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Volumn 30, Issue 12, 2002, Pages 1478-1483

Microsomal N-glucuronidation of nicotine and cotinine: Human hepatic interindividual, human intertissue, and interspecies hepatic variation

Author keywords

[No Author keywords available]

Indexed keywords

COTININE; GLUCURONOSYLTRANSFERASE; NICOTINE; URIDINE DIPHOSPHATE GLUCURONIC ACID;

EID: 0036893113     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.30.12.1478     Document Type: Article
Times cited : (26)

References (38)
  • 1
    • 0034124565 scopus 로고    scopus 로고
    • Effects of cigarette smoking and carbon monoxide on nicotine and cotinine metabolism
    • Benowitz NL and Jacob P III (2000) Effects of cigarette smoking and carbon monoxide on nicotine and cotinine metabolism. Clin Pharmacol Ther 67:653-659.
    • (2000) Clin Pharmacol Ther , vol.67 , pp. 653-659
    • Benowitz, N.L.1    Jacob P. III2
  • 2
    • 0027958225 scopus 로고
    • Nicotine metabolic profile in man: Comparison of cigarette smoking and transdermal nicotine
    • Benowitz NL, Jacob P III, Fong I, and Gupta S (1994) Nicotine metabolic profile in man: Comparison of cigarette smoking and transdermal nicotine. J Pharmacol Exp Ther 268:296-303.
    • (1994) J Pharmacol Exp Ther , vol.268 , pp. 296-303
    • Benowitz, N.L.1    Jacob P. III2    Fong, I.3    Gupta, S.4
  • 4
    • 0026586611 scopus 로고
    • Evidence for urinary excretion of glucuronide conjugates of nicotine, cotinine and trans-3′-hydroxycotinine in smokers
    • Byrd GD, Chang K-M, Greene JM, and deBethizy JD (1992) Evidence for urinary excretion of glucuronide conjugates of nicotine, cotinine and trans-3′-hydroxycotinine in smokers. Drug Metab Dispos 20:192-197.
    • (1992) Drug Metab Dispos , vol.20 , pp. 192-197
    • Byrd, G.D.1    Chang, K.-M.2    Greene, J.M.3    DeBethizy, J.D.4
  • 6
    • 0031704509 scopus 로고    scopus 로고
    • Species differences in N-glucuronidation
    • Chiu S-HL and Huskey S-EW (1998) Species differences in N-glucuronidation. Drug Metab Dispos 26:838-847.
    • (1998) Drug Metab Dispos , vol.26 , pp. 838-847
    • Chiu, S.-H.L.1    Huskey, S.-E.W.2
  • 7
    • 0035197725 scopus 로고    scopus 로고
    • Interindividual variability in acetaminophen glucuronidation by human liver microsomes: Identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms
    • Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, and Mackenzie PI (2001) Interindividual variability in acetaminophen glucuronidation by human liver microsomes: Identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther 299:998-1006.
    • (2001) J Pharmacol Exp Ther , vol.299 , pp. 998-1006
    • Court, M.H.1    Duan, S.X.2    Von Moltke, L.L.3    Greenblatt, D.J.4    Patten, C.J.5    Miners, J.O.6    Mackenzie, P.I.7
  • 8
    • 0035209568 scopus 로고    scopus 로고
    • The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism
    • Fisher MB, Paine MF, Strelevitz TJ, and Wrighton SA (2001) The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metab Rev 33:273-297.
    • (2001) Drug Metab Rev , vol.33 , pp. 273-297
    • Fisher, M.B.1    Paine, M.F.2    Strelevitz, T.J.3    Wrighton, S.A.4
  • 9
    • 0032937925 scopus 로고    scopus 로고
    • Glucuronidation of drugs by hepatic microsomes derived from healthy and cirrhotic human livers
    • Furlan V, Demirdjian S, Bourdon O, Magdalou J, and Taburet A-M (1999) Glucuronidation of drugs by hepatic microsomes derived from healthy and cirrhotic human livers. J Pharmacol Exp Ther 289:1169-1175.
    • (1999) J Pharmacol Exp Ther , vol.289 , pp. 1169-1175
    • Furlan, V.1    Demirdjian, S.2    Bourdon, O.3    Magdalou, J.4    Taburet, A.-M.5
  • 10
    • 0036707617 scopus 로고    scopus 로고
    • N-Glucuronidation of nicotine and cotinine in human: Formation of cotinine glucuronide in liver microsomes and lack of catalysis by ten examined UDP-glucuronosyltransferases
    • Ghosheh O and Hawes EM (2002) N-Glucuronidation of nicotine and cotinine in human: Formation of cotinine glucuronide in liver microsomes and lack of catalysis by ten examined UDP-glucuronosyltransferases. Drug Metab Dispos 30:991-996.
    • (2002) Drug Metab Dispos , vol.30 , pp. 991-996
    • Ghosheh, O.1    Hawes, E.M.2
  • 11
    • 0035193376 scopus 로고    scopus 로고
    • Formation of the quaternary ammoniumlinked glucuronide of nicotine in human liver microsomes: Identification and stereoselectivity in the kinetics
    • Ghosheh O, Vashishtha SC, and Hawes EM (2001) Formation of the quaternary ammoniumlinked glucuronide of nicotine in human liver microsomes: Identification and stereoselectivity in the kinetics. Drug Metab Dispos 29:1525-1528.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1525-1528
    • Ghosheh, O.1    Vashishtha, S.C.2    Hawes, E.M.3
  • 12
    • 0028948889 scopus 로고
    • Expressed human UGT1.4 protein catalyzes the formation of quaternary ammonium-linked glucuronides
    • Green MD, Bishop WP, and Tephly TR (1995) Expressed human UGT1.4 protein catalyzes the formation of quaternary ammonium-linked glucuronides. Drug Metab Dispos 23:299-302.
    • (1995) Drug Metab Dispos , vol.23 , pp. 299-302
    • Green, M.D.1    Bishop, W.P.2    Tephly, T.R.3
  • 13
    • 0031765698 scopus 로고    scopus 로고
    • Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3
    • Green MD, King CD, Mojarrabi B, Mackenzie PI, and Tephly TR (1998) Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26:507-512.
    • (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
  • 14
    • 0029962074 scopus 로고    scopus 로고
    • Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein
    • Green MD and Tephly TR (1996) Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug Metab Dispos 24:356-363.
    • (1996) Drug Metab Dispos , vol.24 , pp. 356-363
    • Green, M.D.1    Tephly, T.R.2
  • 16
    • 0033388771 scopus 로고    scopus 로고
    • CYP2A6 genetic polymorphisms and liver microsomal coumarin and nicotine oxidation activities in Japanese and Caucasians
    • Inoue K, Yamazaki H, and Shimada T (2000) CYP2A6 genetic polymorphisms and liver microsomal coumarin and nicotine oxidation activities in Japanese and Caucasians. Arch Toxicol 73:532-539.
    • (2000) Arch Toxicol , vol.73 , pp. 532-539
    • Inoue, K.1    Yamazaki, H.2    Shimada, T.3
  • 18
    • 0020541055 scopus 로고
    • Quaternary ammonium-linked glucuronides of amitriptyline, imipramine, and chlorpromazine
    • Lehman JP, Fenselau C, and dePaulo JR (1983) Quaternary ammonium-linked glucuronides of amitriptyline, imipramine, and chlorpromazine. Drug Metab Dispos 11:221-225.
    • (1983) Drug Metab Dispos , vol.11 , pp. 221-225
    • Lehman, J.P.1    Fenselau, C.2    DePaulo, J.R.3
  • 22
    • 0032055273 scopus 로고    scopus 로고
    • Drug glucuronidation by human renal UDP-glucuronosyltransferases
    • McGurk KA, Brierley CH, and Burchell B (1998) Drug glucuronidation by human renal UDP-glucuronosyltransferases. Biochem Pharmacol 55:1005-1012.
    • (1998) Biochem Pharmacol , vol.55 , pp. 1005-1012
    • McGurk, K.A.1    Brierley, C.H.2    Burchell, B.3
  • 24
    • 0035154274 scopus 로고    scopus 로고
    • Genetic polymorphisms in the cytochrome P450 2A6 (CYP2A6) gene: Implications for interindividual differences in nicotine metabolism
    • Oscarson M (2001) Genetic polymorphisms in the cytochrome P450 2A6 (CYP2A6) gene: Implications for interindividual differences in nicotine metabolism. Drug Metab Dispos 29:91-95.
    • (2001) Drug Metab Dispos , vol.29 , pp. 91-95
    • Oscarson, M.1
  • 26
    • 0025893724 scopus 로고
    • A quaternary ammonium glucuronide is the major metabolite of lamotrigine in guinea pigs, in vitro and in vivo studies
    • Remmel RP and Sinz MW (1991) A quaternary ammonium glucuronide is the major metabolite of lamotrigine in guinea pigs, in vitro and in vivo studies. Drug Metab Dispos 19:630-636.
    • (1991) Drug Metab Dispos , vol.19 , pp. 630-636
    • Remmel, R.P.1    Sinz, M.W.2
  • 27
    • 0027378475 scopus 로고
    • Rates of excretion of cotinine, nicotine glucuronide, and 3-hydroxycotinine glucuronide in rat bile
    • Seaton MJ, Kyerematen GA, and Vesell ES (1993b) Rates of excretion of cotinine, nicotine glucuronide, and 3-hydroxycotinine glucuronide in rat bile. Drug Metab Dispos 21:927-932.
    • (1993) Drug Metab Dispos , vol.21 , pp. 927-932
    • Seaton, M.J.1    Kyerematen, G.A.2    Vesell, E.S.3
  • 28
    • 0027525449 scopus 로고
    • Identification of radiolabeled metabolites of nicotine in rat bile, synthesis of S-(-)-nicotine N-glucuronide, and direct separation of nicotine-derived conjugates using high-performance liquid chromatography
    • Seaton MJ, Vesell ES, Luo H, and Hawes EM (1993a) Identification of radiolabeled metabolites of nicotine in rat bile, synthesis of S-(-)-nicotine N-glucuronide, and direct separation of nicotine-derived conjugates using high-performance liquid chromatography. J Chromatogr 621:49-53.
    • (1993) J Chromatogr , vol.621 , pp. 49-53
    • Seaton, M.J.1    Vesell, E.S.2    Luo, H.3    Hawes, E.M.4
  • 30
    • 0035692560 scopus 로고    scopus 로고
    • Evaluation of the marmoset as a model species for drug glucuronidation
    • Soars MG, Riley RJ, and Burchell B (2001a) Evaluation of the marmoset as a model species for drug glucuronidation. Xenobiotica 31:849-860.
    • (2001) Xenobiotica , vol.31 , pp. 849-860
    • Soars, M.G.1    Riley, R.J.2    Burchell, B.3
  • 31
    • 0035154231 scopus 로고    scopus 로고
    • Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney
    • Soars MG, Riley RJ, Findlay KAB, Coffey MJ, and Burchell B (2001b) Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug Metab Dispos 29:121-126.
    • (2001) Drug Metab Dispos , vol.29 , pp. 121-126
    • Soars, M.G.1    Riley, R.J.2    Findlay, K.A.B.3    Coffey, M.J.4    Burchell, B.5
  • 32
    • 0034680792 scopus 로고    scopus 로고
    • Polymorphic gene regulation and interindividual variation of UDP-glucuronosyltransferase activity in human small intestine
    • Strassburg CP, Kneip S, Topp J, Obermayer-Straub P, Barut A, Tukey RH, and Manns MP (2000) Polymorphic gene regulation and interindividual variation of UDP-glucuronosyltransferase activity in human small intestine. J Biol Chem 275:36164-36171.
    • (2000) J Biol Chem , vol.275 , pp. 36164-36171
    • Strassburg, C.P.1    Kneip, S.2    Topp, J.3    Obermayer-Straub, P.4    Barut, A.5    Tukey, R.H.6    Manns, M.P.7
  • 33
  • 34
    • 0032701917 scopus 로고    scopus 로고
    • Evidence for the biosynthesis of a glucuronide conjugate of (S)-(-)-nicotine, but not (S)-(-)-cotinine or (±)-trans-3′-hydroxycotinine by marmoset hepatic microsomes
    • Tsai M-C and 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 Metab Drug Interact 15:223-237.
    • (1999) Drug Metab Drug Interact , vol.15 , pp. 223-237
    • Tsai, M.-C.1    Gorrod, J.W.2
  • 35
    • 0034128936 scopus 로고    scopus 로고
    • Human UDP-glucuronosyltransferases: Metabolism, expression and disease
    • Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: Metabolism, expression and disease. Annu Rev Pharmacol Toxicol 40:581-616.
    • (2000) Annu Rev Pharmacol Toxicol , vol.40 , pp. 581-616
    • Tukey, R.H.1    Strassburg, C.P.2
  • 36
    • 0035115599 scopus 로고    scopus 로고
    • Genetic multiplicity of the human UDP-glucuronosyltransferases and regulation in the gastrointestinal tract
    • Tukey RH and Strassburg CP (2001) Genetic multiplicity of the human UDP-glucuronosyltransferases and regulation in the gastrointestinal tract. Mol Pharmacol 59:405-414.
    • (2001) Mol Pharmacol , vol.59 , pp. 405-414
    • Tukey, R.H.1    Strassburg, C.P.2
  • 37
    • 0035064372 scopus 로고    scopus 로고
    • Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk
    • Tyndale RF and Sellers EM (2001) Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk. Drug Metab Dispos 29:548-552.
    • (2001) Drug Metab Dispos , vol.29 , pp. 548-552
    • Tyndale, R.F.1    Sellers, E.M.2
  • 38
    • 0036785444 scopus 로고    scopus 로고
    • Quaternary ammonium-linked glucuronidation of I-substituted imidazoles by liver microsomes: Interspecies differences and structure-metabolism relationships
    • Vashishtha SC, Hawes EM, McCann DJ, Ghosheh O, and Hogg L (2002) Quaternary ammonium-linked glucuronidation of I-substituted imidazoles by liver microsomes: Interspecies differences and structure-metabolism relationships. Drug Metab Dispos 30:1070-1076.
    • (2002) Drug Metab Dispos , vol.30 , pp. 1070-1076
    • Vashishtha, S.C.1    Hawes, E.M.2    McCann, D.J.3    Ghosheh, O.4    Hogg, L.5


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