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Volumn 76, Issue 6, 2008, Pages 763-772

The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan

Author keywords

Candesartan; Losartan; Substrate specificity; Tetrazole; UDP glucuronosyltransferases; Zolarsartan (GR117289)

Indexed keywords

ANGIOTENSIN 1 RECEPTOR ANTAGONIST; CANDESARTAN; GLUCURONOSYLTRANSFERASE 1A3; LOSARTAN; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZOLARSARTAN; ZOLASARTAN;

EID: 50549104173     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.07.006     Document Type: Article
Times cited : (58)

References (40)
  • 1
    • 33645672459 scopus 로고    scopus 로고
    • Losartan, an AT1 antagonist, prevents aortic aneurysm in a mouse model of Marfan syndrome
    • Habashi J.P., Judge D.P., Holm T.M., Cohn R.D., Loeys B.L., Cooper T.K., et al. Losartan, an AT1 antagonist, prevents aortic aneurysm in a mouse model of Marfan syndrome. Science 312 (2006) 117-121
    • (2006) Science , vol.312 , pp. 117-121
    • Habashi, J.P.1    Judge, D.P.2    Holm, T.M.3    Cohn, R.D.4    Loeys, B.L.5    Cooper, T.K.6
  • 2
    • 38649094252 scopus 로고    scopus 로고
    • Recent advances in understanding Marfan syndrome: should we now treat surgical patients with losartan?
    • Matt P., Habashi J., Carrel T., Cameron D.E., Van Eyk J.E., and Dietz H.C. Recent advances in understanding Marfan syndrome: should we now treat surgical patients with losartan?. J Thorac Cardiovasc Surg 135 (2008) 389-394
    • (2008) J Thorac Cardiovasc Surg , vol.135 , pp. 389-394
    • Matt, P.1    Habashi, J.2    Carrel, T.3    Cameron, D.E.4    Van Eyk, J.E.5    Dietz, H.C.6
  • 3
    • 33645739610 scopus 로고    scopus 로고
    • Medicine. Old drug, new hope for Marfan syndrome
    • Travis J. Medicine. Old drug, new hope for Marfan syndrome. Science 312 (2006) 36-37
    • (2006) Science , vol.312 , pp. 36-37
    • Travis, J.1
  • 4
    • 34548775221 scopus 로고    scopus 로고
    • Rationale and design of a randomized clinical trial of beta-blocker therapy (atenolol) versus angiotensin II receptor blocker therapy (losartan) in individuals with Marfan syndrome
    • Lacro R.V., Dietz H.C., Wruck L.M., Bradley T.J., Colan S.D., Devereux R.B., et al. Rationale and design of a randomized clinical trial of beta-blocker therapy (atenolol) versus angiotensin II receptor blocker therapy (losartan) in individuals with Marfan syndrome. Am Heart J 154 (2007) 624-631
    • (2007) Am Heart J , vol.154 , pp. 624-631
    • Lacro, R.V.1    Dietz, H.C.2    Wruck, L.M.3    Bradley, T.J.4    Colan, S.D.5    Devereux, R.B.6
  • 5
    • 0026492673 scopus 로고
    • Pharmacological profile of GR117289 in vitro: a novel, potent and specific non-peptide angiotensin AT1 receptor antagonist
    • Robertson M.J., Barnes J.C., Drew G.M., Clark K.L., Marshall F.H., Michel A., et al. Pharmacological profile of GR117289 in vitro: a novel, potent and specific non-peptide angiotensin AT1 receptor antagonist. Br J Pharmacol 107 (1992) 1173-1180
    • (1992) Br J Pharmacol , vol.107 , pp. 1173-1180
    • Robertson, M.J.1    Barnes, J.C.2    Drew, G.M.3    Clark, K.L.4    Marshall, F.H.5    Michel, A.6
  • 7
    • 0026561612 scopus 로고
    • The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices
    • Stearns R.A., Miller R.R., Doss G.A., Chakravarty P.K., Rosegay A., Gatto G.J., et al. The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices. Drug Metab Dispos 20 (1992) 281-287
    • (1992) Drug Metab Dispos , vol.20 , pp. 281-287
    • Stearns, R.A.1    Miller, R.R.2    Doss, G.A.3    Chakravarty, P.K.4    Rosegay, A.5    Gatto, G.J.6
  • 8
    • 16444378183 scopus 로고    scopus 로고
    • Candesartan cilexetil: a review of its use in the management of chronic heart failure
    • Fenton C., and Scott L.J. Candesartan cilexetil: a review of its use in the management of chronic heart failure. Drugs 65 (2005) 537-558
    • (2005) Drugs , vol.65 , pp. 537-558
    • Fenton, C.1    Scott, L.J.2
  • 9
    • 0029894243 scopus 로고    scopus 로고
    • Disposition of the new angiotensin II receptor antagonist candesartan cilexetil in rats and dogs
    • Kondo T., Yoshida K., Yoshimura Y., Motohashi M., and Tanayama S. Disposition of the new angiotensin II receptor antagonist candesartan cilexetil in rats and dogs. Arzneimittelforschung 46 (1996) 594-600
    • (1996) Arzneimittelforschung , vol.46 , pp. 594-600
    • Kondo, T.1    Yoshida, K.2    Yoshimura, Y.3    Motohashi, M.4    Tanayama, S.5
  • 10
    • 0029781981 scopus 로고    scopus 로고
    • Characterization of conjugated metabolites of a new angiotensin II receptor antagonist, candesartan cilexetil, in rats by liquid chromatography/electrospray tandem mass spectrometry following chemical derivatization
    • Kondo T., Yoshida K., Yoshimura Y., Motohashi M., and Tanayama S. Characterization of conjugated metabolites of a new angiotensin II receptor antagonist, candesartan cilexetil, in rats by liquid chromatography/electrospray tandem mass spectrometry following chemical derivatization. J Mass Spectrom 31 (1996) 873-878
    • (1996) J Mass Spectrom , vol.31 , pp. 873-878
    • Kondo, T.1    Yoshida, K.2    Yoshimura, Y.3    Motohashi, M.4    Tanayama, S.5
  • 13
    • 0034534895 scopus 로고    scopus 로고
    • Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions
    • Ritter J.K. Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 129 (2000) 171-193
    • (2000) Chem Biol Interact , vol.129 , pp. 171-193
    • Ritter, J.K.1
  • 14
    • 0034128936 scopus 로고    scopus 로고
    • Human UDP-glucuronosyltransferases: metabolism, expression, and disease
    • Tukey R.H., and Strassburg C.P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40 (2000) 581-616
    • (2000) Annu Rev Pharmacol Toxicol , vol.40 , pp. 581-616
    • Tukey, R.H.1    Strassburg, C.P.2
  • 15
    • 0347623265 scopus 로고    scopus 로고
    • The human UDP-glucuronosyltransferases: structural aspects and drug glucuronidation
    • Ouzzine M., Barre L., Netter P., Magdalou J., and Fournel-Gigleux S. The human UDP-glucuronosyltransferases: structural aspects and drug glucuronidation. Drug Metab Rev 35 (2003) 287-303
    • (2003) Drug Metab Rev , vol.35 , pp. 287-303
    • Ouzzine, M.1    Barre, L.2    Netter, P.3    Magdalou, J.4    Fournel-Gigleux, S.5
  • 16
    • 15244342411 scopus 로고    scopus 로고
    • UDP-glucuronosyltransferases and clinical drug-drug interactions
    • Kiang T.K., Ensom M.H., and Chang T.K. UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106 (2005) 97-132
    • (2005) Pharmacol Ther , vol.106 , pp. 97-132
    • Kiang, T.K.1    Ensom, M.H.2    Chang, T.K.3
  • 17
    • 0037819284 scopus 로고    scopus 로고
    • Pharmacogenomics of human UDP-glucuronosyltransferase enzymes
    • Guillemette C. Pharmacogenomics of human UDP-glucuronosyltransferase enzymes. Pharmacogenom J 3 (2003) 136-158
    • (2003) Pharmacogenom J , vol.3 , pp. 136-158
    • Guillemette, C.1
  • 20
    • 0025719938 scopus 로고
    • Synthesis and identification of a novel tetrazole metabolite of the angiotensin II receptor antagonist DuP 753
    • Stearns R.A., Doss G.A., Miller R.R., and Chiu S.H. Synthesis and identification of a novel tetrazole metabolite of the angiotensin II receptor antagonist DuP 753. Drug Metab Dispos 19 (1991) 1160-1162
    • (1991) Drug Metab Dispos , vol.19 , pp. 1160-1162
    • Stearns, R.A.1    Doss, G.A.2    Miller, R.R.3    Chiu, S.H.4
  • 21
    • 43249113309 scopus 로고    scopus 로고
    • Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan
    • Alonen A., Jansson J., Kallonen S., Kiriazis A., Aitio O., Finel M., et al. Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan. Bioorg Chem 36 (2008) 148-155
    • (2008) Bioorg Chem , vol.36 , pp. 148-155
    • Alonen, A.1    Jansson, J.2    Kallonen, S.3    Kiriazis, A.4    Aitio, O.5    Finel, M.6
  • 22
    • 0027451525 scopus 로고
    • N-Glucuronidation reaction. I. Tetrazole N-glucuronidation of selected angiotensin II receptor antagonists in hepatic microsomes from rats, dogs, monkeys, and humans
    • Huskey S.W., Miller R.R., and Chiu S.H.L. N-Glucuronidation reaction. I. Tetrazole N-glucuronidation of selected angiotensin II receptor antagonists in hepatic microsomes from rats, dogs, monkeys, and humans. Drug Metab Dispos 21 (1993) 792-799
    • (1993) Drug Metab Dispos , vol.21 , pp. 792-799
    • Huskey, S.W.1    Miller, R.R.2    Chiu, S.H.L.3
  • 23
    • 0029021205 scopus 로고
    • Absorption and glucuronidation of the angiotensin II receptor antagonist losartan by the rat intestine
    • Krieter P.A., Colletti A.E., Miller R.R., and Stearns R.A. Absorption and glucuronidation of the angiotensin II receptor antagonist losartan by the rat intestine. J Pharmacol Exp Ther 273 (1995) 816-822
    • (1995) J Pharmacol Exp Ther , vol.273 , pp. 816-822
    • Krieter, P.A.1    Colletti, A.E.2    Miller, R.R.3    Stearns, R.A.4
  • 24
    • 33847043537 scopus 로고    scopus 로고
    • Interactions with other human UDP-glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6
    • Kurkela M., Patana A.S., Mackenzie P.I., Court M.H., Tate C.G., Hirvonen J., et al. Interactions with other human UDP-glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6. Pharmacogenet Genom 17 (2007) 115-126
    • (2007) Pharmacogenet Genom , vol.17 , pp. 115-126
    • Kurkela, M.1    Patana, A.S.2    Mackenzie, P.I.3    Court, M.H.4    Tate, C.G.5    Hirvonen, J.6
  • 25
    • 0030895678 scopus 로고    scopus 로고
    • Characterization of 1-hydroxypyrene as a novel marker substrate of 3-methylcholanthrene-inducible phenol UDP-glucuronosyltransferase(s)
    • Luukkanen L., Elovaara E., Lautala P., Taskinen J., and Vainio H. Characterization of 1-hydroxypyrene as a novel marker substrate of 3-methylcholanthrene-inducible phenol UDP-glucuronosyltransferase(s). Pharmacol Toxicol 80 (1997) 152-158
    • (1997) Pharmacol Toxicol , vol.80 , pp. 152-158
    • Luukkanen, L.1    Elovaara, E.2    Lautala, P.3    Taskinen, J.4    Vainio, H.5
  • 26
    • 0035111915 scopus 로고    scopus 로고
    • Characterization of 2-[[4-[[2-(1H-tetrazol-5-ylmethyl)phenyl]methoxy]methyl]quinoline N-glucuronidation by in vitro and in vivo approaches
    • Stevens J.C., Fayer J.L., and Cassidy K.C. 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 (2001) 289-295
    • (2001) Drug Metab Dispos , vol.29 , pp. 289-295
    • Stevens, J.C.1    Fayer, J.L.2    Cassidy, K.C.3
  • 27
    • 0031765698 scopus 로고    scopus 로고
    • Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3
    • Green M.D., King C.D., Mojarrabi B., Mackenzie P.I., and Tephly T.R. Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26 (1998) 507-512
    • (1998) Drug Metab Dispos , vol.26 , pp. 507-512
    • Green, M.D.1    King, C.D.2    Mojarrabi, B.3    Mackenzie, P.I.4    Tephly, T.R.5
  • 28
    • 0031706608 scopus 로고    scopus 로고
    • Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins
    • Green M.D., and Tephly T.R. Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins. Drug Metab Dispos 26 (1998) 860-867
    • (1998) Drug Metab Dispos , vol.26 , pp. 860-867
    • Green, M.D.1    Tephly, T.R.2
  • 29
    • 11144271522 scopus 로고    scopus 로고
    • Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s)
    • Kaji H., and Kume T. Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). Drug Metab Dispos 33 (2005) 60-67
    • (2005) Drug Metab Dispos , vol.33 , pp. 60-67
    • Kaji, H.1    Kume, T.2
  • 30
    • 0034829104 scopus 로고    scopus 로고
    • Quaternary ammonium-linked glucuronidation of 1-substituted imidazoles: studies of human UDP-glucuronosyltransferases involved and substrate specificities
    • Vashishtha S.C., Hawes E.M., McKay G., and McCann D.J. Quaternary ammonium-linked glucuronidation of 1-substituted imidazoles: studies of human UDP-glucuronosyltransferases involved and substrate specificities. Drug Metab Dispos 29 (2001) 1290-1295
    • (2001) Drug Metab Dispos , vol.29 , pp. 1290-1295
    • Vashishtha, S.C.1    Hawes, E.M.2    McKay, G.3    McCann, D.J.4
  • 31
    • 0036266825 scopus 로고    scopus 로고
    • Imipramine N-glucuronidation in human liver microsomes: biphasic kinetics and characterization of UDP-glucuronosyltransferase isoforms
    • Nakajima M., Tanaka E., Kobayashi T., Ohashi N., Kume T., and Yokoi T. Imipramine N-glucuronidation in human liver microsomes: biphasic kinetics and characterization of UDP-glucuronosyltransferase isoforms. Drug Metab Dispos 30 (2002) 636-642
    • (2002) Drug Metab Dispos , vol.30 , pp. 636-642
    • Nakajima, M.1    Tanaka, E.2    Kobayashi, T.3    Ohashi, N.4    Kume, T.5    Yokoi, T.6
  • 32
    • 1642457368 scopus 로고    scopus 로고
    • Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol(NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4
    • Wiener D., Doerge D.R., Fang J.L., Upadhyaya P., and Lazarus P. Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol(NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4. Drug Metab Dispos 32 (2004) 72-79
    • (2004) Drug Metab Dispos , vol.32 , pp. 72-79
    • Wiener, D.1    Doerge, D.R.2    Fang, J.L.3    Upadhyaya, P.4    Lazarus, P.5
  • 33
    • 0036836947 scopus 로고    scopus 로고
    • 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods
    • Herr R.J. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg Med Chem 10 (2002) 3379-3393
    • (2002) Bioorg Med Chem , vol.10 , pp. 3379-3393
    • Herr, R.J.1
  • 36
    • 17844362183 scopus 로고    scopus 로고
    • Biosynthesis of dobutamine monoglucuronides and glucuronidation of dobutamine by recombinant human UDP-glucuronosyltransferases
    • Alonen A., Aitio O., Hakala K., Luukkanen L., Finel M., and Kostiainen R. Biosynthesis of dobutamine monoglucuronides and glucuronidation of dobutamine by recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos 33 (2005) 657-663
    • (2005) Drug Metab Dispos , vol.33 , pp. 657-663
    • Alonen, A.1    Aitio, O.2    Hakala, K.3    Luukkanen, L.4    Finel, M.5    Kostiainen, R.6
  • 38
    • 0037422456 scopus 로고    scopus 로고
    • Acyl glucuronide reactivity in perspective: biological consequences
    • Bailey M.J., and Dickinson R.G. Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 145 (2003) 117-137
    • (2003) Chem Biol Interact , vol.145 , pp. 117-137
    • Bailey, M.J.1    Dickinson, R.G.2
  • 39
    • 0034278933 scopus 로고    scopus 로고
    • Hepatic disposition of electrophilic acyl glucuronide conjugates
    • Sallustio B.C., Sabordo L., Evans A.M., and Nation R.L. Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab 1 (2000) 163-180
    • (2000) Curr Drug Metab , vol.1 , pp. 163-180
    • Sallustio, B.C.1    Sabordo, L.2    Evans, A.M.3    Nation, R.L.4
  • 40
    • 0037306174 scopus 로고    scopus 로고
    • Acyl glucuronide drug metabolites: toxicological and analytical implications
    • Shipkova M., Armstrong V.W., Oellerich M., and Wieland E. Acyl glucuronide drug metabolites: toxicological and analytical implications. Ther Drug Monit 25 (2003) 1-16
    • (2003) Ther Drug Monit , vol.25 , pp. 1-16
    • Shipkova, M.1    Armstrong, V.W.2    Oellerich, M.3    Wieland, E.4


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