Saturated metabolism of voriconazole N-oxidation resulting in nonlinearity of pharmacokinetics of voriconazole at clinical doses

Biological and Pharmaceutical Bulletin

Volumn 38, Issue 10, 2015, Pages 1496-1503

  Yamada, Takahiro ^a   Mino, Yasuaki ^a   Yagi, Tatsuya ^a   Naito, Takafumi ^a   Kawakami, Junichi ^a  

^a HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

CYP2C19; Metabolite; N oxidation; Nonlinear pharmacokinetics; Voriconazole

Indexed keywords

CYTOCHROME P450 2C19; NITRIC OXIDE; VORICONAZOLE; ANTIFUNGAL AGENT; CYP2C19 PROTEIN, HUMAN;

ADULT; AGED; ARTICLE; CONTROLLED STUDY; CORRELATION COEFFICIENT; DRUG METABOLISM; DRUG OXIDATION; DRUG SCREENING; FEMALE; GENOTYPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; JAPANESE (PEOPLE); MAJOR CLINICAL STUDY; MALE; METABOLIC RATIO; MIDDLE AGED; MINIMUM PLASMA CONCENTRATION; NONLINEAR SYSTEM; BIOTRANSFORMATION; BLOOD; GENETIC VARIATION; GENETICS; OXIDATION REDUCTION REACTION;

AGED; ANTIFUNGAL AGENTS; BIOTRANSFORMATION; CYTOCHROME P-450 CYP2C19; FEMALE; GENETIC VARIATION; GENOTYPE; HUMANS; MALE; MIDDLE AGED; OXIDATION-REDUCTION; VORICONAZOLE;

EID: 84946906061     PISSN: 09186158     EISSN: 13475215     Source Type: Journal    
DOI: 10.1248/bpb.b15-00241     Document Type: Article

References (29)

1. Pemán J, Salavert M, Cantón E, Jarque I, Romá E, Zaragoza R, Viudes A, Gobernado M. Voriconazole in the management of nosocomial invasive fungal infections. Ther. Clin. Risk Manag., 2, 129-158 (2006).
2. Walsh TJ, Anaissie EJ, Denning DW, Herbrecht R, Kontoyiannis DP, Marr KA, Morrison VA, Segal BH, Steinbach WJ, Stevens DA, van Burik JA, Wingard JR, Patterson TF, Infectious Diseases Society of America. Treatment of aspergillosis: clinical practice guidelines of the Infectious Diseases Society of America. Clin. Infect. Dis., 46, 327-360 (2008).
3. Steinbach WJ, Stevens DA. Review of newer antifungal and immunomodulatory strategies for invasive aspergillosis. Clin. Infect. Dis., 37 (Suppl. 3), S157-S187 (2003).
4. Smith J, Safdar N, Knasinski V, Simmons W, Bhavnani SM, Ambrose PG, Andes D. Voriconazole therapeutic drug monitoring. Antimicrob. Agents Chemother., 50, 1570-1572 (2006).
5. Ueda K, Nannya Y, Kumano K, Hangaishi A, Takahashi T, Imai Y, Kurokawa M. Monitoring trough concentration of voriconazole is important to ensure successful antifungal therapy and to avoid hepatic damage in patients with hematological disorders. Int. J. Hematol., 89, 592-599 (2009).
6. Goodwin ML, Drew RH. Antifungal serum concentration monitoring: an update. J. Antimicrob. Chemother., 61, 17-25 (2008).
7. Miyakis S, van Hal SJ, Ray J, Marriott D. Voriconazole concentrations and outcome of invasive fungal infections. Clin. Microbiol. Infect., 16, 927-933 (2010).
8. Pascual A, Calandra T, Bolay S, Buclin T, Bille J, Marchetti O. Voriconazole therapeutic drug monitoring in patients with invasive mycoses improves efficacy and safety outcomes. Clin. Infect. Dis., 46, 201-211 (2008).
9. Hamada Y, Seto Y, Yago K, Kuroyama M. Investigation and threshold of optimum blood concentration of voriconazole: a descriptive statistical meta-analysis. J. Infect. Chemother., 18, 501-507 (2012).
10. Denning DW, Ribaud P, Milpied N, Caillot D, Herbrecht R, Thiel E, Haas A, Ruhnke M, Lode H. Efficacy and safety of voriconazole in the treatment of acute invasive aspergillosis. Clin. Infect. Dis., 34, 563-571 (2002).
11. Purkins L, Wood N, Ghahramani P, Greenhalgh K, Allen MJ, Kleinermans D. Pharmacokinetics and safety of voriconazole following intravenous-to oral-dose escalation regimens. Antimicrob. Agents Chemother., 46, 2546-2553 (2002).
12. Jeu L, Piacenti FJ, Lyakhovetskiy AG, Fung HB. Voriconazole. Clin. Ther., 25, 1321-1381 (2003).
13. Roffey SJ, Cole S, Comby P, Gibson D, Jezequel SG, Nedderman AN, Smith DA, Walker DK, Wood N. The disposition of voriconazole in mouse, rat, rabbit, guinea pig, dog, and human. Drug Metab. Dispos., 31, 731-741 (2003).
14. Matsumoto K, Ikawa K, Abematsu K, Fukunaga N, Nishida K, Fukamizu T, Shimodozono Y, Morikawa N, Takeda Y, Yamada K. Correlation between voriconazole trough plasma concentration and hepatotoxicity in patients with different CYP2C19 genotypes. Int. J. Antimicrob. Agents, 34, 91-94 (2009).
15. Wang G, Lei HP, Li Z, Tan ZR, Guo D, Fan L, Chen Y, Hu DL, Wang D, Zhou HH. The CYP2C19 ultra-rapid metabolizer genotype influences the pharmacokinetics of voriconazole in healthy male volunteers. Eur. J. Clin. Pharmacol., 65, 281-285 (2009).
16. Mikus G, Schöwel V, Drzewinska M, Rengelshausen J, Ding R, Riedel KD, Burhenne J, Weiss J, Thomsen T, Haefeli WE. Potent cytochrome P450 2C19 genotype related interaction between voriconazole and the cytochrome P450 3A4 inhibitor ritonavir. Clin. Pharmacol. Ther., 80, 126-135 (2006).
17. Matsuo S, Imai E, Horio M, Yasuda Y, Tomita K, Nitta K, Yamagata K, Tomino Y, Yokoyama H, Hishida A. Collaborators developing the Japanese equation for estimated GFR, revised equations for estimated GFR from serum creatinine in Japan. Am. J. Kidney Dis., 53, 982-992 (2009).
18. Yamada T, Mino Y, Yagi T, Naito T, Kawakami J. Rapid simultaneous determination of voriconazole and its N-oxide in human plasma using an isocratic high-performance liquid chromatography method and its clinical application. Clin. Biochem., 45, 134-138 (2012).
19. Tanigawara Y, Aoyama N, Kita T, Shirakawa K, Komada F, Kasuga M, Okumura K. CYP2C19 genotype-related efficacy of omeprazole for the treatment of infection caused by Helicobacter pylori. Clin. Pharmacol. Ther., 66, 528-534 (1999).
20. Sugimoto K, Uno T, Yamazaki H, Tateishi T. Limited frequency of the CYP2C19∗17 allele and its minor role in a Japanese population. Br. J. Clin. Pharmacol., 65, 437-439 (2008).
21. Myrianthefs P, Markantonis SL, Evaggelopoulou P, Despotelis S, Evodia E, Panidis D, Baltopoulos G. Monitoring plasma voriconazole levels following intravenous administration in critically ill patients: an observational study. Int. J. Antimicrob. Agents, 35, 468-472 (2010).
22. Martin E, Tozer TN, Sheiner LB, Riegelman S. The clinical pharmacokinetics of phenytoin. J. Pharmacokinet. Biopharm., 5, 579-596 (1977).
23. Eiden C, Cociglio M, Hillaire-Buys D, Eymard-Duvernay S, Ceballos P, Fegueux N, Peyrière H. Pharmacokinetic variability of voriconazole and N-oxide voriconazole measured as therapeutic drug monitoring. Xenobiotica, 40, 701-706 (2010).
24. Furuta T, Shirai N, Kodaira M, Sugimoto M, Nogaki A, Kuriyama S, Iwaizumi M, Yamade M, Terakawa I, Ohashi K, Ishizaki T, Hishida A. Pharmacogenomics-based tailored versus standard therapeutic regimen for eradication of H. pylori. Clin. Pharmacol. Ther., 81, 521-528 (2007).
25. Justenhoven C, Hamann U, Pierl CB, Baisch C, Harth V, Rabstein S, Spickenheuer A, Pesch B, Brüning T, Winter S, Ko YD, Brauch H. CYP2C19∗17 is associated with decreased breast cancer risk. Breast Cancer Res. Treat., 115, 391-396 (2009).
26. Kurzawski M, Gawronska-Szklarz B, Wrzesniewska J, Siuda A, Starzynska T, Drozdzik M. Effect of CYP2C19∗17 gene variant on Helicobacter pylori eradication in peptic ulcer patients. Eur. J. Clin. Pharmacol., 62, 877-880 (2006).
27. Mizutani T. PM frequencies of major CYPs in Asians and Caucasians. Drug Metab. Rev., 35, 99-106 (2003).
28. Scholz I, Oberwittler H, Riedel KD, Burhenne J, Weiss J, Haefeli WE, Mikus G. Pharmacokinetics, metabolism and bioavailability of the triazole antifungal agent voriconazole in relation to CYP2C19 genotype. Br. J. Clin. Pharmacol., 68, 906-915 (2009).
29. Zonios D, Yamazaki H, Murayama N, Natarajan V, Palmore T, Childs R, Skinner J, Bennett JE. Voriconazole metabolism, toxicity, and the effect of cytochrome P450 2C19 genotype. J. Infect. Dis., 209, 1941-1948 (2014).