Effects of the antifungals voriconazole and fluconazole on the pharmacokinetics of S-(+)- and R-(-)-ibuprofen

Antimicrobial Agents and Chemotherapy

Volumn 50, Issue 6, 2006, Pages 1967-1972

  Hynninen, Ville Veikko ^a,d   Olkkola, Klaus T ^a   Leino, Kari ^a   Lundgren, Stefan ^b   Neuvonen, Pertti J ^c   Rane, Anders ^b   Valtonen, Mika ^a   Vyyryläinen, Hanna ^c   Laine, Kari ^a  

^a TURKU UNIVERSITY HOSPITAL   (Finland)

^b KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^c UNIVERSITY OF HELSINKI   (Finland)

^d UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CYTOCHROME P450 2C9; FLUCONAZOL; FLUCONAZOLE; IBUPROFEN; VORICONAZOLE;

ADULT; ANALGESIC NEPHROPATHY; AREA UNDER THE CURVE; ARTICLE; BIOEQUIVALENCE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CROSSOVER PROCEDURE; DRUG BLOOD LEVEL; DRUG DOSE REDUCTION; DRUG EFFECT; DRUG HALF LIFE; DRUG MEGADOSE; DRUG METABOLISM; ENZYME INHIBITION; FLUID RETENTION; GASTRITIS; HUMAN; INTESTINAL BLEEDING; MALE; NORMAL HUMAN; PEPTIC ULCER; PRIORITY JOURNAL; RACEMIC MIXTURE; RANDOMIZED CONTROLLED TRIAL; SIDE EFFECT; SINGLE DRUG DOSE;

ADULT; ANALGESICS, NON-NARCOTIC; ANTIFUNGAL AGENTS; AREA UNDER CURVE; CROSS-OVER STUDIES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG ADMINISTRATION SCHEDULE; DRUG INTERACTIONS; FLUCONAZOLE; HALF-LIFE; HUMANS; IBUPROFEN; MALE; PYRIMIDINES; THERAPEUTIC EQUIVALENCY; TRIAZOLES;

EID: 33744500482     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.01483-05     Document Type: Article

References (35)

1. Adams, S. S., P. Bresloff, and C. G. Mason. 1976. Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer. J. Pharm. Pharmacol. 28:256-257.
2. Avgerinos, A., and A. J. Hutt. 1990. Interindividual variability in the enantiomeric disposition of ibuprofen following the oral administration of the racemic drug to healthy volunteers. Chirality 2:249-256.
3. Back, D. J., J. F. Tjia, J. Karbwang, and J. Colbert. 1988. In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines. Br. J. Clin. Pharmacol. 26:23-29.
4. Black, D. J., K. L. Kunze, L. C. Wienkers, B. E. Gidal, T. L. Seaton, N. D. McDonnell, J. S. Evans, J. E. Bauwens, and W. F. Trager. 1996. Warfarin-fluconazole. II. A metabolically based drug interaction: in vivo studies. Drug Metab. Dispos. 24:422-428.
5. Cuenca-Estrella, M., J. L. Rodriguez-Tudela, E. Mellado, J. V. Martinez-Suarez, and A. Monzon. 1998. Comparison of the in-vitro activity of voriconazole (UK-109,496), itraconazole and amphotericin B against clinical isolates of Aspergillus fumigatus. J. Antimicrob. Chemother. 42:531-533.
6. Dai, D., D. C. Zeldin, J. A. Blaisdell, B. Chanas, S. J. Coulter, B. I. Ghanayem, and J. A. Goldstein. 2001. Polymorphisms in human CYP2C8 decrease metabolism of the anticancer drug paclitaxel and arachidonic acid. Pharmacogenetics 11:597-607.
7. Davies, N. M., A. J. McLachlan, R. O. Day, and K. M. Williams. 2000. Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin. Pharmacokinet. 38:225-242.
8. Espinel-Ingroff, A. 1998. In vitro activity of the new triazole voriconazole (UK-109.496) against opportunistic filamentous and dimorphic fungi and common and emerging yeast pathogens. J. Clin. Microbiol. 36:198-202.
9. Evans, A. M. 1992. Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs. Eur. J. Clin. Pharmacol. 42:237-256.
10. Gage, R., and D. A. Stopher. 1998. A rapid HPLC assay for voriconazole in human plasma. J. Pharm. Biomed. Anal. 17:1449-1453.
11. Garcia-Martin, E., C. Martinez, B. Tabares, J. Frias, and J. A. Agundez. 2004. Interindividual variability in ibuprofen pharmacokinetics is related to interaction of cytochrome P450 2C8 and 2C9 amino acid polymorphisms. Clin. Pharmacol. Ther. 76:119-127.
12. Hamman, M. A., G. A. Thompson, and S. D. Hall. 1997. Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. Biochem. Pharmacol. 54:33-41.
13. Hyland, R., B. C. Jones, and D. A. Smith. 2003. Identification of the cytochrome P450 enzymes involved in the N-oxidation of voriconazole. Drug Metab. Dispos. 31:540-547.
14. Ikeda, Y., K. Umemura, K. Kondo, K. Sekiguchi, S. Miyoshi, and M. Nakashima. 2004. Pharmacokinetics of voriconazole and cytochrome P450 2C19 genetic status. Clin. Pharmacol. Ther. 75:587-588.
15. Inagaki, K., J. Takagi, E. Lor, M. P. Okamoto, and M. A. Gill. 1992. Determination of fluconazole in human serum by solid-phase extraction and reversed-phase high-performance liquid chromatography. Ther. Drug Monit. 14:306-311.
16. Kaiser, D. G., G. J. Vangiessen, R. J. Reischer, and W. J. Wechter. 1976. Isomeric inversion of ibuprofen (R)-enantiomer in humans. J. Pharm. Sci. 65:269-273.
17. Kang, B. C., C. Q. Yang, H. K. Cho, O. K. Suh, and W. G. Shin. 2002. Influence of fluconazole on the pharmacokinetics of omeprazole in healthy volunteers. Biopharm. Drug Dispos. 23:77-81.
18. Kaukonen, K. M., K. T. Olkkola, and P. J. Neuvonen. 1998. Fluconazole but not itraconazole decreases the metabolism of losartan to E-3174. Eur. J. Clin. Pharmacol. 53:445-449.
19. Kirchheiner, J., I. Meineke, G. Freytag, C. Meisel, I. Roots, and J. Brockmoller. 2002. Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofen pharmacokinetics and on the inhibition of cyclooxygenases 1 and 2. Clin. Pharmacol. Ther. 72:62-75.
20. Kunze, K. L., L. C. Wienkers, K. E. Thummel, and W. F. Trager. 1996. Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab. Dispos. 24:414-421.
21. Martinez, C., G. Blanco, J. M. Ladero, E. Garcia-Martin, C. Taxonera, F. G. Gamito, M. Diaz-Rubio, and J. A. Agundez. 2004. Genetic predisposition to acute gastrointestinal bleeding after NSAIDs use. Br. J. Pharmacol. 141:205-208.
22. Menzel-Soglowek, S., G. Geisslinger, and K. Brune. 1990. Stereoselective high-performance liquid chromatographic determination of ketoprofen, ibuprofen and fenoprofen in plasma using a chiral alpha 1-acid glycoprotein column. J. Chromatogr. 532:295-303.
23. Morita, K., H. Konishi, and H. Shimakawa. 1992. Fluconazole: a potent inhibitor of cytochrome P-450-dependent drug-metabolism in mice and humans in vivo. Comparative study with ketoconazole. Chem. Pharm. Bull. (Tokyo) 40:1247-1251.
24. Niemi, M., J. T. Backman, L. I. Kajosaari, J. B. Leathart, M. Neuvonen, A. K. Daly, M. Eichelbaum, K. T. Kivistö, and P. J. Neuvonen. 2005. Polymorphic organic anion transporting polypeptide 1B1 is a major determinant of repaglinide pharmacokinetics. Clin. Pharmacol. Ther. 77:468-478.
25. Pennick, G. J., M. Clark, D. A. Sutton, and M. G. Rinaldi. 2003. Development and validation of a high-performance liquid chromatography assay for voriconazole. Antimicrob. Agents Chemother. 47:2348-2350.
26. Pettersson, K. J., and A. Olsson. 1991. Liquid chromatographic determination of the enantiomers of ibuprofen in plasma using a chiral AGP column. J. Chromatogr. 563:414-418.
27. Pfaller, M. A., J. Zhang, S. A. Messer, M. E. Brandt, R. A. Hajjeh, C. J. Jessup, M. Tumberland, E. K. Mbidde, and M. A. Ghannoum. 1999. In vitro activities of voriconazole, fluconazole, and itraconazole against 566 clinical isolates of Cryptococcus neoformans from the United States and Africa. Antimicrob. Agents Chemother. 43:169-171.
28. Purkins, L., N. Wood, D. Kleinermans, and D. Nichols. 2003. Voriconazole potentiates warfarin-induced prothrombin time prolongation. Br. J. Clin. Pharmacol. 56(Suppl. 1):24-29.
29. Purkins, L., N. Wood, K. Greenhalgh, M. J. Allen, and S. D. Oliver. 2003. Voriconazole, a novel wide-spectrum triazole: oral pharmacokinetics and safety. Br. J. Clin. Pharmacol. 56(Suppl. 1):10-16.
30. Purkins, L., N. Wood, P. Ghahramani, E. R. Love, M. D. Eve, and A. Fielding. 2003. Coadministration of voriconazole and phenytoin: pharmacokinetic interaction, safety, and toleration. Br. J. Clin. Pharmacol. 56(Suppl. 1):37-44.
31. Romero, A. J., P. L. Pogamp, L. G. Nilsson, and N. Wood. 2002. Effect of voriconazole on the pharmacokinetics of cyclosporine in renal transplant patients. Clin. Pharmacol. Ther. 71:226-234.
32. Scott, G., L. Yih, C. M. Yeh, S. Milosavljev, A. Laurent, and C. Rordorf. 2004. Lumiracoxib: pharmacokinetic and pharmacodynamic profile when coadministered with fluconazole in healthy subjects. J. Clin. Pharmacol. 44:193-199.
33. Walsky, R. L., E. A. Gaman, and R. S. Obach. 2005. Examination of 209 drugs for inhibition of cytochrome P450 2C8. J. Clin. Pharmacol. 45:68-78.
34. Wienkers, L. C., C. J. Wurden, E. Storch, K. L. Kunze, A. E. Rettie, and W. F. Trager. 1996. Formation of (R)-8-hydroxywarfarin in human liver microsomes. A new metabolic marker for the (S)-mephenytoin hydroxylase, P4502C19. Drug Metab. Dispos. 24:610-614.
35. Xie, H. G., H. C. Prasad, R. B. Kim, and C. M. Stein. 2002. CYP2C9 allelic variants: ethnic distribution and functional significance. Adv. Drug Deliv. Rev. 54:1257-1270.