N-glucuronidation of drugs and other xenobiotics by human and animal UDP-glucuronosyltransferases

References

• Alonen A, Finel M, Kostiainen R. (2008). The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan. Biochem Pharmacol 76:763–772.
   PubMed Web of Science ®Google Scholar
• Bailey MJ, Dickinson RG. (2003). Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 145:117–137.
   PubMed Web of Science ®Google Scholar
• Berg JZ, Mason J, Boettcher AJ, Hatsukami DK, Murphy SE. (2010a). Nicotine metabolism in African Americans and European Americans: variation in glucuronidation by ethnicity and UGT2B10 haplotype. J Pharmacol Exp Ther 332:202–209.
   PubMed Web of Science ®Google Scholar
• Berg JZ, von Weymarn LB, Thompson EA, Wickham KM, Weisensel NA, Hatsukami DK, Murphy SE. (2010b). UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption. Cancer Epidemiol Biomarkers Prev 19:1423–1431.
   PubMed Web of Science ®Google Scholar
• Borlak J, Gasparic A, Locher M, Schupke H, Hermann R. (2006). N-glucuronidation of the antiepileptic drug retigabine: results from studies with human volunteers, heterologously expressed human UGTs, human liver, kidney, and liver microsomal membranes of Crigler-Najjar type II. Metab Clin Exp 55:711–721.
   PubMedGoogle Scholar
• Breyer-Pfaff U, Fischer D, Winne D. (1997). Biphasic kinetics of quaternary ammonium glucuronide formation from amitriptyline and diphenhydramine in human liver microsomes. Drug Metab Dispos 25:340–345.
   PubMed Web of Science ®Google Scholar
• Breyer-Pfaff U, Mey U, Green MD, Tephly TR. (2000). Comparative N-glucuronidation kinetics of ketotifen and amitriptyline by expressed human UDP-glucuronosyltransferases and liver microsomes. Drug Metab Dispos 28:869–872.
   PubMed Web of Science ®Google Scholar
• Bruck M, Li Q, Lamb JG, Tukey RH. (1997). Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4. Arch Biochem Biophys 348:357–364.
   Google Scholar
• Burchell B, Coughtrie MW. (1989). UDP-glucuronosyltransferases. Pharmacol Ther 43:261–289.
   PubMed Web of Science ®Google Scholar
• Burchell B, Lockley DJ, Staines A, Uesawa Y, Coughtrie MW. (2005). Substrate specificity of human hepatic UDP-glucuronosyltransferases. Meth Enzymol 400:46–57.
   PubMed Web of Science ®Google Scholar
• Chen G, Blevins-Primeau AS, Dellinger RW, Muscat JE, Lazarus P. (2007). Glucuronidation of nicotine and cotinine by UGT2B10: loss of function by the UGT2B10 Codon 67 (Asp>Tyr) polymorphism. Cancer Res 67:9024–9029.
   PubMed Web of Science ®Google Scholar
• Chen G, Dellinger RW, Gallagher CJ, Sun D, Lazarus P. (2008a). Identification of a prevalent functional missense polymorphism in the UGT2B10 gene and its association with UGT2B10 inactivation against tobacco-specific nitrosamines. Pharmacogenet Genomics 18:181–191.
   PubMed Web of Science ®Google Scholar
• Chen G, Dellinger RW, Sun D, Spratt TE, Lazarus P. (2008b). Glucuronidation of tobacco-specific nitrosamines by UGT2B10. Drug Metab Dispos 36:824–830.
   PubMed Web of Science ®Google Scholar
• Chiu SH, Huskey SW. (1998). Species differences in N-glucuronidation. Drug Metab Dispos 26:838–847.
   PubMed Web of Science ®Google Scholar
• Ciotti M, Lakshmi VM, Basu N, Davis BB, Owens IS, Zenser TV. (1999). Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucuronides. Carcinogenesis 20:1963–1969.
   PubMed Web of Science ®Google Scholar
• Clarke DJ, Burchell B. (1994). The uridine diphosphate glucuronosyltransferase multigene family: function and regulation. In: Kaufman FC, ed. Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity. New York, Springer-Verlag: pp 3–43.
   Google Scholar
• Coughtrie MW. (2002). Sulfation through the looking glass–recent advances in sulfotransferase research for the curious. Pharmacogenomics J 2:297–308.
   PubMedGoogle Scholar
• Coughtrie MW, Sharp S. (1991). Glucuronidation of imipramine in rabbit and human liver microsomes: assay conditions and interaction with other tertiary amine drugs. Biochem Pharmacol 42:1497–1501.
   PubMed Web of Science ®Google Scholar
• Court MH. (2010). Interindividual variability in hepatic drug glucuronidation: studies into the role of age, sex, enzyme inducers, and genetic polymorphism using the human liver bank as a model system. Drug Metab Rev 42:209–224.
   PubMed Web of Science ®Google Scholar
• Court MH. (2005). Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases. Meth Enzymol 400:104–116.
   PubMed Web of Science ®Google Scholar
• Court MH, Greenblatt DJ. (2000). Molecular genetic basis for deficient acetaminophen glucuronidation by cats: UGT1A6 is a pseudogene, and evidence for reduced diversity of expressed hepatic UGT1A isoforms. Pharmacogenetics 10:355–369.
   PubMedGoogle Scholar
• Court MH, Hazarika S, Krishnaswamy S, Finel M, Williams JA. (2008). Novel polymorphic human UDP-glucuronosyltransferase 2A3: cloning, functional characterization of enzyme variants, comparative tissue expression, and gene induction. Mol Pharmacol 74:744–754.
   PubMed Web of Science ®Google Scholar
• Dahl-Puustinen ML, Aberg-Wistedt A, Bertilsson L. (1989). Glucuronidation of amitriptyline in man in vivo. Pharmacol Toxicol 65:37–39.
   PubMedGoogle Scholar
• Dellinger RW, Chen G, Blevins-Primeau AS, Krzeminski J, Amin S, Lazarus P. (2007). Glucuronidation of PhIP and N-OH-PhIP by UDP-glucuronosyltransferase 1A10. Carcinogenesis 28:2412–2418.
   PubMed Web of Science ®Google Scholar
• Ebner T, Burchell B. (1993). Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family. Drug Metab Dispos 21:50–55.
   PubMed Web of Science ®Google Scholar
• Finel M, Li X, Gardner-Stephen D, Bratton S, Mackenzie PI, Radominska-Pandya A. (2005). Human UDP-glucuronosyltransferase 1A5: identification, expression, and activity. J Pharmacol Exp Ther 315:1143–1149.
   PubMed Web of Science ®Google Scholar
• Gamage N, Barnett A, Hempel N, Duggleby RG, Windmill KF, Martin JL, McManus ME. (2006). Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5–22.
   PubMed Web of Science ®Google Scholar
• Ghosheh O, Hawes EM. (2002). Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation. Drug Metab Dispos 30:1478–1483.
   PubMed Web of Science ®Google Scholar
• Girard H, Thibaudeau J, Court MH, Fortier LC, Villeneuve L, Caron P, Hao Q, von Moltke LL, Greenblatt DJ, Guillemette C. (2005). UGT1A1 polymorphisms are important determinants of dietary carcinogen detoxification in the liver. Hepatology 42:448–457.
   PubMed Web of Science ®Google Scholar
• Green MD, Bishop WP, Tephly TR. (1995). Expressed human UGT1.4 protein catalyzes the formation of quaternary ammonium-linked glucuronides. Drug Metab Dispos 23:299–302.
   PubMed Web of Science ®Google Scholar
• Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR. (1998). Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26:507–512.
   PubMed Web of Science ®Google Scholar
• Green MD, Tephly TR. (1996). Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug Metab Dispos 24:356–363.
   PubMed Web of Science ®Google Scholar
• Green MD, Tephly TR. (1998). Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins. Drug Metab Dispos 26:860–867.
   PubMed Web of Science ®Google Scholar
• Guengerich FP. (2008). Oxidative, reductive and hydrolytic metabolism of drugs. In: Zhang D, Zhu M, Humphreys WG, eds. Drug Metabolism in Drug Design and Development. Hoboken, New Jersey, Wiley Interscience: pp 15–36.
   Google Scholar
• Hawes EM. (1998). N+-glucuronidation, a common pathway in human metabolism of drugs with a tertiary amine group. Drug Metab Dispos 26:830–837.
   PubMed Web of Science ®Google Scholar
• Hempel R, Schupke H, McNeilly PJ, Heinecke K, Kronbach C, Grunwald C, Zimmermann G, Griesinger C, Engel J, Kronbach T. (1999). Metabolism of retigabine (D-23129), a novel anticonvulsant. Drug Metab Dispos 27:613–622.
   PubMed Web of Science ®Google Scholar
• Hukkanen J, Jacob P 3rd, Benowitz NL. (2005). Metabolism and disposition kinetics of nicotine. Pharmacol Rev 57:79–115.
   PubMed Web of Science ®Google Scholar
• Ikushiro S, Emi Y, Iyanagi T. (1995). Identification and analysis of drug-responsive expression of UDP-glucuronosyltransferase family 1 (UGT1) isozyme in rat hepatic microsomes using anti-peptide antibodies. Arch Biochem Biophys 324:267–272.
   PubMed Web of Science ®Google Scholar
• Itäaho K, Mackenzie PI, Ikushiro S, Miners JO, Finel M. (2008). The configuration of the 17-hydroxy group variably influences the glucuronidation of beta-estradiol and epiestradiol by human UDP-glucuronosyltransferases. Drug Metab Dispos 36:2307–2315.
   PubMed Web of Science ®Google Scholar
• Izukawa T, Nakajima M, Fujiwara R, Yamanaka H, Fukami T, Takamiya M, Aoki Y, Ikushiro S, Sakaki T, Yokoi T. (2009). Quantitative analysis of UDP-glucuronosyltransferase (UGT) 1A and UGT2B expression levels in human livers. Drug Metab Dispos 37:1759–1768.
   PubMed Web of Science ®Google Scholar
• Jedlitschky G, Cassidy AJ, Sales M, Pratt N, Burchell B. (1999). Cloning and characterization of a novel human olfactory UDP-glucuronosyltransferase. Biochem J 340 (Pt 3):837–843.
   PubMedGoogle Scholar
• Kaderlik KR, Mulder GJ, Turesky RJ, Lang NP, Teitel CH, Chiarelli MP, Kadlubar FF. (1994). Glucuronidation of N-hydroxy heterocyclic amines by human and rat liver microsomes. Carcinogenesis 15:1695–1701.
   Google Scholar
• Kaivosaari S, Toivonen P, Aitio O, Sipilä J, Koskinen M, Salonen JS, Finel M. (2008). Regio- and stereospecific N-glucuronidation of medetomidine: the differences between UDP glucuronosyltransferase (UGT) 1A4 and UGT2B10 account for the complex kinetics of human liver microsomes. Drug Metab Dispos 36:1529–1537.
   PubMed Web of Science ®Google Scholar
• Kaivosaari S, Toivonen P, Hesse LM, Koskinen M, Court MH, Finel M. (2007). Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10. Mol Pharmacol 72:761–768.
   PubMed Web of Science ®Google Scholar
• Kaji H, Kume T. (2005). Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). Drug Metab Dispos 33:60–67.
   PubMed Web of Science ®Google Scholar
• Kaku T, Ogura K, Nishiyama T, Ohnuma T, Muro K, Hiratsuka A. (2004). Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochem Pharmacol 67:2093–2102.
   PubMed Web of Science ®Google Scholar
• Kassahun K, Mattiuz E, Franklin R, Gillespie T. (1998). Olanzapine 10-N-glucuronide. A tertiary N-glucuronide unique to humans. Drug Metab Dispos 26:848–855.
   PubMed Web of Science ®Google Scholar
• Kerdpin O, Mackenzie PI, Bowalgaha K, Finel M, Miners JO. (2009). Influence of N-terminal domain histidine and proline residues on the substrate selectivities of human UDP-glucuronosyltransferase 1A1, 1A6, 1A9, 2B7, and 2B10. Drug Metab Dispos 37:1948–1955.
   PubMed Web of Science ®Google Scholar
• Kilford PJ, Stringer R, Sohal B, Houston JB, Galetin A. (2009). Prediction of drug clearance by glucuronidation from in vitro data: use of combined cytochrome P450 and UDP-glucuronosyltransferase cofactors in alamethicin-activated human liver microsomes. Drug Metab Dispos 37:82–89.
   PubMed Web of Science ®Google Scholar
• King CD, Green MD, Rios GR, Coffman BL, Owens IS, Bishop WP, Tephly TR. (1996). The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1. Arch Biochem Biophys 332:92–100.
   PubMed Web of Science ®Google Scholar
• King CD, Rios GR, Green MD, Tephly TR. (2000). UDP-glucuronosyltransferases. Curr Drug Metab 1:143–161.
   PubMed Web of Science ®Google Scholar
• Klieber S, Hugla S, Ngo R, Arabeyre-Fabre C, Meunier V, Sadoun F, Fedeli O, Rival M, Bourrie M, Guillou F, Maurel P, Fabre G. (2008). Contribution of the N-glucuronidation pathway to the overall in vitro metabolic clearance of midazolam in humans. Drug Metab Dispos 36:851–862.
   PubMed Web of Science ®Google Scholar
• Kuehl GE, Lampe JW, Potter JD, Bigler J. (2005). Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027–1035.
   PubMed Web of Science ®Google Scholar
• Lautala P, Ethell BT, Taskinen J, Burchell B. (2000). The specificity of glucuronidation of entacapone and tolcapone by recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos 28:1385–1389.
   PubMed Web of Science ®Google Scholar
• Lautala P, Kivimaa M, Salomies H, Elovaara E, Taskinen J. (1997). Glucuronidation of entacapone, nitecapone, tolcapone, and some other nitrocatechols by rat liver microsomes. Pharm Res 14:1444–1448.
   PubMed Web of Science ®Google Scholar
• Lin J, Sahakian DC, de Morais SM, Xu JJ, Polzer RJ, Winter SM. (2003). The role of absorption, distribution, metabolism, excretion and toxicity in drug discovery. Curr Top Med Chem 3:1125–1154.
   PubMed Web of Science ®Google Scholar
• Luo H, Hawes EM, McKay G, Korchinski ED, Midha KK. (1991). N(+)-glucuronidation of aliphatic tertiary amines, a general phenomenon in the metabolism of H1-antihistamines in humans. Xenobiotica 21:1281–1288.
   PubMed Web of Science ®Google Scholar
• Luo H, Hawes EM, McKay G, Korchinski ED, Midha KK. (1995). N(+)-glucuronidation of aliphatic tertiary amines in human: antidepressant versus antipsychotic drugs. Xenobiotica 25:291–301.
   PubMed Web of Science ®Google Scholar
• Luukkanen L, Taskinen J, Kurkela M, Kostiainen R, Hirvonen J, Finel M. (2005). Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos 33:1017–1026.
   PubMed Web of Science ®Google Scholar
• Mackenzie PI, Bock KW, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, Nebert DW. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–685.
   PubMed Web of Science ®Google Scholar
• Mackenzie PI, Gregory PA, Gardner-Stephen DA, Lewinsky RH, Jorgensen BR, Nishiyama T, Xie W, Radominska-Pandya A. (2003). Regulation of UDP glucuronosyltransferase genes. Curr Drug Metab 4:249–257.
   PubMed Web of Science ®Google Scholar
• Magdalou J, Herber R, Bidault R, Siest G. (1992). In vitro N-glucuronidation of a novel antiepileptic drug, lamotrigine, by human liver microsomes. J Pharmacol Exp Ther 260:1166–1173.
   PubMed Web of Science ®Google Scholar
• Mey U, Wachsmuth H, Breyer-Pfaff U. (1999). Conjugation of the enantiomers of ketotifen to four isomeric quaternary ammonium glucuronides in humans in vivo and in liver microsomes. Drug Metab Dispos 27:1281–1292.
   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 71:1531–1539.
   PubMed Web of Science ®Google Scholar
• Miners JO, Mackenzie PI. (1991). Drug glucuronidation in humans. Pharmacol Ther 51:347–369.
   PubMed Web of Science ®Google Scholar
• Nakajima M, Tanaka E, Kobayashi T, Ohashi N, Kume T, Yokoi T. (2002). Imipramine N-glucuronidation in human liver microsomes: biphasic kinetics and characterization of UDP-glucuronosyltransferase isoforms. Drug Metab Dispos 30:636–642.
   PubMed Web of Science ®Google Scholar
• Nakazawa T, Miyata K, Omura K, Iwanaga T, Nagata O. (2006). Metabolic profile of FYX-051 (4-(5-pyridin-4-yl-1h-[1,2,4]triazol-3-yl)pyridine-2-carbonitrile) in the rat, dog, monkey, and human: identification of N-glucuronides and N-glucosides. Drug Metab Dispos 34:1880–1886.
   Google Scholar
• Nishimura M, Naito S. (2006). Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes. Drug Metab Pharmacokinet 21:357–374.
   PubMed Web of Science ®Google Scholar
• Ohno S, Nakajin S. (2009). Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction. Drug Metab Dispos 37:32–40.
   PubMed Web of Science ®Google Scholar
• Omura K, Nakazawa T, Sato T, Iwanaga T, Nagata O. (2007). Characterization of N-glucuronidation of 4-(5-pyridin-4-yl-1H-[1,2,4]triazol-3-yl) pyridine-2-carbonitrile (FYX-051): a new xanthine oxidoreductase inhibitor. Drug Metab Dispos 35:2143–2148.
   Google Scholar
• Ouzzine M, Barré L, Netter P, Magdalou J, Fournel-Gigleux S. (2003). The human UDP-glucuronosyltransferases: structural aspects and drug glucuronidation. Drug Metab Rev 35:287–303.
   PubMed Web of Science ®Google Scholar
• Pelkonen O. (2002). Human CYPs: in vivo and clinical aspects. Drug Metab Rev 34:37–46.
   PubMed Web of Science ®Google Scholar
• Pelkonen O, Kapitulnik J, Gundert-Remy U, Boobis AR, Stockis A. (2008). Local kinetics and dynamics of xenobiotics. Crit Rev Toxicol 38:697–720.
   PubMed Web of Science ®Google Scholar
• Remmel RP, Nagar S, Argikar U. (2008). Conjugative metabolism of drugs. In: Zhang D, Zhu M and Humphreys WG eds. Drug Metabolism in Drug Design and Development. Hoboken, New Jersey, Wiley Interscience: pp 37–62.
   Google Scholar
• Rowland A, Elliot DJ, Williams JA, Mackenzie PI, Dickinson RG, Miners JO. (2006). In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction. Drug Metab Dispos 34:1055–1062.
   PubMed Web of Science ®Google Scholar
• Rush WR, Alexander OF, Hall DJ, Dow RJ, Tokes L, Kurz L, Graham DJ. (1990). The metabolism of nafimidone hydrochloride in the dog, primates and man. Xenobiotica 20:123–132.
   PubMed Web of Science ®Google Scholar
• Sallustio BC, Sabordo L, Evans AM, Nation RL. (2000). Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab 1:163–180.
   PubMed Web of Science ®Google Scholar
• Senafi SB, Clarke DJ, Burchell B. (1994). Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem J 303 (Pt 1):233–240.
   Google Scholar
• Shiratani H, Katoh M, Nakajima M, Yokoi T. (2008). Species differences in UDP-glucuronosyltransferase activities in mice and rats. Drug Metab Dispos 36:1745–1752.
   PubMed Web of Science ®Google Scholar
• Singh SS. (2006). Preclinical pharmacokinetics: an approach towards safer and efficacious drugs. Curr Drug Metab 7:165–182.
   PubMed Web of Science ®Google Scholar
• Sinz MW, Remmel RP. (1991). Isolation and characterization of a novel quaternary ammonium-linked glucuronide of lamotrigine. Drug Metab Dispos 19:149–153.
   PubMed Web of Science ®Google Scholar
• Sneitz N, Court MH, Zhang X, Laajanen K, Yee KK, Dalton P, Ding X, Finel M. (2009). Human UDP-glucuronosyltransferase UGT2A2: cDNA construction, expression, and functional characterization in comparison with UGT2A1 and UGT2A3. Pharmacogenet Genomics 19:923–934.
   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 301:382–390.
   PubMed Web of Science ®Google Scholar
• Soars MG, Fettes M, O’Sullivan AC, Riley RJ, Ethell BT, Burchell B. (2003). Cloning and characterisation of the first drug-metabolising canine UDP-glucuronosyltransferase of the 2B subfamily. Biochem Pharmacol 65:1251–1259.
   Google Scholar
• Soars MG, Riley RJ, Burchell B. (2001a). Evaluation of the marmoset as a model species for drug glucuronidation. Xenobiotica 31:849–860.
   PubMed Web of Science ®Google Scholar
• Soars MG, Riley RJ, Findlay KA, Coffey MJ, Burchell B. (2001b). Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug Metab Dispos 29:121–126.
   PubMed Web of Science ®Google Scholar
• Staines AG, Coughtrie MW, Burchell B. (2004). N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther 311:1131–1137.
   PubMed Web of Science ®Google Scholar
• Sten T, Bichlmaier I, Kuuranne T, Leinonen A, Yli-Kauhaluoma J, Finel M. (2009). UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. Drug Metab Dispos 37:417–423.
   PubMed Web of Science ®Google Scholar
• Stevens JC, Fayer JL, Cassidy KC. (2001). Characterization of 2-[[4-[[2-(1H-tetrazol-5-ylmethyl)phenyl]methoxy]methyl]quinoline N-glucuronidation by in vitro and in vivo approaches. Drug Metab Dispos 29:289–295.
   PubMed Web of Science ®Google Scholar
• Stone AN, Mackenzie PI, Galetin A, Houston JB, Miners JO. (2003). Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human UDP-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 31:1086–1089.
   PubMed Web of Science ®Google Scholar
• Tsai MC, Gorrod JW. (1999). Evidence for the biosynthesis of A glucuronide conjugate of (S)-(-)-nicotine, but not (S)-(-)-cotinine or (+/-)-trans-3′-hydroxycotinine by marmoset hepatic microsomes. Drug Metabol Drug Interact 15:223–237.
   PubMedGoogle Scholar
• Tukey RH, Strassburg CP. (2000). Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581–616.
   PubMed Web of Science ®Google Scholar
• Turgeon D, Carrier JS, Lévesque E, Hum DW, Bélanger A. (2001). Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members. Endocrinology 142:778–787.
   PubMed Web of Science ®Google Scholar
• Uchaipichat V, Mackenzie PI, Elliot DJ, Miners JO. (2006). Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) “probes” for human UDP-glucuronosyltransferases. Drug Metab Dispos 34:449–456.
   PubMed Web of Science ®Google Scholar
• Uesawa Y, Staines AG, Lockley D, Mohri K, Burchell B. (2007). Identification of the human liver UDP-glucuronosyltransferase involved in the metabolism of p-ethoxyphenylurea (dulcin). Arch Toxicol 81:163–168.
   Google Scholar
• Uesawa Y, Staines AG, O’Sullivan A, Mohri K, Burchell B. (2004). Identification of the rabbit liver UDP-glucuronosyltransferase catalyzing the glucuronidation of 4-ethoxyphenylurea (dulcin). Drug Metab Dispos 32:1476–1481.
   Google Scholar
• Vashishtha SC, Hawes EM, McCann DJ, Ghosheh O, Hogg L. (2002). Quaternary ammonium-linked glucuronidation of 1-substituted imidazoles by liver microsomes: interspecies differences and structure-metabolism relationships. Drug Metab Dispos 30:1070–1076.
   PubMed Web of Science ®Google Scholar
• Wells PG, Mackenzie PI, Chowdhury JR, Guillemette C, Gregory PA, Ishii Y, Hansen AJ, Kessler FK, Kim PM, Chowdhury NR, Ritter JK. (2004). Glucuronidation and the UDP-glucuronosyltransferases in health and disease. Drug Metab Dispos 32:281–290.
   PubMed Web of Science ®Google Scholar
• Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, 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.
   PubMed Web of Science ®Google Scholar
• Xu L, Krenitsky DM, Seacat AM, Butenhoff JL, Tephly TR, Anders MW. (2006). N-glucuronidation of perfluorooctanesulfonamide by human, rat, dog, and monkey liver microsomes and by expressed rat and human UDP-glucuronosyltransferases. Drug Metab Dispos 34:1406–1410.
   Google Scholar
• Yan Z, Caldwell GW, Gauthier D, Leo GC, Mei J, Ho CY, Jones WJ, Masucci JA, Tuman RW, Galemmo RA Jr, Johnson DL. (2006). N-glucuronidation of the platelet-derived growth factor receptor tyrosine kinase inhibitor 6,7-(dimethoxy-2,4-dihydroindeno[1,2-C]pyrazol-3-yl)-(3-fluoro-phenyl)-amine by human UDP-glucuronosyltransferases. Drug Metab Dispos 34:748–755.
   PubMed Web of Science ®Google Scholar
• Yin H, Bennett G, Jones JP. (1994). Mechanistic studies of uridine diphosphate glucuronosyltransferase. Chem Biol Interact 90:47–58.
   PubMed Web of Science ®Google Scholar
• Zamek-Gliszczynski MJ, Hoffmaster KA, Nezasa K, Tallman MN, Brouwer KL. (2006). Integration of hepatic drug transporters and phase II metabolizing enzymes: mechanisms of hepatic excretion of sulfate, glucuronide, and glutathione metabolites. Eur J Pharm Sci 27:447–486.
   PubMed Web of Science ®Google Scholar
• Zenser TV, Lakshmi VM, Davis BB. (1998). N-glucuronidation of benzidine and its metabolites. Role in bladder cancer. Drug Metab Dispos 26:856–859.
   PubMed Web of Science ®Google Scholar
• Zenser TV, Lakshmi VM, Hsu FF, Davis BB. (2002). Metabolism of N-acetylbenzidine and initiation of bladder cancer. Mutat Res 506-507:29–40.
   PubMed Web of Science ®Google Scholar
• Zhang D, Zhao W, Roongta VA, Mitroka JG, Klunk LJ, Zhu M. (2004). Amide N-glucuronidation of MaxiPost catalyzed by UDP-glucuronosyltransferase 2B7 in humans. Drug Metab Dispos 32:545–551.
   PubMedGoogle Scholar
• Zhou D, Guo J, Linnenbach AJ, Booth-Genthe CL, Grimm SW. (2010). Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine. Drug Metab Dispos 38:863–870.
   PubMed Web of Science ®Google Scholar