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Volumn 31, Issue 11, 2003, Pages 1352-1360

Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, A 5-lipoxygenase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

AMFEBUTAMONE; ARACHIDONATE 5 LIPOXYGENASE; BUFURALOL; CATALASE; CHLORZOXAZONE; CYTOCHROME P450 1A2; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; DICLOFENAC; DRUG DERIVATIVE; ENZYME INHIBITOR; FLUVOXAMINE; GLUTATHIONE; HYDROXYUREA; L 594615; L 754394; LIPOXYGENASE INHIBITOR; MEPHENYTOIN; PACLITAXEL; PHENACETIN; PHENAZONE; PHENYTOIN; PROPRANOLOL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE DISMUTASE; TERFENADINE; TESTOSTERONE; THEOPHYLLINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WARFARIN; ZILEUTON;

EID: 0142243111     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.31.11.1352     Document Type: Article
Times cited : (104)

References (50)
  • 1
    • 0028807678 scopus 로고
    • Pharmacokinetics and pharmacodynamics of zileuton after oral administration of single and multiple dose regimens of zileuton 600mg in healthy volunteers
    • Awni W, Braeckman RA, Granneman GR, Witt G, and Dube LM (1995a) Pharmacokinetics and pharmacodynamics of zileuton after oral administration of single and multiple dose regimens of zileuton 600mg in healthy volunteers. Clin Pharmacokinet 29 (Suppl 2):22-33.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 22-33
    • Awni, W.1    Braeckman, R.A.2    Granneman, G.R.3    Witt, G.4    Dube, L.M.5
  • 2
    • 0028828041 scopus 로고
    • The pharmacokinetic and pharmacodynamic interactions between the 5-lipoxygenase inhibitor zileuton and the cyclooxygenase inhibitor naproxen in human volunteers
    • Awni WM, Braekman RA, Cavanaugh JH, Locke CS, Linnen PJ, Granneman GR, and Dube LM (1995b) The pharmacokinetic and pharmacodynamic interactions between the 5-lipoxygenase inhibitor zileuton and the cyclooxygenase inhibitor naproxen in human volunteers. Clin Pharmacokinet 29 (Suppl 2):112-124.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 112-124
    • Awni, W.M.1    Braekman, R.A.2    Cavanaugh, J.H.3    Locke, C.S.4    Linnen, P.J.5    Granneman, G.R.6    Dube, L.M.7
  • 4
    • 0028856906 scopus 로고
    • Pharmacodynamic and stereoselective pharmacokinetic interactions between zileuton and warfarin in humans
    • Awni WM, Hussein Z, Granneman GR, Patterson KJ, Dube LM, and Cavanaugh JH (1995c) Pharmacodynamic and stereoselective pharmacokinetic interactions between zileuton and warfarin in humans. Clin Pharmacokinet 29 (Suppl 2):67-76.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 67-76
    • Awni, W.M.1    Hussein, Z.2    Granneman, G.R.3    Patterson, K.J.4    Dube, L.M.5    Cavanaugh, J.H.6
  • 8
    • 0028362263 scopus 로고
    • Characterization of the inhibition of P4501A2 by furafylline
    • Clarke SE, Ayrton AD, and Chenery RJ (1994) Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica 24:517-526.
    • (1994) Xenobiotica , vol.24 , pp. 517-526
    • Clarke, S.E.1    Ayrton, A.D.2    Chenery, R.J.3
  • 9
    • 0026356874 scopus 로고
    • Cytochrome P450 turnover
    • Correia MA (1991) Cytochrome P450 turnover. Methods Enzymol 206:315-325.
    • (1991) Methods Enzymol , vol.206 , pp. 315-325
    • Correia, M.A.1
  • 10
    • 0032800307 scopus 로고    scopus 로고
    • Zileuton, a leukotriene synthesis inhibitor in the management of chronic asthma. Clinical pharmacokinetics and safety
    • Dube LM, Swanson LJ, and Awni W (1999) Zileuton, a leukotriene synthesis inhibitor in the management of chronic asthma. Clinical pharmacokinetics and safety. Clin Rev Allergy Immunol 17:213-221.
    • (1999) Clin Rev Allergy Immunol , vol.17 , pp. 213-221
    • Dube, L.M.1    Swanson, L.J.2    Awni, W.3
  • 11
    • 0029683112 scopus 로고    scopus 로고
    • Antipyrine as a probe for human oxidative drug metabolism: Identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and norantipyrine formation
    • Engel G, Hofmann U, Heidemann H, Cosme J, and Eichelbaum M (1996) Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and norantipyrine formation. Clin Pharmacol Ther 59:613-623.
    • (1996) Clin Pharmacol Ther , vol.59 , pp. 613-623
    • Engel, G.1    Hofmann, U.2    Heidemann, H.3    Cosme, J.4    Eichelbaum, M.5
  • 13
    • 0028929645 scopus 로고
    • Metabolism of theophylline by cDNA-expressed human cytochromes P450
    • Ha HR, Chen J, Freiburghaus AU, and Follath F (i995) Metabolism of theophylline by cDNA-expressed human cytochromes P450. Br J Clin Pharmacol 39:321-326.
    • (1995) Br J Clin Pharmacol , vol.39 , pp. 321-326
    • Ha, H.R.1    Chen, J.2    Freiburghaus, A.U.3    Follath, F.4
  • 16
    • 0031723235 scopus 로고    scopus 로고
    • Prediction of pharmacokinetic alterations caused by drug-drug interactions: Metabolic interaction in the liver
    • Ito K, Iwatsubo T, Kanamitsu S, Ueda K, Suzuki H, and Sugiyama Y (1998) Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver. Pharmacol Rev 50:387-411.
    • (1998) Pharmacol Rev , vol.50 , pp. 387-411
    • Ito, K.1    Iwatsubo, T.2    Kanamitsu, S.3    Ueda, K.4    Suzuki, H.5    Sugiyama, Y.6
  • 17
    • 0033847151 scopus 로고    scopus 로고
    • CYP1A2 and CYP2D6 4-hydroxylate propranolol and both reactions exhibit racial differences
    • Johnson JA, Herring VL, Wolfe MS, and Relling MV (2000) CYP1A2 and CYP2D6 4-hydroxylate propranolol and both reactions exhibit racial differences. J Pharmacol Exp Ther 294: 1099-1105.
    • (2000) J Pharmacol Exp Ther , vol.294 , pp. 1099-1105
    • Johnson, J.A.1    Herring, V.L.2    Wolfe, M.S.3    Relling, M.V.4
  • 18
    • 85056932628 scopus 로고    scopus 로고
    • Mechanism-based inhibition of human cytochromes P450: In vitro kinetics and in vitro-in vivo correlations
    • (Rodrigues AD ed), Marcel Dekker, New York
    • Jones DR and Hall SD (2002) Mechanism-based inhibition of human cytochromes P450: in vitro kinetics and in vitro-in vivo correlations, in Drug-Drug Interactions (Rodrigues AD ed) pp 387-413, Marcel Dekker, New York.
    • (2002) Drug-Drug Interactions , pp. 387-413
    • Jones, D.R.1    Hall, S.D.2
  • 19
    • 0031015345 scopus 로고    scopus 로고
    • Human P450 metabolism of warfarin
    • Kaminsky LS and Zhang ZY (1996) Human P450 metabolism of warfarin. Pharmacol Ther 73:67-74.
    • (1996) Pharmacol Ther , vol.73 , pp. 67-74
    • Kaminsky, L.S.1    Zhang, Z.Y.2
  • 21
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • Kunze K and Trager WF (1993) Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem Res Toxicol 6:649-656.
    • (1993) Chem Res Toxicol , vol.6 , pp. 649-656
    • Kunze, K.1    Trager, W.F.2
  • 22
    • 0025865462 scopus 로고
    • Inhibition of theophylline metabolism by mexiletine in young male and female nonsmokers
    • Lo CM, We XX, and Vestal RE (1991) Inhibition of theophylline metabolism by mexiletine in young male and female nonsmokers. Clin Pharmacol Ther 49:571-580.
    • (1991) Clin Pharmacol Ther , vol.49 , pp. 571-580
    • Lo, C.M.1    We, X.X.2    Vestal, R.E.3
  • 23
    • 0028078626 scopus 로고
    • Thiophene derivatives as new mechanism-based inhibitors of cytochromes P450: Inactivation of yeast-expressed human liver cytochrome P450 2C9 by tienilic acid
    • Lopez-Garcia MP, Danselle PM, and Mansuy D (1994) Thiophene derivatives as new mechanism-based inhibitors of cytochromes P450: inactivation of yeast-expressed human liver cytochrome P450 2C9 by tienilic acid. Biochemistry 33:166-175.
    • (1994) Biochemistry , vol.33 , pp. 166-175
    • Lopez-Garcia, M.P.1    Danselle, P.M.2    Mansuy, D.3
  • 24
    • 0028791821 scopus 로고
    • In vitro plasma protein binding of zileuton and its N-dehydroxylated metabolite
    • Machinist JM, Kukulka MJ, and Bopp BA (1995a) In vitro plasma protein binding of zileuton and its N-dehydroxylated metabolite. Clin Pharmacokinet 29 (Suppl 2):34-41.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 34-41
    • Machinist, J.M.1    Kukulka, M.J.2    Bopp, B.A.3
  • 25
    • 0031724342 scopus 로고    scopus 로고
    • Identification of the human liver cytochrome P450 enzymes involved in the in vitro metabolism of a novel 5-lipoxygenase inhibitor
    • Machinist JM, Mayer MD, Roberts EM, Surber BW, and Rodrigues AD (1998) Identification of the human liver cytochrome P450 enzymes involved in the in vitro metabolism of a novel 5-lipoxygenase inhibitor. Drug Metab Dispos 26:970-976.
    • (1998) Drug Metab Dispos , vol.26 , pp. 970-976
    • Machinist, J.M.1    Mayer, M.D.2    Roberts, E.M.3    Surber, B.W.4    Rodrigues, A.D.5
  • 26
    • 0028785979 scopus 로고
    • Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193
    • Machinist JM, Mayer MD, Shet MS, Ferrero JL, and Rodrigues AD (1995b) Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos 23:1163-1174.
    • (1995) Drug Metab Dispos , vol.23 , pp. 1163-1174
    • Machinist, J.M.1    Mayer, M.D.2    Shet, M.S.3    Ferrero, J.L.4    Rodrigues, A.D.5
  • 27
    • 0013212389 scopus 로고    scopus 로고
    • In vitro approaches for studying the inhibition of drug-metabolizing enzymes and identifying the drug-metabolizing enzymes responsible for the metabolism of drugs
    • (Rodrigues AD ed), Marcel Dekker, New York
    • Madan A, Usuki E, Burton LA, Ogilvie BW, and Parkinson A (2002) In vitro approaches for studying the inhibition of drug-metabolizing enzymes and identifying the drug-metabolizing enzymes responsible for the metabolism of drugs. in Drug-Drug Interactions (Rodrigues AD ed) pp 217-294, Marcel Dekker, New York.
    • (2002) Drug-Drug Interactions , pp. 217-294
    • Madan, A.1    Usuki, E.2    Burton, L.A.3    Ogilvie, B.W.4    Parkinson, A.5
  • 28
    • 0000167768 scopus 로고
    • Thiophene S-oxides as new reactive metabolites: Formation by cytochrome P450 dependent oxidation and reaction with nucleophiles
    • Mansuy D, Valadon P, Erdelmeier I, Lopez-Garcia P, Amar C, Girault JP, and Dansette PM (1991) Thiophene S-oxides as new reactive metabolites: formation by cytochrome P450 dependent oxidation and reaction with nucleophiles. J. Am Chem Soc 113:7825-2826.
    • (1991) J Am Chem Soc , vol.113 , pp. 7825-2826
    • Mansuy, D.1    Valadon, P.2    Erdelmeier, I.3    Lopez-Garcia, P.4    Amar, C.5    Girault, J.P.6    Dansette, P.M.7
  • 30
    • 0033831197 scopus 로고    scopus 로고
    • An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation
    • Mayhew BS, Jones DR, and Hall SD (2000) An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos 28:1031-1037.
    • (2000) Drug Metab Dispos , vol.28 , pp. 1031-1037
    • Mayhew, B.S.1    Jones, D.R.2    Hall, S.D.3
  • 31
    • 0031431835 scopus 로고    scopus 로고
    • Griseofulvin and fluvoxamine interactions with the metabolism of theophylline
    • Rasmussen BB, Jeppesen U, Gaist D, and Brosen K (1997) Griseofulvin and fluvoxamine interactions with the metabolism of theophylline. Ther Drug Monit 19:56-62.
    • (1997) Ther Drug Monit , vol.19 , pp. 56-62
    • Rasmussen, B.B.1    Jeppesen, U.2    Gaist, D.3    Brosen, K.4
  • 32
    • 0028898044 scopus 로고
    • Selective serotonin reuptake inhibitors and theophylline metabolism in human liver microsomes: Potent inhibition by fluvoxamine
    • Rasmussen BB, Maenpaa J, Pelkonen O, Loft S, Poulsen HE, Lykkesfeldt J, and Brosen K (1995) Selective serotonin reuptake inhibitors and theophylline metabolism in human liver microsomes: potent inhibition by fluvoxamine. Br J Clin Pharmacol 39:151-159.
    • (1995) Br J Clin Pharmacol , vol.39 , pp. 151-159
    • Rasmussen, B.B.1    Maenpaa, J.2    Pelkonen, O.3    Loft, S.4    Poulsen, H.E.5    Lykkesfeldt, J.6    Brosen, K.7
  • 34
    • 0028802939 scopus 로고
    • Lack of pharmacokinetic interaction between zileuton and phenytoin in humans
    • Samara E, Cavanaugh JH, Mukherjee D, and Granneman GR (1995) Lack of pharmacokinetic interaction between zileuton and phenytoin in humans. Clin Pharmacokinet 29 (Suppl 2):84-91.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 84-91
    • Samara, E.1    Cavanaugh, J.H.2    Mukherjee, D.3    Granneman, G.R.4
  • 35
    • 0036914221 scopus 로고    scopus 로고
    • Influence of CYP2C9 and CYP2C19 genetic polymorphisms on warfarin maintenance dose and metabolic clearance
    • Scordo MG, Pengo V, Spina E, Dahl ML, Gusella M, and Padrini R (2002) Influence of CYP2C9 and CYP2C19 genetic polymorphisms on warfarin maintenance dose and metabolic clearance. Clin Pharmacol Ther 72:702-710.
    • (2002) Clin Pharmacol Ther , vol.72 , pp. 702-710
    • Scordo, M.G.1    Pengo, V.2    Spina, E.3    Dahl, M.L.4    Gusella, M.5    Padrini, R.6
  • 36
    • 0029875703 scopus 로고    scopus 로고
    • Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine
    • Sharer JE and Wrighton SA (1996) Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos 24:487-494.
    • (1996) Drug Metab Dispos , vol.24 , pp. 487-494
    • Sharer, J.E.1    Wrighton, S.A.2
  • 39
    • 0028896856 scopus 로고
    • Stereoselective glucuronidation of zileuton isomers by human hepatic microsomes
    • Sweeny DJ and Nellans HN (1995) Stereoselective glucuronidation of zileuton isomers by human hepatic microsomes. Drug Metab Dispos 23:149-153.
    • (1995) Drug Metab Dispos , vol.23 , pp. 149-153
    • Sweeny, D.J.1    Nellans, H.N.2
  • 42
    • 0030094638 scopus 로고    scopus 로고
    • Theophylline metabolism in human liver microsomes: Inhibition studies
    • Tjia JF, Colbert J, and Back DJ (1996) Theophylline metabolism in human liver microsomes: inhibition studies. J Pharmacol Exp Ther 276:912-917.
    • (1996) J Pharmacol Exp Ther , vol.276 , pp. 912-917
    • Tjia, J.F.1    Colbert, J.2    Back, D.J.3
  • 43
    • 0028927771 scopus 로고
    • Influence of endogenous and exogenous effectors on the pharmaeokinetics of theophylline
    • Troger U and Meyer FP (1995) Influence of endogenous and exogenous effectors on the pharmaeokinetics of theophylline. Clin Pharmacokinet 28:287-314.
    • (1995) Clin Pharmacokinet , vol.28 , pp. 287-314
    • Troger, U.1    Meyer, F.P.2
  • 44
    • 0021917028 scopus 로고
    • Quantitative account of propranolol metabolism in urine of normal man
    • Walle T, Walle UK, and Olanoff LS (1985) Quantitative account of propranolol metabolism in urine of normal man. Drug Metab Dispos 13:204-209.
    • (1985) Drug Metab Dispos , vol.13 , pp. 204-209
    • Walle, T.1    Walle, U.K.2    Olanoff, L.S.3
  • 45
    • 0030035655 scopus 로고    scopus 로고
    • Zileuton: The first 5-lipoxygenase inhibitor for the treatment of asthma
    • Wenzel SE and Kamada AK (1996) Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother 30:858-864.
    • (1996) Ann Pharmacother , vol.30 , pp. 858-864
    • Wenzel, S.E.1    Kamada, A.K.2
  • 46
    • 0028805995 scopus 로고
    • The pharmacokinetics of single oral doses of zileuton 200 to 800 mg, its enantiomers and its metabolites, in normal healthy volunteers
    • Wong SL, Awni WM, Cavanaugh JH, El-Shourbagy T, Locke CS, and Dube LM (1995) The pharmacokinetics of single oral doses of zileuton 200 to 800 mg, its enantiomers and its metabolites, in normal healthy volunteers. Clin Pharmacokinet 29 (Suppl 2):9-21.
    • (1995) Clin Pharmacokinet , vol.29 , Issue.SUPPL. 2 , pp. 9-21
    • Wong, S.L.1    Awni, W.M.2    Cavanaugh, J.H.3    El-Shourbagy, T.4    Locke, C.S.5    Dube, L.M.6
  • 47
    • 0031680048 scopus 로고    scopus 로고
    • Lack of cytochrome P450 1A2 interaction effect of ABT-761 on the pharmacokinetics of theophylline
    • Wong SL, Cavanaugh JH, Qian J, Hansen R, and Awni WM (1998) Lack of cytochrome P450 1A2 interaction effect of ABT-761 on the pharmacokinetics of theophylline. Am J Ther 5:303-306.
    • (1998) Am J Ther , vol.5 , pp. 303-306
    • Wong, S.L.1    Cavanaugh, J.H.2    Qian, J.3    Hansen, R.4    Awni, W.M.5
  • 48
    • 0035215519 scopus 로고    scopus 로고
    • Fluvoxamine-theophylline interaction: Gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2
    • Yao C, Kunze KL, Kharasch ED, Wang Y, Trager WF, Ragueneau I, and Levy RH (2001) Fluvoxamine-theophylline interaction: gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2. Clin Pharmacol Ther 70:415-424.
    • (2001) Clin Pharmacol Ther , vol.70 , pp. 415-424
    • Yao, C.1    Kunze, K.L.2    Kharasch, E.D.3    Wang, Y.4    Trager, W.F.5    Ragueneau, I.6    Levy, R.H.7
  • 49
    • 0028956887 scopus 로고
    • Identification of the human CYP isoforms involved in the metabolism of propranolol enantiomers: N-desisopropylation is mediated mainly by CYP1A2
    • Yoshimoto K, Echizen H, Chiba K, Tani M, and Ishizaki T (1995) Identification of the human CYP isoforms involved in the metabolism of propranolol enantiomers: N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol 39:421-431.
    • (1995) Br J Clin Pharmacol , vol.39 , pp. 421-431
    • Yoshimoto, K.1    Echizen, H.2    Chiba, K.3    Tani, M.4    Ishizaki, T.5
  • 50
    • 0029018483 scopus 로고
    • Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation
    • Zhang ZY and Kaminsky LS (1995) Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation. Biochem Pharmacol 50:205-211.
    • (1995) Biochem Pharmacol , vol.50 , pp. 205-211
    • Zhang, Z.Y.1    Kaminsky, L.S.2


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