Main contribution of UGT1A1 and CYP2C9 in the metabolism of UR-1102, a novel agent for the treatment of gout

References

• Abhishek A, Roddy E, Doherty M. (2017). Gout – a guide for the general and acute physicians. Clin Med (Lond) 17:54–9.
   PubMed Web of Science ®Google Scholar
• Ahn SO, Ohtomo S, Kiyokawa J, et al. (2016). Stronger uricosuric effects of the novel selective URAT1 inhibitor UR-1102 lowered plasma urate in tufted capuchin monkeys to a greater extent than benzbromarone. J Pharmacol Exp Ther 357:157–66.
   PubMed Web of Science ®Google Scholar
• Azevedo VF, Buiar PG, Giovanella LH, et al. (2014). Allopurinol, benzbromarone, or a combination in treating patients with gout: analysis of a series of outpatients. Int J Rheumatol 2014:1–5.
   Google Scholar
• Barter ZE, Bayliss MK, Beaune PH, et al. (2007). Scaling factors for the extrapolation of in vivo metabolic drug clearance from in vitro data: reaching a consensus on values of human microsomal protein and hepatocellularity per gram of liver. Curr Drug Metab 8:33–45.
   PubMed Web of Science ®Google Scholar
• Bohnert T, Patel A, Templeton I, et al. (2016). Evaluation of a new molecular entity as a victim of metabolic drug–drug interactions—an industry perspective. Drug Metab Dispos 44:1399–423.
   PubMed Web of Science ®Google Scholar
• Byeon JY, Lee CM, Lee YJ, et al. (2019). Influence of CYP2D6 genetic polymorphism on pharmacokinetics of active moiety of tolterodine. Arch Pharm Res 42:182–90.
   PubMed Web of Science ®Google Scholar
• Cerny MA. (2016). Prevalence of non-cytochrome P450-mediated metabolism in Food and Drug Administration-approved oral and intravenous drugs: 2006–2015. Drug Metab Dispos 44:1246–52.
   PubMed Web of Science ®Google Scholar
• Chen A, Zhou X, Cheng Y, et al. (2018). Design and optimization of the cocktail assay for rapid assessment of the activity of UGT enzymes in human and rat liver microsomes. Toxicol Lett 295:379–89.
   PubMed Web of Science ®Google Scholar
• Cho N, Kobayashi K, Yoshida M, et al. (2017). Identification of novel glutathione adducts of benzbromarone in human liver microsomes. Drug Metab Pharmacokinet 32:46–52.
   PubMed Web of Science ®Google Scholar
• Cubitt HE, Houston JB, Galetin A. (2011). Prediction of human drug clearance by multiple metabolic pathways: integration of hepatic and intestinal microsomal and cytosolic data. Drug Metab Dispos 39:864–73.
   PubMed Web of Science ®Google Scholar
• Dan T, Koga H, Onuma E, et al. (1989). The activity of AA-193, a new uricosuric agent, in animals. Adv Exp Med Biol 253A:301–8.
   PubMedGoogle Scholar
• Davies B, Morris T. (1993). Physiological parameters in laboratory animals and humans. Pharm Res 10:1093–5.
   PubMed Web of Science ®Google Scholar
• Davies K, Bukhari MAS. (2018). Recent pharmacological advances in the management of gout. Rheumatology (Oxford) 57:951–8.
   PubMed Web of Science ®Google Scholar
• Di L. (2017). Reaction phenotyping to assess victim drug–drug interaction risks. Expert Opin Drug Discov 12:1105–15.
   PubMed Web of Science ®Google Scholar
• Lee CR, Goldstein JA, Pieper JA. (2002). Cytochrome P450 2C9 polymorphisms: a comprehensive review of the in-vitro and human data. Pharmacogenetics 12:251–63.
   PubMedGoogle Scholar
• Fanelli GM, Jr, Bohn D, Stafford S. (1970). Functional characteristics of renal urate transport in the Cebus monkey. Am J Physiol 218:627–36.
   PubMedGoogle Scholar
• Felser A, Lindinger PW, Schnell D, et al. (2014). Hepatocellular toxicity of benzbromarone: effects on mitochondrial function and structure. Toxicology 324:136–46.
   PubMed Web of Science ®Google Scholar
• Franco V, Perucca E. (2015). CYP2C9 polymorphisms and phenytoin metabolism: implications for adverse effects. Expert Opin Drug Metab Toxicol 11:1269–79.
   PubMed Web of Science ®Google Scholar
• Gill KL, Houston JB, Galetin A. (2012). Characterization of in vitro glucuronidation clearance of a range of drugs in human kidney microsomes: comparison with liver and intestinal glucuronidation and impact of albumin. Drug Metab Dispos 40:825–35.
   PubMed Web of Science ®Google Scholar
• Hahn RZ, Antunes MV, Verza SG, et al. (2018). Pharmacokinetic and pharmacogenetic markers of irinotecan toxicity. Curr Med Chem 26(12):2085–2107.
   Web of Science ®Google Scholar
• Harbourt DE, Fallon JK, Ito S, et al. (2012). Quantification of human uridine-diphosphate glucuronosyl transferase 1A isoforms in liver, intestine, and kidney using nanobore liquid chromatography–tandem mass spectrometry. Anal Chem 84:98–105.
   PubMed Web of Science ®Google Scholar
• He L, Li C, Liu X, et al. (2017). Comparative study on the interaction between 3 CYP2C9 allelic isoforms and benzbromarone by using LC-MS/MS method. J Chromatogr B Analyt Technol Biomed Life Sci 1070:97–103.
   PubMed Web of Science ®Google Scholar
• Hong X, Zheng Y, Qin Z, et al. (2017). In vitro glucuronidation of wushanicaritin by liver microsomes, intestine microsomes and expressed human UDP-glucuronosyltransferase enzymes. Int J Mol Sci 18:1983.
   Web of Science ®Google Scholar
• Ito K, Houston JB. (2005). Prediction of human drug clearance from in vitro and preclinical data using physiologically based and empirical approaches. Pharm Res 22:103–12.
   PubMed Web of Science ®Google Scholar
• Iyer L, Das S, Janisch L, et al. (2002). UGT1A1*28 polymorphism as a determinant of irinotecan disposition and toxicity. Pharmacogenomics J 2:43–7.
   PubMedGoogle Scholar
• Jiang X-L, Samant S, Lesko LJ, Schmidt S. (2015). Clinical pharmacokinetics and pharmacodynamics of clopidogrel. Clin Pharmacokinet 54:147–66.
   PubMed Web of Science ®Google Scholar
• Kaufmann P, Török M, Hänni A, et al. (2005). Mechanisms of benzarone and benzbromarone-induced hepatic toxicity. Hepatology 41:925–35.
   PubMed Web of Science ®Google Scholar
• Kazmi F, Barbara JE, Yerino P, Parkinson A. (2015). A long-standing mystery solved: the formation of 3-hydroxydesloratadine is catalyzed by CYP2C8 but prior glucuronidation of desloratadine by UDP-glucuronosyltransferase 2B10 is an obligatory requirement. Drug Metab Dispos 43:523–33.
   PubMed Web of Science ®Google Scholar
• Khojasteh S C, Prabhu S, Kenny J R, et al. (2011). Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: a re-evaluation of P450 isoform selectivity. Eur J Drug Metab Pharmacokinet 36:1–16.
   Google Scholar
• Kim SH, Kim DH, Byeon JY, et al. (2017). Effects of CYP2C9 genetic polymorphisms on the pharmacokinetics of celecoxib and its carboxylic acid metabolite. Arch Pharm Res 40:382–90.
   PubMed Web of Science ®Google Scholar
• Kusama M, Maeda K, Chiba K, et al. (2009). Prediction of the effects of genetic polymorphism on the pharmacokinetics of CYP2C9 substrates from in vitro data. Pharm Res 26:822–35.
   PubMed Web of Science ®Google Scholar
• Lee HA, Yu KS, Park SI, et al. (2019). URC102, a potent and selective inhibitor of hURAT1, reduced serum uric acid in healthy volunteers. Rheumatology 58(11):1976–1984.
   PubMed Web of Science ®Google Scholar
• Lin M, Liu J, Zhou H, et al. (2017). Effects of UDP-glucuronosyltransferase (UGT) polymorphisms on the pharmacokinetics of febuxostat in healthy Chinese volunteers. Drug Metab Pharmacokinet 32:77–84.
   PubMed Web of Science ®Google Scholar
• Mattioli F, Puntoni M, Marini V, et al. (2015). Determination of deferasirox plasma concentrations: do gender, physical and genetic differences affect chelation efficacy? Eur J Haematol 94:310–7.
   PubMed Web of Science ®Google Scholar
• McDonald MG, Rettie AE. (2007). Sequential metabolism and bioactivation of the hepatotoxin benzbromarone: formation of glutathione adducts from a catechol intermediate. Chem Res Toxicol 20:1833–42.
   PubMed Web of Science ®Google Scholar
• Miners JO, Knights KM, Houston JB, Mackenzie PI. (2006). In vitro–in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises. Biochem Pharmacol 71:1531–9.
   PubMed Web of Science ®Google Scholar
• Miyauchi E, Tachikawa M, Decleves X, et al. (2016). Quantitative atlas of cytochrome P450, UDP-glucuronosyltransferase, and transporter proteins in jejunum of morbidly obese subjects. Mol Pharm 13:2631–40.
   PubMed Web of Science ®Google Scholar
• Nakagawa T, Fowler S, Takanashi K, et al. (2018). In vitro metabolism of alectinib, a novel potent ALK inhibitor, in human: contribution of CYP3A enzymes. Xenobiotica 48:546–54.
   PubMed Web of Science ®Google Scholar
• Oda S, Fukami T, Yokoi T, Nakajima M. (2015). A comprehensive review of UDP-glucuronosyltransferase and esterases for drug development. Drug Metab Pharmacokinet 30:30–51.
   PubMed Web of Science ®Google Scholar
• Proctor NJ, Tucker GT, Rostami-Hodjegan A. (2004). Predicting drug clearance from recombinantly expressed CYPs: intersystem extrapolation factors. Xenobiotica 34:151–78.
   PubMed Web of Science ®Google Scholar
• Reinders MK, van Roon EN, Houtman PM, et al. (2007). Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients. Clin Rheumatol 26:1459–65.
   PubMed Web of Science ®Google Scholar
• Roch-Ramel F, Peters G. 1978. Urinary excretion of uric acid in nonhuman mammalian species. In: Kelley WN, Weiner IM, editors. Uric acid. Berlin, Heidelberg, New York: Springer, 211–55.
   Google Scholar
• Rouguieg K, Picard N, Sauvage FL, et al. (2010). Contribution of the different UDP-glucuronosyltransferase (UGT) isoforms to buprenorphine and norbuprenorphine metabolism and relationship with the main UGT polymorphisms in a bank of human liver microsomes. Drug Metab Dispos 38:40–5.
   PubMed Web of Science ®Google Scholar
• Shahid H, Singh JA. (2015). Investigational drugs for hyperuricemia. Expert Opin Investig Drugs 24:1013–30.
   PubMed Web of Science ®Google Scholar
• Shaul C, Blotnick S, Muszkat M, et al. (2017). Quantitative assessment of CYP2C9 genetic polymorphisms effect on the oral clearance of S-warfarin in healthy subjects. Mol Diagn Ther 21:75–83.
   PubMed Web of Science ®Google Scholar
• Shirasu H, Todaka A, Omae K, et al. (2019). Impact of UGT1A1 genetic polymorphism on toxicity in unresectable pancreatic cancer patients undergoing FOLFIRINOX. Cancer Sci 110:707–16.
   PubMed Web of Science ®Google Scholar
• Soars MG, Burchell B, Riley RJ. (2002). In vitro analysis of human drug glucuronidation and prediction of in vivo metabolic clearance. J Pharmacol Exp Ther 301:382–90.
   PubMed Web of Science ®Google Scholar
• Stingl JC, Bartels H, Viviani R, et al. (2014). Relevance of UDP-glucuronosyltransferase polymorphisms for drug dosing: a quantitative systematic review. Pharmacol Ther 141:92–116.
   PubMed Web of Science ®Google Scholar
• Sun H, Wang H, Liu H, et al. (2014). Glucuronidation of capsaicin by liver microsomes and expressed UGT enzymes: reaction kinetics, contribution of individual enzymes and marked species differences. Expert Opin Drug Metab Toxicol 10:1325–36.
   PubMed Web of Science ®Google Scholar
• Xiao L, Zhu L, Li W, et al. (2018). New insights into SN-38 glucuronidation: evidence for the important role of UDP glucuronosyltransferase 1A9. Basic Clin Pharmacol Toxicol 122:424–8.
   PubMed Web of Science ®Google Scholar
• Yamane M, Kawashima K, Yamaguchi K, et al. (2015). In vitro profiling of the metabolism and drug–drug interaction of tofogliflozin, a potent and highly specific sodium-glucose co-transporter 2 inhibitor, using human liver microsomes, human hepatocytes, and recombinant human CYP. Xenobiotica 45:230–8.
   PubMed Web of Science ®Google Scholar
• Yamasaki C, Kataoka M, Kato Y, et al. (2010). In vitro evaluation of cytochrome P450 and glucuronidation activities in hepatocytes isolated from liver-humanized mice. Drug Metab Pharmacokinet 25:539–50.
   PubMed Web of Science ®Google Scholar
• Yasar Ü, Eliasson E, Forslund-Bergengren C, et al. (2001). The role of CYP2C9 genotype in the metabolism of diclofenac in vivo and in vitro. Eur J Clin Pharmacol 57:729–35.
   PubMed Web of Science ®Google Scholar
• Yong M, Schwartz SM, Atkinson C, et al. (2011). Associations between polymorphisms in glucuronidation and sulfation enzymes and sex steroid concentrations in premenopausal women in the United States. J Steroid Biochem Mol Biol 124:10–8.
   PubMed Web of Science ®Google Scholar
• Zhang D, Chando TJ, Everett DW, et al. (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 33:1729–39.
   PubMed Web of Science ®Google Scholar
• Zhang D, Zhang D, Cui D, et al. (2007). Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. Drug Metab Dispos 35:2270–80.
   PubMed Web of Science ®Google Scholar
• Zhang MY, Niu JQ, Wen XY, et al. (2019). Liver failure associated with benzbromarone: a case report and review of the literature. World J Clin Cases 7:1717–25.
   PubMed Web of Science ®Google Scholar
• Zientek MA, Youdim K. (2015). Reaction phenotyping: advances in the experimental strategies used to characterize the contribution of drug-metabolizing enzymes. Drug Metab Dispos 43:163–81.
   PubMed Web of Science ®Google Scholar