Targeted screen for human UDP-glucuronosyltransferases inhibitors and the evaluation of potential drug-drug interactions with zafirlukast

Drug Metabolism and Disposition

Volumn 43, Issue 6, 2015, Pages 812-818

  Oda, Shingo ^a   Fujiwara, Ryoichi ^b   Kutsuno, Yuki ^b   Fukami, Tatsuki ^a   Itoh, Tomoo ^b   Yokoi, Tsuyoshi ^a   Nakajima, Miki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICLOFENAC; ETODOLAC; FIRTECAN; FUROSEMIDE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A8; HYMECROMONE; NAPROXEN; RALOXIFENE; ZAFIRLUKAST; BILIRUBIN URIDINE-DIPHOSPHOGLUCURONOSYL TRANSFERASE 1A10; ENZYME INHIBITOR; ISOENZYME; LEUKOTRIENE RECEPTOR BLOCKING AGENT; MOLECULAR LIBRARY; RECOMBINANT PROTEIN; SELECTIVE ESTROGEN RECEPTOR MODULATOR; TOLUENESULFONIC ACID DERIVATIVE; UDP-GLUCURONOSYLTRANSFERASE, UGT1A8;

ADULT; AGED; ARTICLE; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG INTERACTION; ENZYME INHIBITION; ENZYME SPECIFICITY; FEMALE; HUMAN; IC50; INTRINSIC CLEARANCE; LIVER MICROSOME; MALE; MICROSOME; PREDICTION; PRIORITY JOURNAL; SMALL INTESTINE; SMALL INTESTINE MICROSOME; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG DETOXIFICATION; DRUG EFFECTS; DRUG SCREENING; ENZYMOLOGY; GENETICS; INTESTINE MUCOSA; KINETICS; METABOLISM; MOLECULAR LIBRARY;

DRUG EVALUATION, PRECLINICAL; DRUG INTERACTIONS; ENZYME INHIBITORS; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINAL MUCOSA; INTESTINE, SMALL; ISOENZYMES; KINETICS; LEUKOTRIENE ANTAGONISTS; METABOLIC DETOXICATION, PHASE II; MICROSOMES; MICROSOMES, LIVER; RALOXIFENE HYDROCHLORIDE; RECOMBINANT PROTEINS; SELECTIVE ESTROGEN RECEPTOR MODULATORS; SMALL MOLECULE LIBRARIES; SUBSTRATE SPECIFICITY; TOSYL COMPOUNDS;

EID: 84940379687     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.062141     Document Type: Article

References (47)

1. Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, and Ni L, et al.; Pharmaceutical Research and Manufacturers of America Drug Metabolism/Clinical Pharmacology Technical Working Groups (2003) The conduct of in vitro and in vivo drug-drug interaction studies: A PhRMA perspective. J Clin Pharmacol 43:443-469.
2. Cheng Y and Prusoff WH (1973) Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
3. Cornish-Bowden A (1995) Control of enzyme activity, in Fundamentals of Enzyme Kinetics, pp 203-216, Portland Press, London.
4. Court MH (2005) Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases. Methods Enzymol 400:104-116.
5. Court MH, Zhang X, Ding X, Yee KK, Hesse LM, and Finel M (2012) Quantitative distribution of mRNAs encoding the 19 human UDP-glucuronosyltransferase enzymes in 26 adult and 3 fetal tissues. Xenobiotica 42:266-277.
6. Dekhuijzen PN and Koopmans PP (2002) Pharmacokinetic profile of zafirlukast. Clin Pharmacokinet 41:105-114.
7. Diasio RB (1998) Sorivudine and 5-fluorouracil; a clinically significant drug-drug interaction due to inhibition of dihydropyrimidine dehydrogenase. Br J Clin Pharmacol 46:1-4.
8. Dresser GK, Spence JD, and Bailey DG (2000) Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin Pharmacokinet 38:41-57.
9. Emoto C, Murase S, Sawada Y, Jones BC, and Iwasaki K (2003) In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: A comparison with SKF-525A and ketoconazole. Drug Metab Pharmacokinet 18:287-295.
10. Emoto C, Murayama N, Rostami-Hodjegan A, and Yamazaki H (2010) Methodologies for investigating drug metabolism at the early drug discovery stage: prediction of hepatic drug clearance and P450 contribution. Curr Drug Metab 11:678-685.
11. Fujita K, Sugiyama M, Akiyama Y, Ando Y, and Sasaki Y (2011) The small-molecule tyrosine kinase inhibitor nilotinib is a potent noncompetitive inhibitor of the SN-38 glucuronidation by human UGT1A1. Cancer Chemother Pharmacol 67:237-241.
12. Fujiwara R, Nakajima M, Yamanaka H, Nakamura A, Katoh M, Ikushiro S, Sakaki T, and Yokoi T (2007) Effects of coexpression of UGT1A9 on enzymatic activities of human UGT1A isoforms. Drug Metab Dispos 35:747-757.
13. Fujiwara R, Nakajima M, Yamanaka H, and Yokoi T (2009) Key amino acid residues responsible for the differences in substrate specificity of human UDP-glucuronosyltransferase (UGT)1A9 and UGT1A8. Drug Metab Dispos 37:41-46.
14. Hanioka N, Jinno H, Nishimura T, Ando M, Ozawa S, and Sawada J (2001) High-performance liquid chromatographic assay for glucuronidation activity of 7-ethyl-10-hydroxycamptothecin (SN-38), the active metabolite of irinotecan (CPT-11), in human liver microsomes. Biomed Chromatogr 15:328-333.
15. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254.
16. Ito K, Iwatsubo T, Kanamitsu S, Nakajima Y, and Sugiyama Y (1998) Quantitative prediction of in vivo drug clearance and drug interactions from in vitro data on metabolism, together with binding and transport. Annu Rev Pharmacol Toxicol 38:461-499.
17. Izukawa T, Nakajima M, Fujiwara R, Yamanaka H, Fukami T, Takamiya M, Aoki Y, Ikushiro S, Sakaki T, and Yokoi T (2009) Quantitative analysis of UDP-glucuronosyltransferase (UGT) 1A and UGT2B expression levels in human livers. Drug Metab Dispos 37:1759-1768.
18. Karonen T, Laitila J, Niemi M, Neuvonen PJ, and Backman JT (2012) Fluconazole but not the CYP3A4 inhibitor, itraconazole, increases zafirlukast plasma concentrations. Eur J Clin Pharmacol 68:681-688.
19. Kato M (2008) Intestinal first-pass metabolism of CYP3A4 substrates. Drug Metab Pharmacokinet 23:87-94.
20. Kemp DC, Fan PW, and Stevens JC (2002) Characterization of raloxifene glucuronidation in vitro: contribution of intestinal metabolism to presystemic clearance. Drug Metab Dispos 30: 694-700.
21. Kiang TK, Ensom MH, and Chang TK (2005) UDP-glucuronosyltransferases and clinical drugdrug interactions. Pharmacol Ther 106:97-132.
22. Kilford PJ, Stringer R, Sohal B, Houston JB, and Galetin A (2009) Prediction of drug clearance by glucuronidation from in vitro data: use of combined cytochrome P450 and UDPglucuronosyltransferase cofactors in alamethicin-activated human liver microsomes. Drug Metab Dispos 37:82-89.
23. King C, Tang W, Ngui J, Tephly T, and Braun M (2001) Characterization of rat and human UDPglucuronosyltransferases responsible for the in vitro glucuronidation of diclofenac. Toxicol Sci 61:49-53.
24. Komura H and Iwaki M (2011) In vitro and in vivo small intestinal metabolism of CYP3A and UGT substrates in preclinical animals species and humans: species differences. Drug Metab Rev 43:476-498.
25. Kuehl GE, Lampe JW, Potter JD, and Bigler J (2005) Glucuronidation of nonsteroidal antiinflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027-1035.
26. Kutsuno Y, Itoh T, Tukey RH, and Fujiwara R (2014) Glucuronidation of drugs and drug-induced toxicity in humanized UDP-glucuronosyltransferase 1 mice. Drug Metab Dispos 42: 1146-1152.
27. Kutsuno Y, Sumida K, Itoh T, Tukey RH, and Fujiwara R (2013) Glucuronidation of drugs in humanized UDP-glucuronosyltransferase 1 mice: Similarity with glucuronidation in human liver microsomes. Pharmacol Res Perspect 1:e00002.
28. Mackenzie PI, Bock KW, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, and Nebert DW (2005) Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677-685.
29. Mano Y, Usui T, and Kamimura H (2007) Comparison of inhibition potentials of drugs against zidovudine glucuronidation in rat hepatocytes and liver microsomes. Drug Metab Dispos 35: 602-606.
30. Mizuma T (2009) Intestinal glucuronidation metabolism may have a greater impact on oral bioavailability than hepatic glucuronidation metabolism in humans: A study with raloxifene, substrate for UGT1A1, 1A8, 1A9, and 1A10. Int J Pharm 378:140-141.
31. Morris RG, Black AB, Lam E, and Westley IS (2000) Clinical study of lamotrigine and valproic acid in patients with epilepsy: using a drug interaction to advantage? Ther Drug Monit 22: 656-660.
32. Obach RS, Walsky RL, Venkatakrishnan K, Gaman EA, Houston JB, and Tremaine LM (2006) The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J Pharmacol Exp Ther 316:336-348.
33. Ohno S and Nakajin S (2009) Determination of mRNA expression of human UDPglucuronosyltransferases and application for localization in various human tissues by realtime reverse transcriptase-polymerase chain reaction. Drug Metab Dispos 37:32-40.
34. Ritter JK (2000) Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 129:171-193.
35. Ritter JK (2007) Intestinal UGTs as potential modifiers of pharmacokinetics and biological responses to drugs and xenobiotics. Expert Opin Drug Metab Toxicol 3:93-107.
36. Rowland A, Elliot DJ, Williams JA, Mackenzie PI, Dickinson RG, and Miners JO (2006) In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction. Drug Metab Dispos 34:1055-1062.
37. Sahai J, Gallicano K, Pakuts A, and Cameron DW (1994) Effect of fluconazole on zidovudine pharmacokinetics in patients infected with human immunodeficiency virus. J Infect Dis 169: 1103-1107.
38. Savidge RD, Bui KH, Birmingham BK, Morse JL, and Spreen RC (1998) Metabolism and excretion of zafirlukast in dogs, rats, and mice. Drug Metab Dispos 26:1069-1076.
39. Shitara Y, Hirano M, Sato H, and Sugiyama Y (2004) Gemfibrozil and its glucuronide inhibit the organic anion transporting polypeptide 2 (OATP2/OATP1B1:SLC21A6)-mediated hepatic uptake and CYP2C8-mediated metabolism of cerivastatin: Analysis of the mechanism of the clinically relevant drug-drug interaction between cerivastatin and gemfibrozil. J Pharmacol Exp Ther 311:228-236.
40. Stingl JC, Bartels H, Viviani R, Lehmann ML, and Brockmöller J (2014) Relevance of UDPglucuronosyltransferase polymorphisms for drug dosing: A quantitative systematic review. Pharmacol Ther 141:92-116.
41. Suttle AB, Vargo DL, Wilkinson LA, Birmingham BK, and Lasseter K (1997) Effect of zafirlukast on the pharmacokinetics of R- And S-warfarin in healthy men (Abstract). Clin Pharmacol Ther 61:186.
42. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581-616.
43. Uchaipichat V, Mackenzie PI, Guo XH, Gardner-Stephen D, Galetin A, Houston JB, and Miners JO (2004) Human udp-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413-423.
44. Watkins JB and Klaassen CD (1983) Chemically-induced alteration of UDP-glucuronic acid concentration in rat liver. Drug Metab Dispos 11:37-40.
45. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, and Ball SE (2004) Drug-drug interactions for UDP-glucuronosyltransferase substrates: A pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201-1208.
46. Zhang D, Chando TJ, Everett DW, Patten CJ, Dehal SS, and Humphreys WG (2005) In vitro inhibition of UDP glucuronosyltransferases by atazanavir and other HIV protease inhibitors and the relationship of this property to in vivo bilirubin glucuronidation. Drug Metab Dispos 33:1729-1739.
47. Zhang L, Zhang YD, Strong JM, Reynolds KS, and Huang SM (2008) A regulatory viewpoint on transporter-based drug interactions. Xenobiotica 38:709-724.