mycol., 9, 321-356 (1983).
2. C. G. Meredith, A. L. Maldonado, and K. V. Speeg, The effect of ketoconazole on hepatic oxidative drug metabolism in the rat in vivo and in vitro, Drug Metab. Disp., 13, 156-162 (1985).
3. P. Mosca, P. Bonazzi, G. Novelli, A. M. Jezequel, and F. Orlandi, In vivo and in vitro inhibition of hepatic microsomal drug metabolism by ketoconazole, Ar. J. Exp, Pathol., 66, 737-742 (1985).
4. K. Lavrijsen, J. Van Houdt, D. Thijs, W. Meuldermans, and J. Heykants, Induction potential of antifungals containing an imidazole or triazole moiety, Biochem. Pharmacol., 35, 1867-1878 (1986).
5. I. La Delfa, Q. M. Zhu, Z. Mo, and T. F. Blaschke, Fluconazole is a potent inhibitor of antipyrine metabolism in vivo in mice, Drug Metab. Disp., 17, 49-53 (1989).
6. K. Lavrijsen, J. Van Houdt, M. Van Dyck, W. Meuldermans, and J. Heykants, Induction potential of fluconazole toward drug-metabolizing enzymes in rats, Antimicrob. Agents Chemother., 34, 402-408 (1990).
7. J. A. Como and W. E. Dismukes, Oral azole drugs as systemic antifungal therapy, N. Engl. J. Med., 330, 263-272 (1994).
8. M. Maurice, L. Pichard, M. Daujat, et al., Effect of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture, FASEB J., 6, 752-758 (1992).
9. Ketoconazole, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
10. Fluconazole, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
11. Itraconazole, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
12. P. F. Troke, R. J. Andrews, and G. W. Pye, Fluconazole and other azoles: Translation of in vitro activity to in vivo and clinical efficacy, Rev. Infect. Dis., 12, 276-280 (1990).
13. J. H. Lin and A. Y. H. Lu, Role of pharmacokinetics and metabolism in drug discovery and development, Pharmacol. Rev., 49, 403-449 (1997).
14. J. A. Barone, J. G. Kohl, R. H. Bierman, et al., Food interaction and steady-state pharmacokinetics of itraconazole capsules in healthy male volunteers, Antimicrob. Agents Chemother., 37, 778-784 (1993).
15. R. M. Ferguson, D. Sutherland, R. L. Simmons, and J. S. Najarian, Ketoconazole, cyclosporin metabolism, and renal transplantation, Lancet, 2(8303), 882-883 (1982).
16. H. Dieperink and J. Moller, Ketoconazole and cyclosporin, Lancet, 2(8309), 1217 (1982).
17. C. Cunningham, M. D. Burke, P. H. Whiting, J. G. Simpson, and D. N. Wheatley, Ketoconazole, cyclosporin, and the kidney, Lancet, 2(8313), 1464 (1982).
18. T. K. Daneshmend and D. W. Warnock, Clinical pharmacokinetics of ketoconazole, Clin. Pharmacokin., 14, 13-34 (1988).
19. D. Y. Gomez, V. J. Wacher, S. J. Tomlanovic, M. F. Hebert, and L. Z. Benet, The effect of ketoconazole on the intestinal metabolism and bioavailability of cyclosporine, Clin. Pharm. Ther., 58, 15-19 (1995).
20. K. S. Lown, R. R. Mayo, A. B. Leichtman, et al., Role of intestinal P-glycoprotein in interpatient variation in the oral bioavailability of cyclosporine, Clin. Pharm. Ther., 62, 248-260 (1997).
21. O. Odocha, B. Kelly, S. Trimble, C. Murigande, R. M. Toussaint, and C. O. Callander, Cost-containment strategies in transplantation: The utility of cyclosporine-ketoconazole combination therapy, Transplant. Proc., 28, 907-909 (1996).
22. S. M. Grant and S. P. Clissold, Fluconazole: a review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in superficial and systemic mycoses, Drugs, 39, 877-916 (1990).
23. K. L. Goa and L. B. Barradell, Fluconazole: An update of its pharmacodynamic and pharmacokinetic properties and therapeutic use in major superficial and systemic mycoses in immunocompromised patients, Drugs, 50, 658-690 (1995).
24. A. M. Sugar, C. Saunders, B. A. Idelson, and D. B. Bernard, Interaction of fluconazole and cyclosporine, Ann. Intern. Med., 110, 844 (1989).
25. P. Collignon, B. Hurley, and D. Mitchel, Interaction of fluconazole with cyclosporin, Lancet, 1 (8649), 1262 (1989).
26. J. D. Lazar and K. D. Wilner, Drug interactions with fluconazole, Rev. Infect. Dis., 12, S327-S333 (1990).
27. H. U. Krüger, U. Schuler, R. Zimmerman, and G. Ehninger, No severe drug interaction of fluconazole, a triazole antifungal agent, with cyclosporin, Bone Marrow Transpl., 3(Suppl. 1), 271 (1988).
28. J. T. C. Kwan, P. J. D. Foxall, D. G. C. Davidson, M. R. Bending, and A. J. Eisinger, Interaction with cyclosporin and itraconazole, Lancet, 2(8553), 282 (1987).
29. D. Trenk, W. Brett, E. Jhanchen, and D. Birnbaum, Time course of cyclosporin/itraconazole interaction, Lancet, 2(8571), 1335-1336 (1987).
30. I. Novakova, P. Donnelly, T. De Witte, B. De Pauw, J. Boezeman, and G. Veltman, Itraconazole and cyclosporin nephrotoxicity, Lancet, 2(8564), 20 (1987).
31. M. R. Kramer, Dose adjustment and cost of itraconazole prophylaxis in lung transplant recipients receiving cyclosporine and tacrolimus (FK506), Transplant. Proc., 29, 2657-2659 (1997).
32. L. C. Floren, I. Bekersky, L. Z. Benet, et al., Tacrolimus oral bioavailability doubles with coadministration of ketoconazole, Clin. Pharm. Ther., 62, 41-49 (1997).
33. 14C-busulfan in isolated perfused rat liver, Eur. J. Drug Pharmacokinet., 17, 71 (1987).
34. N. Hassan and H. Erhsson, Urine metabolites of busulfan in the rat, Drug Metab. Disp., 16, 1856 (1988).
35. D. H. Marchand, R. P. Remmel, and M. M. Abdel-Monem, Biliary excretion of glutathione conjugate of busulfan and 1,4-diiodobutane in the rat, Drug Metab. Disp., 16, 85-92 (1993).
36. G. Vassal, I. Boland, A. Deroussent, D. Georgin, and A. Gouyette, In vitro busulfan metabolism in human and mouse liver, Proc. Am. Assoc. Cancer Res., 34, 2995 (1994).
37. I. Buggia, M. Zecca, E. P. Alessandrino, et al., Itraconazole can increase systemic exposure to busulfan in patients given bone marrow transplantation, Anticancer Res., 16, 2083-2088 (1996).
38. E. Spina, A. Avenoso, G. M. Campo, M. G. Scordo, A. P. Caputi, and E. Perucca, Effect of ketoconazole on the pharmacokinetics of imipramine and desipramine in healthy subject, Br. J. Clin. Pharmacol., 43, 315-318 (1997).
39. P. Ghahramani, S. W. Ellis, M. S. Lennard, L. E. Ramsay, and G. T. Tucker, Cytochromes P-450 mediating the N-demethylation of amitripty-line, Br. J. Clin. Pharmacol., 43, 137-144 (1997).
40. Nortriptyline, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
41. D. L. Newberry, S. N. Bass, and C. O. Mbanefo, A fluconazole/amitripty-line drug interaction in three male adults, Clin. Infect. Dis., 24, 270-271 (1997).
42. R. H. Gannon and N. L. Anderson, Fluconazole-nortriptyline drug interaction, Ann. Pharmacother., 26, 1456-1457 (1992).
43. T. Kronbach, D. Mathys, M. Umeno, F. J. Gonzales, and U. A. Meyer, Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4, Mol. Pharmacol. 36, 89-96 (1989).
44. K. T. Olkkola, J. T. Backman, and P. J. Neuvonen, Midazolam should be avoided in patients receiving the systemic antimycotics ketoconazole or itraconazole, Clin. Pharmacol. Ther., 55, 481-485 (1994).
45. J. Ahonen, K. T. Olkkola, and P. J. Neuvonen, Effect of route of administration of fluconazole on the interaction between fluconazole and midazolam, Eur. J. Clin. Pharmacol., 51, 415-419 (1997).
46. J. Ahonen, K. T. Olkkola, and P. J. Neuvonen, Effect of itraconazole and terbinafine on the pharmacokinetics and pharmacodynamics of midazolam in healthy volunteers, Br. J. Clin. Pharmacol., 40, 270-272 (1995).
47. L. L. Von Moltke, D. J. Greenblatt, J. S. Harmatz, et al., Triazolam biotransformation by human liver microsomes in vitro: Effects of metabolic inhibitors and clinical confirmation of a predicted interaction with ketoconazole, J. Pharmacol. Exp. Ther., 276, 370-379 (1996).
48. A. Varh, K. T. Olkkola, and P. J. Neuvonen, Oral triazolam is potentially hazardous to patients receiving systemic antimycotics ketoconazole or itraconazole, Clin. Pharmacol. Ther., 56, 601-607 (1994).
49. C. E. Wright, D. J. Greenblatt, L. L. von Moltke, B. L. Ehrenberg, J. S. Harmatz, and K. Corbett, Ketoconazole inhibition of triazolam and alprazolam clearance: Differential kinetic and dynamic consequences, Clin. Pharmacol. Ther., 61, 183, PII-71 (1997).
50. A. Varhe, K. T. Olkkola, and P. J. Neuvonen, Fluconazole, but not terbinafine, enhances the effects of triazolam by inhibiting its metabolism, Br. J. Clin. Pharmacol., 41, 319-323 (1996).
51. A. Varhe, K. T. Olkkola, and P. J. Neuvonen, Effect of fluconazole dose on the extent of fluconazole-triazolam interaction, Br. J. Clin. Pharmacol., 42, 465-470 (1996).
52. P. J. Neuvonen, A. Varhe, and K. T. Olkkola, The effect of ingestion time interval on the interaction between itraconazole and triazolam, Clin. Pharmacol. Ther., 60, 326-331 (1996).
53. M. W. Brown, A. L. Maldonado, C. G. Meredith, and K. V. Speeg, Effect of ketoconazole on hepatic oxidative drug metabolism, Clin. Pharmacol. Ther., 37, 290-297 (1985).
54. K. T. Kivisto, T. S. Lamberg, T. Kantola, and P. J. Neuvonen, Plasma buspirone concentration are greatly increased by erythromycin and itraconazole, Clin. Pharmacol. Ther., 62, 348-354 (1997).
55. K. Villikka, K. T. Kivisto, T. S. Lamberg, T. Kantola, and P. J. Neuvonen, Concentrations and effects of zoplicone are greatly reduced by rifampicin, Br. J. Clin. Pharmacol., 43, 471-474 (1997).
56. K. M. Jalava, K. T. Olkkola, and P. J. Neuvonen, The effect of itraconazole on the pharmacokinetics and pharmacodynamics of zopiclone, Exp. Toxicol. Pathol., 48, 357 (1996).
57. K. M. Jalava, K. T. Olkkola, and P. J. Neuvonen, Effect of itraconazole on the pharmacokinetics and pharmacodynamics of zopiclone, Eur. J. Clin. Pharmacol., 51, 331-334 (1996).
58. H. Luurila, K. T. Kivisto, and P. J. Neuvonen, Effect of itraconazole on the pharmacokinetics and pharmacodynamics of zolpidem, Eur. J. Clin. Pharmacol., 54, 163-166 (1998).
59. M. Strolin Benedetti and P. Dostert, Contribution of amine oxidases to the metabolism of xenobiotics, Drug Metab. Rev., 26, 507-535 (1994).
60. L. P. Pan, P. Wijnant, G. De Vriendt, M. T. Rosseel, and F. M. Belpaire, Characterization of the cytochrome P-450 isoenzymes involved in the in vitro N-dealkylation of haloperidol, Br. J. Clin. Pharmacol., 44, 557-564 (1997).
61. T. Ohnuma, N. Iwamoto, N. Arai, et al., A case who had increased plasma-concentrations of haloperidol during itraconazole-treatment, Seishin Igaku, 38, 865-867 (1996).
62. K. Raaska and P. J. Neuvonen, Serum concentrations of clozapine and N-desmethylclozapine are unaffected by the potent CYP3A4 inhibitor itraconazole, Eur. J. Clin. Pharmacol., 54, 167-170 (1998).
63. R. Riva, F. Albani, M. Contin, and A. Baruzzi, Pharmacokinetic interactions between antiepileptic drugs, Clin. Pharmacokinet., 31, 470-493 (1996).
64. J. Schmider, D. J. Greenblatt, L. L. von Moltke, D. Karsov, and R. I. Shader, Inhibition of CYP2C9 by selective serotonin reuptake inhibitors in vitro: Studies of phenytoin p-hydroxylation, Br. J. Clin. Pharmacol., 44, 495-498 (1997).
65. M. A. Touchette, P. H. Chandrasekar, M. Milad, and D. J. Edwards, Contrasting effects of fluconazole and ketoconazole on phenytoin and testosterone disposition in man, Br. J. Clin. Pharmacol., 34, 75-78 (1992).
66. A. S. Mitchell and J. T. Holland, Fluconazole and phenytoin: A predictable interaction, Br. Med. J., 298, 1315 (1989).
67. J. D. Lazar and K. D. Wilner, Drug interactions with fluconazole, Rev. Infect. Dis., 12, S327-S333 (1990).
68. A. R. Blum, J. H. Wilton, D. M. Hilligoss, et al., Effect of fluconazole on the disposition of phenytoin, Clin. Pharmacol. Ther., 49, 420-425 (1991).
69. M. P. Ducharme, R. L. Slaughter, L. H. Warbasse, et al., Itraconazole and hydroxyitraconazole serum concentrations are reduced more than tenfold by phenytoin, Clin. Pharmacol. Ther., 58, 617-624 (1995).
70. J. O. Atiba, T. F. Blaschke, and G. R. Wilkinson, Effects of ketoconazole on the polymorphic 4-hydroxylations of S-mephenytoin and debrisoquine, Br. J. Clin. Pharmacol., 28, 161-165 (1989).
71. F. P. Guengerich, W. R. Brian, M. Iwasaki, M. A. Sari, C. Bäärnhielm, and P. Berntsson, Oxidation of dihydropyrine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4, J. Med. Chem., 34, 1838-1844 (1991).
72. S. A. N. Tailor, A. K. Gupta, S. E. Walker, and N. H. Shea, Peripheral edema due to nifedipine-itraconazole interaction: A case report, Arch. Dermatol., 132, 350-352 (1996).
73. K. M. Jalava, K. T. Olkkola, and P. J. Neuvonen, Itraconazole greatly increases plasma concentrations and effects of felodipine, Clin. Pharmacol. Ther., 61, 410-415 (1997).
74. Digoxin, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
75. C. A. Kauffman and F. K. Bagnasco, Digoxin toxicity associated with itraconazole therapy, Clin. Infect. Dis., 15, 886-887 (1992).
76. J. Rex, Itraconazole-digoxin interaction, Ann. Intern. Med., 116, 525 (1992).
77. M. K. Sachs, L. D. Blanchard, and P. J. Green, Interaction of itraconazole and digoxin, Clin. Infect. Dis., 16, 400-403 (1993).
78. K. L. McClean and G. J. Sheehan, Interaction between itraconazole and digoxin, Clin. Infect. Dis., 18, 259-260 (1994).
79. C. P. Alderman and P. D. Allcroft, Digoxin interaction, Ann. Pharmacother., 31, 438-440 (1997).
80. K. M. Jalava, J. Partanen, and P. J. Neuvonen, Digoxin + itraconazole: Drug interaction, Therapie, 50, S185 (1995).
81. S. Antila, M. Karisson, L. Lehtonen, T. Honkanen, and P. J. Neuvonen, Effect of itraconazole on pharmacokinetics of the calcium-sensitizing drug levosimendan, Therapie, 50, S460 (1995).
82. P. J. Neuvonen and K. M. Jalava, Itraconazole drastically increases plasma concentrations of lovastatin and lovastatin acid, Clin. Pharmacol. Ther., 60, 54-61 (1996).
83. R. S. Lees and A. M. Less, Rhabdomyolysis from the coadministration of lovastatin and the antifungal agent itraconazole, N. Engl. J. Med., 333, 664 (1995).
84. T. Prueksaritanont, L. M. Gorham, M. A. Bennet, et al., In vitro metabolism of simvastatin in humans: Identification of metabolizing enzymes and effect of the drug on hepatic P450S, Drug Metab. Disp., 5, 1191-1199 (1997).
85. Lovastatin, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
86. Simvastatin, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
87. N. Horn, Coadministration of itraconazole with hypolipidemic agents may induce rhabdomyolysis in healthy individuals, Arch. Dermatol., 132, 1254 (1996).
88. N. F. Segaert, C. De Soete, I. Vanderwiele, and J. Verbanck, Drug-interaction-induced rhabdomyolysis, Nephrol. Dialysis Transplant, 11, 1846-1847 (1996).
89. P. J. Neuvonen, T. Kantola, and K. T. Kivistö, Simvastatin but not pravastatin is very susceptible to interaction with the CYP3A4 inhibitor itraconazole, Clin. Pharm. Ther., 63, 332-341 (1998).
90. Z. Abolfathi, H. Pakdel, P. Beaune, and J. Turgeon, CYP1A2 is the major involved N-oxidation of mexiletine in man, Clin. Pharmacol. Ther., 57, 215 (1995).
91. K. Ueno, R. Yamaguchi, and K. Tanaka, Lack of kinetic interaction between fluconazole and mexiletine, Eur. J. Clin. Pharmacol., 50, 129-131 (1996).
92. K. L. Kunze, L. C. Wienkers, K. E. Thummel, and W. F. Trager, Warfarin-fluconazole I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: In vitro studies, Drug Metab. Disp., 24, 414-421 (1996).
93. R. A. Stearns, P. K. Chakravarty, R. Chen, and S. H. Lee Chiu, Biotransformation of losartan to its active carboxylic acid metabolite in human liver microsomes, Drug Metab. Disp., 23, 207-215 (1995).
94. J. B. McCrea, M. W. Lo, C. I. Furtek, et al., Ketoconazole does not effect the systemic conversion of losartan to E-3174, Clin. Pharmacol. Ther., 59, 169, PII-44 (1994).
95. D. J. Kazierad, D. E. Martin, R. A. Blum, et al., Effect of fluconazole on the pharmacokinetics of eprosartan and losartan in healthy male volunteers, Clin. Pharmacol. Ther., 62, 417-425 (1997).
96. E. Lukkari, A. Juhakoski, K. Aranko, and P. J. Neuvonen, Itraconazole moderately increases serum concentrations of oxybutynin but does not affect those of the active metabolite, Eur. J. Clin. Pharmacol., 52, 403-406 (1997).
97. Y. Böttiger, G. Tybring, E. Götharson, and L. Bertilsson, Inhibition of the sulfoxidation of omeprazole by ketoconazole in poor and extensive metabolizers of S-mephenytoin, Clin. Pharmacol. Ther., 62, 384-391 (1997).
98. S. R. Ahmad and S. M. Wolfe, Cisapride and torsades de pointes, Lancet 345, 312 (1995).
99. N. H. Chan-Thompkins and T. J. Babinchak, Cardiac arrhythmias associated with coadministration of azole compound and cisapride, Clin. Infect. Dis., 24, 1285 (1997).
100. D. K. Wysowski and J. Bacsanyi, Cisapride and fatal arrhythmia, N. Engl. J. Med., 335, 290-291 (1996).
101. H. Yamazaki and T. Shimada, Human liver cytochrome P450 enzymes involved in the 7-hydroxylation of R-and S-warfarin enantiomers, Biochem. Pharmacol., 54, 1195-1203 (1997).
102. C. Brass, J. N. Galgiani, T. F. Blaschke, R. Defelice, R. A. O'Reilly, and D. A. Stevens, Disposition of ketoconazole, an oral antifungal, in humans, Antimicrob. Agents Chem., 21, 151-158 (1982).
103. A. G. Smith, Potentiation of oral anticoagulants by ketoconazole, Br. Med. J., 288, 188 (1984).
104. D. J. Black, K. L. Kunze, L. C. Wienkers, and B. E. Gidal, Warfarin-fluconazole II. A metabolically based drug interaction: In vitro studies, Drug Metab. Disp., 24, 422-428 (1996).
105. J. Yeh, S. C. Soo, C. T. Summerton, and C. Richardson, Potentiation of action of warfarin by itraconazole, Br. Med. J., 301, 669 (1990).
106. M. Haria, H. M. Bryson, and K. L. Goa, Itraconazole, Drugs, 51, 585-620 (1996).
107. Nicoumalone, in Therapeutic Drugs (C. T. Dollery, ed.), Churchill Livingstone, Edinburgh, 1991.
108. B. J. Isalska and T. N. Stanbridge, Fluconazole in the treatment of candidal prosthetic valve endocarditis, Br. Med. J., 297, 178-179 (1988).
109. M. E. Veronese, P. I. Mackenzie, C. J. Doecke, M. E. McManus, J. O. Miners, and D. J. Birkett, Tolbutamide and phenytoin hydroxylations by cDNA-expressed human liver cytochrome P4502C9, Biochem. Biophys. Res. Commun., 175, 1112-1118 (1991).
110. M. E. Veronese, J. O. Miners, D. Randles, D. Gregov, and D. J. Birkett, Validation of the tolbutamide metabolic ratio for population screening with use of sulfaphenazole to produce model phenotypic poor metabolizers, Clin. Pharmacol. Ther., 47, 403-411 (1990).
111. Y. S. R. Krishnaiah, S. Satyanarayana, and D. Visweswaram, Interaction between tolbutamide and ketoconazole in healthy subjects, Br. J. Clin. Pharmacol., 37, 205-207 (1994).
112. D. J. Back, J. F. Tjia, J. Karbwang, and J. Colbert, In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines, Br. J. Clin. Pharmacol., 26, 23-29 (1988).
113. D. J. Back, P. Stevenson, and J. F. Tjia, Comparative effects of two antimycotic agents, ketoconazole and terbinafine on the metabolism of tolbutamide, ethinyloestetradiol, cyclosporin and ethoxycoumarin by human liver microsomes in vitro, Br. J. Clin. Pharmacol., 28, 166-170 (1989).
114. K. L. Kunze and W. F. Trager, Warfarin-fluconazole III. A rational approach to management of a metabolically based drug interaction, Drug Metab. Disp., 24, 429-435 (1996).
115. J. P. Fournier, S. Schneider, P. Martinez, et al., Coma hypoglycémique chez une patiente traitée par glipizide et fluconazole: Une possible interaction? Therapie, 47, 433-447 (1992).
116. J. D. Lazar and K. D. Wilner, Key drug interaction studies with fluconazole, Conference Abs. Canada, 1989.
117. 4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes, Drug Metab. Disp., 23, 406-414 (1995).
118. H. J. Gill, J. L. Maggs, S. Madden, M. Pirmohamed, and B. K. Park, The effect of fluconazole and ketoconazole on the metabolism of sulphamethoxazole, Br. J. Clin. Pharmacol., 42, 347-353 (1996).
119. A. K. Mitra, E. T. Kenneth, T. F. Kalhorn, E. D. Kharasch, and J. D. Unadkat, Inhibition of sulfamethoxazole hydroxylamine formation by fluconazole in human liver microsomes and healthy volunteers, Clin. Pharmacol. Ther., 59, 332-340 (1996).
120. M. Strolin Benedetti, Inducing properties of rifabutin, and effects on the pharmacokinetics and metabolism of concomitant drugs, Pharmacol. Res., 32, 177-187 (1995).
121. B. Reinach, G. de Sousa, P. Dostert, B. Ings, J. Gugenheim, and R. Rahmani, Effect of rifabutin on cytochromes P450 and glucoronosyl-transferases activities in human hepatocyte cultures, ISSX Proc., 11, 172 (1997).
122. G. Cocchiara, M. Strolin Benedetti, G. P. Vicario, et al., Urinary metabolites of rifabutin, a new antimycobacterial agent, in human volunteers, Xenobiotica, 19, 769-780 (1989).
123. I. Utkin, T. Koudriakova, T. Thompson, et al., Isolation and identification of major urinary metabolites of rifabutin in rats and humans, Drug Metab. Disp., 25, 963-969 (1997).
124. C. B. Trapnell, C. Jamis-Dow, R. W. Klecker, and J. M. Collins, Metabolism of rifabutin and its 25-desacetyl metabolite, LM565, by human liver microsomes and recombinant human cytochrome P-450 3A4: Relevance to clinical interaction with fluconazole, Antimicrob. Agents Chem., 41, 924-926 (1997).
125. M. Strolin Benedetti, C. Efthymiopoulos, D. Sassella, E. Moro, and M. Repetto, Autoinduction of rifabutin metabolism in man, Xenobiotica, 20, 1113-1119 (1990).
126. C. B. Trapnell, P. K. Nrang, R. Li, et al., Fluconazole increases rifabutin (RIF) absorption in HIV (+) patients on stable zidovudine (ZDV) therapy, Proc. 9th Int. Conf. AIDS, Berlin, 1993, p. 504.
127. C. B. Trapnell, P. K. Nrang, R. Li, and J. P. Lavelle, Increased plasma rifabutin levels with concomitant fluconazole therapy in HIV-infected patients, Ann. Intern. Med., 124, 573-576 (1996).
128. P. K. Narang, C. B. Trapnell, J. R. Schoenfelder, J. P. Lavelle, and J. R. Bianchine, Fluconazole and enhanced effect of rifabutin prophylaxis, N. Engl. J. Med., 330, 1316-1317 (1995).
129. J. Gioulekas and A. Hall, Uveitis associated with rifabutin therapy, J. Ophtalmol., 23, 319-321 (1995).
130. A. Lefort, O. Launay, and C. Carbon, Uveitis associated with rifabutin prophylaxis and itraconazole therapy, Ann. Intern. Med., 125, 939-940 (1996).
131. M. Strolin Benedetti and P. Dostert, Induction and autoinduction properties of rifamycin derivatives: A review of animal and human studies, Environ. Health Perspect, 102, 101-105 (1994).
132. D. Engelhard, H. R. Stutman, and M. I. Marks, Interaction of ketoconazole with rifampin and isoniazid, N. Engl. J. Med., 311, 1681-1683 (1996).
133. S. Jaruratanasirikul and A. Kleepkaew, Lack of effect of fluconazole on the pharmacokinetics of rifampicin in AIDS patients, J. Antimicrob. Chem., 38, 877-880 (1996).
134. G. N. Kumar, A. D. Rodrigues, A. M. Buko, and J. F. Denissen, Cytochrome P450-mediated metabolism of the HIV protease inhibitor ritonavir (ABT-538) in human liver microsomes, J. Pharmacol. Exp. Ther., 277, 423-431 (1996).
135. A. Cato III, G. Cao, A. Hsu, J. Cavanaugh, J. Leonard, and R. Granneman, Evaluation of the effect of fluconazole on the pharmacokinetics of ritonavir, Drug Metab. Disp., 25, 1104-1106 (1997).
136. J. McCrea, E. Woolf, A. Sterrett, et al., Effects of ketoconazole and other P-450 inhibitors on the pharmacokinetics of indinavir, Pharm. Res., 13, S485 (1996).
137. J. Sahai, K. Gallicano, A. Pakuts, and D. W. Cameron, Effect of fluconazole on zidovudine pharmacokinetics in patients infected with human immunodeficiency virus, J. Infect. Dis., 169, 1103-1107 (1994).
138. S. A. Bozzette, R. A. Larsen, J. Chiu, et al., A placebo controlled trial of maintenance therapy with fluconazole after treatment of cryptococcal mengitis in the acquired immunodeficiency syndrome, N. Engl. J. Med., 324, 580-584 (1991).
139. C. A. Knupp, D. C. Brate, J. Relue, and R. H. Barbhaiya, Pharmacokinetics of didanosine ketoconazole after coadministration to patients seropositive for the human immunodeficiency virus, J. Clin. Pharmacol., 33, 912-917 (1993).
140. V. L. Bruzzese, J. G. Gillum, D. S. Israel, G. L. Jhonson, L. G. Kaplowitz, and R. E. Polk, Effect of fluconazole on pharmacokinetics of 2′,3′-dideoxynosine in persons seropositive for human immunodeficiency virus, Antimicrob. Agents Chem., 39, 1050-1053 (1995).
141. R. M. McNulty, J. A. Lazor, and M. Sketch, Transient increase in plasma quinidine concentrations during ketoconazole-quinidine therapy, Clin. Pharmacol., 8, 222-225 (1989).
142. K. M. Kaukonen, K. T. Olkkola, and P. J. Neuvonen, Itraconazole increases plasma concentrations of quinidine. Clin. Pharmacol. Ther., 62, 510-517 (1997).
143. C. H. Yun, R. A. Okerholm, and F. P. Guengerich, Oxidation of the antihistaminic drug terfenadine in human liver microsomes, role of cytochrome P450 3A(4) in N-dealkylation and C-hydroxylation, Drug Metab. Disp., 21, 403-409 (1993).
144. K. J. Ling, G. A. Leeson, S. D. Burmaster, R. H. Hook, M. K. Reith, and L. K. Cheng, Metabolism of terfenadine associated with CYP3A4 activity in human hepatic microsomes, Drug Metab. Disp., 23, 631-636 (1995).
145. A. P. Li, Drug-drug interactions: Scientific and regulatory perspectives, Adv. Pharmacol., 43, 103-130 (1997).
146. P. K. Honig, D. C. Wortham, K. Zamani, D. P. Conner, J. C. Mullin, and L. R. Cantilena, Terfenadine-ketoconazole interaction, J. Am. Med. Assoc., 269, 1513-1518 (1993).
147. G. A. Burkhart, M. J. Sevka, R. Temple, and P. K. Honig, Pharmacoepidemiology and drug utilization, Clin. Pharmacol. Ther., 61, 93-96 (1997).
148. P. K. Honig, D. C. Wortham, K. Zamani, J. C. Mullin, D. P. Conner, and L. R. Cantilena, The effect of fluconazole on the steady-state pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine in humans, Clin. Pharmacol Ther., 53, 630-636 (1993).
149. S. Pohjola-Sintonen, M. Viitasalo, L. Toivonen, and P. Neuvonen, Itraconazole prevent terfenadine metabolism and increases risk of torsades de pointes ventricular tachycardia, Eur. J. Clin. Pharmacol., 45, 191-193 (1993).
150. P. K. Honig, D. C. Wortham, R. Hull, K. Zamani, J. E. Smith, and L. R. Cantilena, Itraconazole affects single-dose terfenadine pharmacokinetics and cardiac repolarization pharmacodynamics, J. Clin. Pharmacol., 33, 1201-1206 (1993).
151. A. Markham and A. J. Wagstaff, Fexofenadine, Drugs, 55, 269-274 (1998).
152. 1-receptor-antagonist drugs, N. Engl. J. Med., 330, 1664-1670 (1994).
153. 14C-cetirizine in humans, Ann. Allergy, 59, 31-34 (1987).
154. Cetirizine challenges other antihistamines in allergic rhinitis and chronic idiopathic urticaria, Drugs Ther. Perspect., 5(8), 1-4 (1994).
155. N. A. Von Rosenstiel and D. Adam, Macrolide antibacterials. Drug interactions of clinical significance, Drug Safety, 13, 105-122 (1995).
156. R. A. Lefebvre, A. Van Peer, and R. Woestenborghs, Influence of itraconazole on the pharmacokinetics and electrocardiographic effects of astemizole, Br. J. Clin. Pharmacol., 43, 319-322 (1997).
157. K. Lavrijsen, J. Van Houdt, W. Meuldermans, M. Janssens, and J. Heykants, The interaction of ketoconazole, itraconazole and erythromycin with the in vitro metabolism of antihistamines in human liver microsomes, Allergy, 48, 34 (1993).
158. A. P. D'Mello, M. J. D'Souza, and T. R. Bates, Pharmacokinetics of ketoconazole-antipyrine interaction, Lancet, 2(8448), 209-210 (1985).
159. T. K. Daneshmend, D. W. Warnock, M. D. Ene, et al., Multiple dose pharmacokinetics of ketoconazole and their effects on antipyrine kinetics in man, J. Antimicrob. Chemother., 12, 185-188 (1983).
160. R. C. Dockens, D. Rapoport, D. Roberts, D. S. Greene, and R. H. Barbhaiya, Lack of an effect of nefazodone on the pharmacokinetics and pharmacodynamics of theophylline during concurrent administration in patients with chronic obstructive pulmonary disease, Br. J. Clin. Pharmacol., 40, 598-601 (1995).
161. B. B. Rasmussen and K. Brosen, Theophylline has no advantages over caffeine as a putative model drug for assessing CYPIA2 activity in humans, Br. J. Clin. Pharmacol., 43, 253-258 (1997).
162. H. Konishi, K. Monta, and A. Yamaji, Effect of fluconazole on theophylline disposition in humans, Eur. J. Clin. Pharmacol., 46, 309-312 (1994).
163. D. McKillop, C. J. Butters, S. J. Hill, P. J. Simons, T. L. Edwards, and S. E. Doughty, Enzyme-inducing effects of bicalutamide in mouse, rat and dog, Xenobiotica, 28, 465-478 (1998).
164. F. Thalhammer, U. M. Hollenstein, G. J. Locker, et al., Azithromycin-related toxic effects of digitoxin, Br. J. Clin. Pharmacol., 45, 91-92 (1998).
165. B. D. Alexander and J. A. Perfect, Antifungal resistance trends towards the year 2000, Drugs, 54, 657-678 (1997).
166. J. O. Miners and D. J. Birkett, Cytochrome P4502C9: An enzyme of major importance in human drug metabolism, Br. J. Clin. Pharmacol., 45, 525-538 (1998).
167. L. Salphati and L. Z. Benet, Effect of ketoconazole on digoxin absorption and disposition in rat, Pharmacology, 56, 308-313 (1998).
168. J. D. Chan, Pharmacokinetic drug interactions of vinca alkaloids: Summary of case reports. Pharmacotherapeutics, 18, 1304-1307 (1998).
169. Y. Chang, Y. Hsieh, T. Izumi, and L. Z. Benet, Effects of ketoconazole on the intestinal metabolism, transport and oral bioavailability of K02, a novel vinylsulfone peptidomimetic cysteine protease inhibitor and a P450 3A, P-glycoprotein dual substrate, in male SD rats, J. Pharm. Exp. Ther., 287, 246-252 (1998).
170. M. D. Coleman, A. K. Scott, A. M. Breckenridge, and B. K. Park, The use of cimetidine as a selective inhibitor of dapsone N-hydroxylation in man, Br. J. Clin. Pharmacol., 30, 761-767 (1990).
171. M. D. Coleman, L. E. Rhodes, A. K. Scott, et al., The use of cimetidine to reduce dapsone-dependent methaemoglobinaemia in dermatitis herpetiformis, Br. J. Clin. Pharmacol., 34, 244-249 (1992).
172. L. E. Rhodes, M. D. Tingle, B. K. Park, P. Chu, J. L. Verbov, and P. S. Friedmann, Cimetidine improves the therapeutic/toxic ratio of dapsone in patients on chronic dapsone therapy, Br. J. Dermatol., 132, 257-262 (1995).
173. J. A. Hargreaves, S. Jezequel, and J. B. Houston, Effect of azole antifungals on human microsomal metabolism of diclofenac and midazolam, Br. J. Clin. Pharmacol., 38, 175P (1994).
174. T. Leemann, C. Transon, and P. Dayer, Cytochrome P450TB (CYP2C): A major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver, Life Sci., 52, 29-34 (1993).
175. A. Mancy, P. Broto, S. Dijols, P. M. Dansette, and D. Mansuy, The substrate binding site of human liver cytochrome P450 2C9: An approach using designed tienilic acid derivatives and molecular modeling, Biochemistry, 34, 10,365-10,375 (1995).
176. E. S. Tomlinson, J. L. Maggs, B. K. Park, and D. J. Back, Dexamethasone metabolism in vitro: Species differences in 6-hydroxylation, Br. J. Clin. Pharmacol., 41, 462-463P (1996).
177. L. Pichard, I. Fabre, G. Fabre, et al., Cyclosporin and drug interactions, Drug Metab. Disp., 18, 595-606 (1990).