Effects of ketoconazole on glucuronidation by UDP-glucuronosyltransferase enzymes

Clinical Cancer Research

Volumn 11, Issue 18, 2005, Pages 6699-6704

  Yong, Wei Peng ^a   Ramirez, Jacqueline ^a   Innocenti, Federico ^a   Ratain, Mark J ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; 7 ETHYL 10 HYDROXYCAMPTOTHECIN GLUCURONIDE; COMPLEMENTARY DNA; CYCLOSPORIN A; FLUCONAZOLE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; INDINAVIR; IRINOTECAN; ISOENZYME; KETOCONAZOLE; URIDINE DIPHOSPHATE GLUCURONIC ACID;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG METABOLISM; ENZYME INHIBITION; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIVER MICROSOME; PRIORITY JOURNAL;

CAMPTOTHECIN; DOSE-RESPONSE RELATIONSHIP, DRUG; GLUCURONATES; GLUCURONOSYLTRANSFERASE; HEPATOCYTES; HUMANS; INDINAVIR; ISOENZYMES; KETOCONAZOLE; KINETICS; MICROSOMES, LIVER; SUBSTRATE SPECIFICITY;

EID: 25144450011     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-05-0703     Document Type: Article

References (44)

1. Douillard JY, Cunningham D, Roth AD, et al. Irinotecan combined with fluorouracil compared with fluorouracil alone as first-line treatment for metastatic colorectal cancer: a multicentre randomized trial. Lancet 2000;355:1041-7.
2. Saltz LB, Cox JV, Blanke C, et al. Irinotecan plus fluorouracil and leucovorin for metastatic colorectal cancer. N Engl J Med 2000;343:905-14.
3. Humerickhouse R, Lohrbach K, Li L, Bosron WF, Dolan ME. Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res 2000;60:1189-92.
4. Rivory LP, Bowles MR, Robert J, Pond SM. Conversion of irinotecan (CPT-11) to its active metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38), by human liver carboxylesterase. Biochem Pharmacol 1996;52:1103-11.
5. Haaz MC, Riche C, Rivory LP, Robert J. Biosynthesis of an aminopiperidino metabolite of irinotecan [7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxy-camptothecine] by human hepatic microsomes. Drug Metab Dispos 1998a;26:769-74.
6. Haaz MC, Rivory L, Riche C, Vernillet L, Robert J. Metabolism of irinotecan (CPT-11) by human hepatic microsomes: participation of cytochrome P-450 3A and drug interactions. Cancer Res 1998b;58:468-72.
7. Rivory LP, Robert J. Identification and kinetics of a β-glucuronide metabolite of SN-38 in human plasma after administration of the camptothecin derivative irinotecan. Cancer Chemother Pharmacol 1995;36:176-9.
8. Iyer L, King CD, Whitington PF, et al. Genetic predisposition to the metabolism of irinotecan (CPT-11). Role of uridine diphosphate glucuronosyltransferase isoform 1A1 in the glucuronidation of its active metabolite (SN-38) in human liver microsomes. J Clin Invest 1998;101:847-54.
9. Gagne JF, Montminy V, Belanger P, Journault K, Gaucher G, Guillemette C. Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38). Mol Pharmacol 2000;62:608-17.
10. Ciotti M, Basu N, Brangi M, Owens IS. Glucuronidation of 7-ethyl-10-hydroxycamptothecin (SN-38) by the human UDP-glucuronosyltransferases encoded at the UGT1 locus. Biochem Biophys Res Commun 1999;260:199-202.
11. Innocenti F, Undevia SD, Ramirez J, et al. A phase I trial of pharmacologic modulation of irinotecan with cyclosporine and phenobarbital. Clin Pharmacol Ther 2004;76:490-502.
12. Ando Y, Saka H, Ando M, et al. Polymorphisms of UDP- glucuronosyltransferase gene and irinotecan toxicity: a pharmacogenetic analysis. Cancer Res 2000;60:6921-6.
13. Maurice M, Pichard L, Daujat M, et al. Effects of imidazole derivatives on cytochrome P450 from human hepatocytes in primary culture. FASEB J 1992;6:752-8.
14. Achira M, Suzuki H, Ito K, Sugiyama Y. Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother 2002;46:160-5.
15. Kehrer DF, Mathijssen RH, Verweij J, de Bruijn P, Sparreboom A. Modulation of irinotecan metabolism by ketoconazole. J Clin Oncol 2002;20:3122-9.
16. Sawamura R, Sato H, Kawakami J, Iga T. Inhibitory effect of azole antifungal agents on the glucuronidation of lorazepam using rabbit liver microsomes in vitro. Biol Pharm Bull 2000;23:669-71
17. Sampol E, Lacarelle B, Rajaonarison JF, Catalin J, Durand A. Comparative effects of antifungal agents on zidovudine glucuronidation by human liver microsomes. Br J Clin Pharmacol 1995;40:83-6.
18. Asgari M, Back DJ. Effect of azoles on the glucuronidation of zidovudine by human liver UDP-glucuronosyltransferase. J Infect Dis 1995;172:1634-6.
19. Satoh T, Tomikawa Y, Takanashi K, Itoh S, Itoh S, Yoshizawa I. Studies on the interactions between drugs and estrogen. III. Inhibitory effects of 29 drugs reported to induce gynecomastia on the glucuronidation of estradiol. Biol Pharm Bull 2004;27:1844-9.
20. Purba HS, Maggs JL, Orme ML, Back DJ, Park BK. The metabolism of 17 α-ethinyloestradiol by human liver microsomes: formation of catechol and chemically reactive metabolites. Br J Clin Pharmacol 1987;23:447-53.
21. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1996;72:248-54.
22. Zucker SD, Qin X, Rouster SD, et al. Mechanism of indinavir-induced hyperbilirubinemia. Proc Natl Acad Sci U S A 2001;98:12671-6.
23. De Wit S, Debier M, De Smet M, et al. Effect of fluconazole on indinavir pharmacokinetics in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother 1998;42:223-7.
24. Bauer S, Stormer E, Johne A, et al. Alterations in cyclosporin A pharmacokinetics and metabolism during treatment with St John's wort in renal transplant patients. Br J Clin Pharmacol 2003;55:203-11.
25. Burger D, Boyd M, Duncombe C, et al. Pharmacokinetics and pharmacodynamics of indinavir with or without low-dose ritonavir in HIV-infected Thai patients. J Antimicrob Chemother 2003;51:1231-8.
26. Matern H, Heinemann H, Matern S. Radioassay of UDP- glucuronosyltransferase activities toward endogenous substrates using labeled UDP-glucuronic acid and an organic solvent extraction procedure. Anal Biochem 1994;219:182-8.
27. Antoniou T, Gough K, Yoong D, Arbess G. Severe anemia secondary to a probable drug interaction between zidovudine and valproic acid. Clin Infect Dis 2004;38:38-40.
28. Sahai J, Gallicano K, Pakuts A, Cameron DW. Effect of fluconazole on zidovudine pharmacokinetics in patients infected with human immunodeficiency virus. J Infect Dis 1994;169:1103-7.
29. Lee BL, Tauber MG, Sadler B, Goldstein D, Chambers HF. Atovaquone inhibits the glucuronidation and increases the plasma concentrations of zidovudine. Clin Pharmacol Ther 1996;59:14-21.
30. Armstrong SC, Cozza KL. Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, Part II. Psychosomatics 2003;44:515-20.
31. Miners JO, Mackenzie PI. Drug glucuronidation in humans. Pharmacol Ther 1991;51:347-69.
32. Tukey RH, Strassburg CP. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 2000;40:581-616.
33. Rajaonarison JF, Lacarelle B, De Sousa G, Catalin J, Rahmani R. In vitro glucuronidation of 3′-azido-3′-deoxythymidine by human liver. Role of UDP-glucuronosyltransferase 2 form. Drug Metab Dispos 2002;19: 809-15.
34. Brammer KW, Coakley AJ, Jezequel SG, Tarbit MH. The disposition and metabolism of [14C]fluconazole in humans. Drug Metab Dispos 1991;19:764-7.
35. Freemont JJ, Wang R, King CD. Co-immunoprecipitation of UDP-glucuronosyltransferase (UGT) isoforms and cytochrome P450 3A4. Mol Pharmacol 2005;67:260-2.
36. Taura K, Naito E, Ishii Y, Mori MA, Oguri K, Yamada H. Cytochrome P450 1A1 (CYP1A1) inhibitor α-naphthoflavone interferes with UDP-glucuronosyltransferase (UGT) activity in intact but not in permeabilized hepatic microsomes from 3-methylcholanthrene-treated rats: possible involvement of UGT-P450 interactions. Biol Pharm Bull 2004;27:56-60.
37. Taura KI, Yamada H, Hagino Y, Ishii Y, Mori MA, Oguri K. Interaction between cytochrome P450 and other drug-metabolizing enzymes: evidence for an association of CYP1A1 with microsomal epoxide hydrolase and UDP- glucuronosyltransferase. Biochem Biophys Res Commun 2004;273:1048-52.
38. Ayrton A, Morgan P. Role of transport proteins in drug absorption, distribution and excretion. Xenobiotica 2001;31:469-97.
39. Nozawa T, Minami H, Sugiura S, Tsuji A, Tamai I. Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite SN-38: in vitro evidence and effect of single nucleotide polymorphisms. Drug Metab Dispos 2005;33:434-9.
40. Chester JD, Joel SP, Cheeseman SL, et al. Phase I and pharmacokinetic study of intravenous irinotecan plus oral cyclosporin in patients with fuorouracil-refractory metastatic colon cancer. J Clin Oncol 2003;21:1125-32.
41. Gupta E, Safa AR, Wang X, Ratain MJ. Pharmacokinetic modulation of irinotecan and metabolites by cyclosporin A. Cancer Res 1996;56:1309-14.
42. Innocenti F, Undevia SD, Iyer L, et al. Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol 2004;22:1382-8.
43. Watanabe Y, Nakajima M, Ohashi N, Kume T, Yokoi T. Glucuronidation of etoposide in human liver microsomes is specifically catalyzed by UDP-glucuronosyl-transferase1A1. Drug Metab Dispos 2003;31:589-95.
44. Shepard D, Kobayashi K, Wang C, Ratain MJ. Population pharmacokinetic determination of the modulation of oral etoposide (VP-16) elimination by oral ketoconazole. Proc Am Soc Clin Oncol 1998; Abstract No: 732.