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Volumn 17, Issue 1, 2012, Pages 851-860

Effect of efavirenz on UDP-glucuronosyltransferase 1A1, 1A4, 1A6, and 1A9 activities in human liver microsomes

Author keywords

Drug drug interaction; Efavirenz; Human liver microsomes; UDP glucuronosyltransferase inhibition

Indexed keywords

BENZOXAZINE DERIVATIVE; BILIRUBIN GLUCURONOSIDE GLUCURONOSYLTRANSFERASE; BILIRUBIN URIDINE DIPHOSPHOGLUCURONOSYL TRANSFERASE 1A1; BILIRUBIN URIDINE-DIPHOSPHOGLUCURONOSYL TRANSFERASE 1A1; EFAVIRENZ; ESTRADIOL; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A9; PROPOFOL; TRIFLUOPERAZINE; UDP GLUCURONOSYLTRANSFERASE, UGT1A6; UDP-GLUCURONOSYLTRANSFERASE 1A9; UDP-GLUCURONOSYLTRANSFERASE, UGT1A6;

EID: 84862916534     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010851     Document Type: Article
Times cited : (21)

References (35)
  • 2
    • 78549263792 scopus 로고    scopus 로고
    • Efavirenz/emtricitabine/tenofovir disoproxil fumarate single-tablet regimen (Atripla(R)): A review of its use in the management of HIV infection
    • Deeks, E.D.; Perry, C.M. Efavirenz/emtricitabine/tenofovir disoproxil fumarate single-tablet regimen (Atripla(R)): A review of its use in the management of HIV infection. Drugs 2010, 70, 2315-2338.
    • (2010) Drugs , vol.70 , pp. 2315-2338
    • Deeks, E.D.1    Perry, C.M.2
  • 3
    • 84862919908 scopus 로고    scopus 로고
    • U.S. Prescribing Information. Available online, (accessed on 1 December)
    • U.S. Prescribing Information. Available online: http://packageinserts. bms.com/pi/pi-sustiva.pdf (accessed on 1 December 2011).
    • (2011)
  • 4
    • 0032589627 scopus 로고    scopus 로고
    • Identification and characterization of efavirenz metabolites by liquid chromatography/mass spectrometry and high field NMR: Species differences in the metabolism of efavirenz
    • Mutlib, A.E.; Chen, H.; Nemeth, G.A.; Markwalder, J.A.; Seitz, S.P.; Gan, L.S.; Christ, D.D. Identification and characterization of efavirenz metabolites by liquid chromatography/mass spectrometry and high field NMR: Species differences in the metabolism of efavirenz. Drug Metab. Dispos. 1999, 27, 1319-1333.
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 1319-1333
    • Mutlib, A.E.1    Chen, H.2    Nemeth, G.A.3    Markwalder, J.A.4    Seitz, S.P.5    Gan, L.S.6    Christ, D.D.7
  • 5
    • 0038002981 scopus 로고    scopus 로고
    • The cytochrome P450 2B6 (CYP2B6) is the main catalyst of efavirenz primary and secondary metabolism: Implication for HIV/AIDS therapy and utility of efavirenz as a substrate marker of CYP2B6 catalytic activity
    • DOI 10.1124/jpet.103.049601
    • Ward, B.A.; Gorski, J.C.; Jones, D.R.; Hall, S.D.; Flockhart, D.A.; Desta, Z. The cytochrome P450 2B6 (CYP2B6) is the main catalyst of efavirenz primary and secondary metabolism: Implication for HIV/AIDS therapy and utility of efavirenz as a substrate marker of CYP2B6 catalytic activity. J. Pharmacol. Exp. Ther. 2003, 306, 287-300. (Pubitemid 36734384)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.306 , Issue.1 , pp. 287-300
    • Ward, B.A.1    Gorski, J.C.2    Jones, D.R.3    Hall, S.D.4    Flockhart, D.A.5    Desta, Z.6
  • 6
    • 77953756056 scopus 로고    scopus 로고
    • Efavirenz primary and secondary metabolism in vitro and in vivo: Identification of novel metabolic pathways and cytochrome P450 2A6 as the principal catalyst of efavirenz 7-hydroxylation
    • Ogburn, E.T.; Jones, D.R.; Masters, A.R.; Xu, C.; Guo, Y.; Desta, Z. Efavirenz primary and secondary metabolism in vitro and in vivo: Identification of novel metabolic pathways and cytochrome P450 2A6 as the principal catalyst of efavirenz 7-hydroxylation. Drug Metab. Dispos. 2010, 38, 1218-1229.
    • (2010) Drug Metab. Dispos. , vol.38 , pp. 1218-1229
    • Ogburn, E.T.1    Jones, D.R.2    Masters, A.R.3    Xu, C.4    Guo, Y.5    Desta, Z.6
  • 7
    • 79952607777 scopus 로고    scopus 로고
    • In silico prediction of efavirenz and rifampicin drug-drug interaction considering weight and CYP2B6 phenotype
    • Rekic, D.; Roshammar, D.; Mukonzo, J.; Ashton, M. In silico prediction of efavirenz and rifampicin drug-drug interaction considering weight and CYP2B6 phenotype. Br. J. Clin. Pharmacol. 2011, 71, 536-543.
    • (2011) Br. J. Clin. Pharmacol. , vol.71 , pp. 536-543
    • Rekic, D.1    Roshammar, D.2    Mukonzo, J.3    Ashton, M.4
  • 8
    • 79956364942 scopus 로고    scopus 로고
    • Identification of human UGT isoforms responsible for glucuronidation of efavirenz and its three hydroxy metabolites
    • Bae, S.K.; Jeong, Y.J.; Lee, C.; Liu, K.H. Identification of human UGT isoforms responsible for glucuronidation of efavirenz and its three hydroxy metabolites. Xenobiotica 2011, 41, 437-444.
    • (2011) Xenobiotica , vol.41 , pp. 437-444
    • Bae, S.K.1    Jeong, Y.J.2    Lee, C.3    Liu, K.H.4
  • 9
    • 79953171166 scopus 로고    scopus 로고
    • Contribution of N-glucuronidation to efavirenz elimination in vivo in the basal and rifampin-induced metabolism of efavirenz
    • Cho, D.Y.; Ogburn, E.T.; Jones, D.; Desta, Z. Contribution of N-glucuronidation to efavirenz elimination in vivo in the basal and rifampin-induced metabolism of efavirenz. Antimicrob. Agents Chemother. 2011, 55, 1504-1509.
    • (2011) Antimicrob. Agents Chemother. , vol.55 , pp. 1504-1509
    • Cho, D.Y.1    Ogburn, E.T.2    Jones, D.3    Desta, Z.4
  • 10
    • 70349108450 scopus 로고    scopus 로고
    • Glucuronidation of the antiretroviral drug efavirenz by UGT2B7 and an in vitro investigation of drug-drug interaction with zidovudine
    • Belanger, A.S.; Caron, P.; Harvey, M.; Zimmerman, P.A.; Mehlotra, R.K.; Guillemette, C. Glucuronidation of the antiretroviral drug efavirenz by UGT2B7 and an in vitro investigation of drug-drug interaction with zidovudine. Drug Metab. Dispos. 2009, 37, 1793-1796.
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1793-1796
    • Belanger, A.S.1    Caron, P.2    Harvey, M.3    Zimmerman, P.A.4    Mehlotra, R.K.5    Guillemette, C.6
  • 13
    • 58149467072 scopus 로고    scopus 로고
    • Determination of mRNA expression of human UDP-glucuronosyl transferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction
    • Ohno, S.; Nakajin, S. Determination of mRNA expression of human UDP-glucuronosyl transferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction. Drug Metab. Dispos. 2009, 7, 32-40.
    • (2009) Drug Metab. Dispos. , vol.7 , pp. 32-40
    • Ohno, S.1    Nakajin, S.2
  • 14
    • 15244342411 scopus 로고    scopus 로고
    • UDP-glucuronosyltransferases and clinical drug-drug interactions
    • DOI 10.1016/j.pharmthera.2004.10.013
    • Kiang, T.K.; Ensom, M.H.; Chang, T.K. UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol. Ther. 2005, 106, 97-132. (Pubitemid 40386722)
    • (2005) Pharmacology and Therapeutics , vol.106 , Issue.1 , pp. 97-132
    • Kiang, T.K.L.1    Ensom, M.H.H.2    Chang, T.K.H.3
  • 15
    • 79952479196 scopus 로고    scopus 로고
    • Effects of herbal supplements on drug glucuronidation. Review of clinical, animal, and in vitro studies
    • Mohamed, M.F.; Frye, R.F. Effects of herbal supplements on drug glucuronidation. Review of clinical, animal, and in vitro studies. Planta Med. 2011, 77, 311-321.
    • (2011) Planta Med. , vol.77 , pp. 311-321
    • Mohamed, M.F.1    Frye, R.F.2
  • 16
    • 0033926065 scopus 로고    scopus 로고
    • Effects of rifampicin and cimetidine on pharmacokinetics and pharmacodynamics of lamotrigine in healthy subjects
    • Ebert, U.; Thong, N.Q.; Qertel, R.; Kirch, W. Effects of rifampicin and cimetidine on pharmacokinetics and pharmacodynamics of lamotrigine in healthy subjects. Eur. J. Clin. Pharmacol. 2000, 56, 299-304. (Pubitemid 30462927)
    • (2000) European Journal of Clinical Pharmacology , vol.56 , Issue.4 , pp. 299-304
    • Ebert, U.1    Thong, N.Q.2    Oertel, R.3    Kirch, W.4
  • 18
    • 33344473930 scopus 로고    scopus 로고
    • Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline androsterone canrenoic acid hecogenin phenylbutazone quinidine quinine and sulfinpyrazone) "probes" for human UDP-glucuronosyltransferases
    • Uchaipichat, V.; Mackenzie, P.I.; Elliot, D.J.; Miners, J.O. Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human UDP-glucuronosyltransferases. Drug Metab. Dispos. 2006, 34, 449-456.
    • (2006) Drug Metab. Dispos. , vol.34 , pp. 449-456
    • Uchaipichat, V.1    Mackenzie, P.I.2    Elliot, D.J.3    Miners, J.O.4
  • 19
    • 30144436526 scopus 로고    scopus 로고
    • Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases
    • DOI 10.1016/S0076-6879(05)00007-8, PII S0076687905000078, 7, Phase II Conjugation Enzymes and Transport Systems
    • Court, M.H. Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases. Methods Enzymol. 2005, 400, 104-116. (Pubitemid 43052418)
    • (2005) Methods in Enzymology , vol.400 , pp. 104-116
    • Court, M.H.1
  • 20
    • 77951296034 scopus 로고    scopus 로고
    • Validated assay for studying activity profiles of human liver UGTs after drug exposure: Inhibition and induction studies
    • Donato, M.T.; Montero, S.; Castell, J.V.; Gómez-Lechón, M.J.; Lahoz, A. Validated assay for studying activity profiles of human liver UGTs after drug exposure: Inhibition and induction studies. Anal. Bioanal. Chem. 2010, 96, 2251-2263.
    • (2010) Anal. Bioanal. Chem. , vol.96 , pp. 2251-2263
    • Donato, M.T.1    Montero, S.2    Castell, J.V.3    Gómez-Lechón, M.J.4    Lahoz, A.5
  • 21
    • 80052230944 scopus 로고    scopus 로고
    • Corydaline inhibits multiple cytochrome P450 and UDP- glucuronosyltransferase enzyme activities in human liver microsomes
    • Ji, H.Y.; Liu, K.H.; Lee, H.; Im, S.R.; Shim, H.J.; Son, M.; Lee, H.S. Corydaline inhibits multiple cytochrome P450 and UDP-glucuronosyltransferase enzyme activities in human liver microsomes. Molecules 2011, 16, 6591-6602.
    • (2011) Molecules , vol.16 , pp. 6591-6602
    • Ji, H.Y.1    Liu, K.H.2    Lee, H.3    Im, S.R.4    Shim, H.J.5    Son, M.6    Lee, H.S.7
  • 22
    • 0035875828 scopus 로고    scopus 로고
    • Efavirenz plasma levels can predict treatment failure and central nervous system side effects in HIV-1-infected patients
    • DOI 10.1097/00002030-200101050-00011
    • Marzolini, C.; Telenti, A.; Decosterd, L.A.; Greub, G.; Biollaz, J.; Buclin, T. Efavirenz plasma levels can predict treatment failure and central nervous system side effects in HIV-1-infected patients. AIDS 2001, 15, 71-75. (Pubitemid 32055781)
    • (2001) AIDS , vol.15 , Issue.1 , pp. 71-75
    • Marzolini, C.1    Telenti, A.2    Decosterd, L.A.3    Greub, G.4    Biollaz, J.5    Buclin, T.6
  • 23
    • 77952314576 scopus 로고    scopus 로고
    • Investigation into UDP-glucuronosyltransferase (UGT) enzyme kinetics of imidazole- and triazole-containing antifungal drugs in human liver microsomes and recombinant UGT enzymes
    • Bourcier, K.; Hyland, R.; Kempshall, S.; Jones, R.; Maximilien, J.; Irvine, N.; Jones, B. Investigation into UDP-glucuronosyltransferase (UGT) enzyme kinetics of imidazole- and triazole-containing antifungal drugs in human liver microsomes and recombinant UGT enzymes. Drug Metab. Dispos. 2010, 38, 923-929.
    • (2010) Drug Metab. Dispos. , vol.38 , pp. 923-929
    • Bourcier, K.1    Hyland, R.2    Kempshall, S.3    Jones, R.4    Maximilien, J.5    Irvine, N.6    Jones, B.7
  • 25
    • 2342572781 scopus 로고    scopus 로고
    • Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4
    • DOI 10.1016/j.bcp.2004.02.014, PII S0006295204001285
    • Kaku, T.; Ogura, K.; Nishiyama, T.; Ohnuma, T.; Muro, K.; Hiratsuka, A. Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochem. Pharmacol. 2004, 67, 2093-2102. (Pubitemid 38595490)
    • (2004) Biochemical Pharmacology , vol.67 , Issue.11 , pp. 2093-2102
    • Kaku, T.1    Ogura, K.2    Nishiyama, T.3    Ohnuma, T.4    Muro, K.5    Hiratsuka, A.6
  • 26
    • 33646784394 scopus 로고    scopus 로고
    • In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction
    • DOI 10.1124/dmd.106.009340
    • Rowland, A.; Elliot, D.J.; Williams, J.A.; Mackenzie, P.I.; Dickinson, R.G.; Miners, J.O. In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction. Drug Metab. Dispos. 2006, 34, 1055-1062. (Pubitemid 43763765)
    • (2006) Drug Metabolism and Disposition , vol.34 , Issue.6 , pp. 1055-1062
    • Rowland, A.1    Elliot, D.J.2    Williams, J.A.3    Mackenzie, P.I.4    Dickinson, R.G.5    Miners, J.O.6
  • 27
    • 79959453365 scopus 로고    scopus 로고
    • In vitro investigation of human UDP-glucuronosyltransferase isoforms responsible for tacrolimus glucuronidation: Predominant contribution of UGT1A4
    • Laverdiere, I.; Caron, P.; Harvey, M.; Levesque, E.; Guillemette, C. In vitro investigation of human UDP-glucuronosyltransferase isoforms responsible for tacrolimus glucuronidation: Predominant contribution of UGT1A4. Drug Metab. Dispos. 2011, 39, 1127-1130.
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 1127-1130
    • Laverdiere, I.1    Caron, P.2    Harvey, M.3    Levesque, E.4    Guillemette, C.5
  • 28
    • 79952819517 scopus 로고    scopus 로고
    • Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: Application to the reaction phenotyping of acetaminophen glucuronidation
    • Miners, J.O.; Bowalgaha, K.; Elliot, D.J.; Baranczewski, P.; Knights, K.M. Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: Application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab. Dispos. 2011, 39, 644-652.
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 644-652
    • Miners, J.O.1    Bowalgaha, K.2    Elliot, D.J.3    Baranczewski, P.4    Knights, K.M.5
  • 29
    • 31744443743 scopus 로고    scopus 로고
    • In vitro inhibitory effects of non-steroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP- glucuronosyltransferase 1A9 - Potent inhibition by niflumic acid
    • DOI 10.1002/bdd.475
    • Mano, Y.; Usui, T.; Kamimura, H. In vitro inhibitory effects of non-steroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP-glucuronosyltransferase 1A9-potent inhibition by niflumic acid. Biopharm. Drug Dispos. 2006, 27, 1-6. (Pubitemid 43173968)
    • (2006) Biopharmaceutics and Drug Disposition , vol.27 , Issue.1 , pp. 1-6
    • Mano, Y.1    Usui, T.2    Kamimura, H.3
  • 31
    • 3142512630 scopus 로고    scopus 로고
    • Stereoselectlve glucuronidation and hydroxylation of etodolac by UGT1A9 and CYP2C9 in man
    • DOI 10.1080/00498250410001691280
    • Tougou, K.; Gotou, H.; Ohno, Y.; Nakamura, A. Stereoselective glucuronidation and hydroxylation of etodolac by UGT1A9 and CYP2C9 in man. Xenobiotica 2004, 34, 449-461. (Pubitemid 38901455)
    • (2004) Xenobiotica , vol.34 , Issue.5 , pp. 449-461
    • Tougou, K.1    Gotou, H.2    Ohno, Y.3    Nakamura, A.4
  • 32
    • 0033786733 scopus 로고    scopus 로고
    • The specificity of glucuronidation of entacapone and tolcapone by recombinant human UDP-glucuronosyltransferases
    • Lautala, P.; Ethell, B.T.; Taskinen, J.; Burchell, B. The specificity of glucuronidation of entacapone and tolcapone by recombinant human UDP-glucuronosyltransferases. Drug Metab. Dispos. 2000, 28, 1385-1389.
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 1385-1389
    • Lautala, P.1    Ethell, B.T.2    Taskinen, J.3    Burchell, B.4
  • 34
    • 33646497843 scopus 로고    scopus 로고
    • 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
    • Borlak, J.; Gasparic, A.; Locher, M.; Schupke, H.; Hermann, R. 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. Metabolism 2006, 55, 711-721.
    • (2006) Metabolism , vol.55 , pp. 711-721
    • Borlak, J.1    Gasparic, A.2    Locher, M.3    Schupke, H.4    Hermann, R.5
  • 35
    • 18144406492 scopus 로고    scopus 로고
    • Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases
    • DOI 10.1124/dmd.105.004093
    • Luukkanen, L.; Taskinen, J.; Kurkela, M.; Kostiainen, R.; Hirvonen, J.; Finel, M. Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. Drug Metab. Dispos. 2005, 33, 1017-1026. (Pubitemid 41002784)
    • (2005) Drug Metabolism and Disposition , vol.33 , Issue.7 , pp. 1017-1026
    • Luukkanen, L.1    Taskinen, J.2    Kurkela, M.3    Kostiainen, R.4    Hirvonen, J.5    Finel, M.6


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