Contribution of itraconazole metabolites to inhibition of CYP3A4 in vivo

Clinical Pharmacology and Therapeutics

Volumn 83, Issue 1, 2008, Pages 77-85

  Templeton, I E ^a   Thummel, K E ^a   Kharasch, E D ^a,b   Kunze, K L ^a   Hoffer, C ^b   Nelson, W L ^a   Isoherranen, N ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A4; HYDROXY ITRACONAZOLE; ITRACONAZOLE; KETO ITRACONAZOLE; UNCLASSIFIED DRUG;

ADULT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG STRUCTURE; FEMALE; HUMAN; HUMAN EXPERIMENT; LIVER MICROSOME; MALE; MAXIMUM PLASMA CONCENTRATION; NORMAL HUMAN; PREDICTION; PRIORITY JOURNAL; STEADY STATE;

ADMINISTRATION, ORAL; ADULT; ANTIFUNGAL AGENTS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; ENZYME INHIBITORS; FEMALE; GLUCURONIDES; HUMANS; ITRACONAZOLE; LIVER; MALE; MODELS, BIOLOGICAL;

EID: 37549070318     PISSN: 00099236     EISSN: 15326535     Source Type: Journal    
DOI: 10.1038/sj.clpt.6100230     Document Type: Article

References (35)

1. Haria, M., Bryson, H.M. & Goa, K.L. Itraconazole. A reappraisal of its pharmacological properties and therapeutic use in the management of superficial fungal infections. Drugs 51, 585-620 (1996).
2. Poirier, J.M. & Cheymol, G. Optimisation of itraconazole therapy using target drug concentrations. Clin. Pharmacokinet. 35, 461-473 (1998).
3. Barone, J.A. et al. Enhanced bioavailability of itraconazole in hydroxypropyl-beta-cyclodextrin solution versus capsules in healthy volunteers. Antimicrob. Agents Chemother. 42, 1862-1865 (1998).
4. Hardin, T.C. et al. Pharmacokinetics of itraconazole following oral administration to normal volunteers. Antimicrob. Agents Chemother. 32, 1310-1313 (1988).
5. Schäfer-Körting, M. Pharmacokinetic optimisation of oral antifungal therapy. Clin. Pharmacokinet. 25, 329-341 (1993).
6. Heykants, J. et al. The clinical pharmacokinetics of itraconazole: an overview. Mycoses 32(Suppl 1): 67-87 (1989).
7. Barone, J.A. et al. Food interaction and steady-state pharmacokinetics of itraconazole capsules in healthy male volunteers. Antimicrob. Agents Chemother. 37, 778-784 (1993).
8. Isoherranen, N., Kunze, K.L., Allen, K.E., Nelson, W.L. & Thummel, K.E. Role of itraconazole metabolites in CYP3A inhibition. Drug Metab. Dispos. 32, 1121-1131 (2004).
9. Neuvonen, P.J., Kantola, T. & Kivisto, K.T. Simvastatin but not pravastatin is very susceptible to interaction with the CYP3A4 inhibitor itraconazole. Clin. Pharmacol. Ther. 63, 332-341 (1998).
10. Olkkola, K.T., Ahonen, J. & Neuvonen, P.J. The effect of systemic antimycotics itraconazole and fluconazole on the pharmacokinetics and pharmacodynamics of intravenous and oral midazolam. Anesth. Analg. 82, 511-516 (1996).
11. Backman, J.T., Kivisto, K.T., Olkkola, K.T. & Neuvonen, P.J. The area under the plasma concentration-time curve for oral midazolam is 400-fold larger during treatment with itraconazole than with rifampicin. Eur. J. Clin. Pharmacol. 54, 53-58 (1998).
12. Florea, N.R., Capitano, B., Nightingale, C.H., Hull, D., Leitz, G.J. & Nicolau, D.P. Beneficial pharmacokinetic interaction between cyclosporine and itraconazole in renal transplant recipients. Transplant. Proc. 35, 2873-2877 (2003).
13. Mahnke, C.B. et al. Tacrolimus dosage requirements after initiation of azole antifungal therapy in pediatric thoracic organ transplantation. Pediatr. Transplant. 7, 474-478 (2003).
14. Yamano, K., Yamamoto, K., Kotaki, H., Sawada, Y. & Iga, T. Quantitative prediction of metabolic inhibition of midazolam by itraconazole and ketoconazole in rats: implication of concentrative uptake of inhibitors into liver. Drug Metab. Dispos. 27, 395-402 (1999).
15. Yamano, K. et al. Prediction of midazolam-CYP3A inhibitors interaction in the human liver from in vivo/in vitro absorption, distribution, and metabolism data. Drug Metab. Dispos. 29, 443-452 (2001).
16. Galetin, A., Ito, K., Hallifax, D. & Houston, J.B. CYP3A4 substrate selection and substitutions in the prediction of potential drug-drug interactions. J. Pharmacol. Exp. Ther. 314, 180-190 (2005).
17. Heykants, J. et al. The pharmacokinetics of itraconazole in animals and man: an overview In Recent Trends in the Discovery, Development, and Evaluation of Antifungal Agents (ed. Fromtling, R.A.) pp 223-249 (J.R. Prous Science Publishers, Barcelona, 1987).
18. Meuldermans, W. & Heykants, J. The plasma protein binding of itraconazole and its distribution in blood. Janssen Pharmaceutica Preclinical Research Report R51211/33 (FDA/CDER Rockville, MD, 1986).
19. Rowland, M. & Tozer, T.N. Clinical Pharmacokinetics: Concepts and Applications 3rd edn. (Lippincott Williams & Wilkins, Philadelphia, 1995).
20. Gibaldi, M. & Perrier, D. Pharmacokinetics 2nd edn. (Marcel Dekker Inc., New York, 1982).
21. Banerjee, R., Leaver, N., Lyster, H. & Banner, N.R. Coadministration of itraconazole and tacrolimus after thoracic organ transplantation. Transplant. Proc. 33, 1600-1602 (2001).
22. Kwan, J.T., Foxall, P.J., Davidson, D.G., Bending, M.R. & Eisinger, A.J. Interaction of cyclosporin and itraconazole. Lancet 2, 282 (1987).
23. Yasui, N. et al. Effect of itraconazole on the single oral dose pharmacokinetics and pharmacodynamics of alprazolam. Psychopharmacology 139, 269-273 (1998).
24. Pearson, J.T. et al. Surface plasmon resonance analysis of antifungal azoles binding to CYP3A4 with kinetic resolution of multiple binding orientations. Biochemistry 45, 6341-6353 (2006).
25. Breadmore, M.C. & Thormann, W. Capillary electrophoresis evidence for the stereoselective metabolism of itraconazole in man. Electrophoresis 24, 2588-2597 (2003).
26. Kunze, K.L., Nelson, W.L., Kharasch, E.D., Thummel, K.E. & Isoherranen, N. Stereochemical aspects of itraconazole metabolism in vitro and in vivo. Drug Metab. Dispos. 34, 583-590 (2006).
27. Ghosal, A. et al. Identification of human UDP- glucuronosyltransferase enzyme(s) responsible for the glucuronidation of posaconazole (Noxafil). Drug Metab. Dispos. 32, 267-271 (2004).
28. Krieter, P. et al. Disposition of posaconazole following single-dose oral administration in healthy subjects. Antimicrob. Agents Chemother. 48, 3543-3551 (2004).
29. Heeres, J., Backx, L.J. & Van Cutsem, J. Antimycotic azoles 7 Synthesis and antifungal properties of a series of novel triazol-3-ones. J. Med. Chem. 27, 894-900 (1984).
30. Nakai, D., Kumamoto, K., Sakikawa, C., Kosaka, T. & Tokui, T. Evaluation of the protein binding ratio of drugs by a micro-scale ultracentrifugation method. J. Pharm. Sci. 93, 847-854 (2004).
31. Brunton, L.L., Lazo, J.S. & Parker, K.L. Goodman and Gilman's The Pharmacological Basis of Therapeutics 11th edn. (McGraw-Hill, New York, 2006).
32. Trouvin, J.H. et al. Pharmacokinetics of midazolam in anaesthetized cirrhotic patients. Br. J. Anaesth. 60, 762-767 (1988).
33. Rowland, M. & Matin, S.B. Kinetics of drug-drug interactions. J. Pharm. Bio. 1, 553-568 (1973).
34. Wang, Y.-H., Jones, D.R. & Hall, S.D. Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab. Dispos. 32, 259-266 (2004).
35. Webb, J.L. Enzyme and Metabolic Inhibitors. (Academic Press, New York, 1963).