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Volumn 18, Issue 3, 1997, Pages 227-240

Metabolism of dextromethorphan in vitro: Involvement of cytochromes P450 2D6 and 3A3/4, with a possible role of 2E1

Author keywords

3 methoxymorphinan; cytochrome P450; dextromethorphan; dextrorphan; human liver microsomes; in vitro

Indexed keywords

ALPHA NAPHTHOFLAVONE; CYTOCHROME P450; DEXTROMETHORPHAN; DRUG METABOLITE; QUINIDINE; SULFAPHENAZOLE;

EID: 0030889604     PISSN: 01422782     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-081X(199704)18:3<227::AID-BDD18>3.0.CO;2-L     Document Type: Article
Times cited : (92)

References (45)
  • 1
    • 0018975120 scopus 로고
    • The urinary excretion of dextromethorphan and three metabolites in dogs and humans
    • J. W. Beinhart, The urinary excretion of dextromethorphan and three metabolites in dogs and humans. Toxicol. Appl. Pharmacol., 55, 43-48 (1980).
    • (1980) Toxicol. Appl. Pharmacol. , vol.55 , pp. 43-48
    • Beinhart, J.W.1
  • 2
    • 0020583467 scopus 로고
    • Inter-individual variation in the metabolism of dextromethorphan
    • G. Pfaff, P. Briegel and I. Lamprecht, Inter-individual variation in the metabolism of dextromethorphan. Int. J. Clin. Pharmacol., 14, 173-189 (1983).
    • (1983) Int. J. Clin. Pharmacol. , vol.14 , pp. 173-189
    • Pfaff, G.1    Briegel, P.2    Lamprecht, I.3
  • 4
    • 0022338958 scopus 로고
    • Polymorphic dextromethorphan metabolism: Co-segregation of oxidative O-demethylation with debrisoquine hydroxylation
    • B. Schmid, J. Bircher, R. Preisig and A. Küpfer, Polymorphic dextromethorphan metabolism: co-segregation of oxidative O-demethylation with debrisoquine hydroxylation. Clin. Pharmacol. Ther., 38, 618-624 (1985).
    • (1985) Clin. Pharmacol. Ther. , vol.38 , pp. 618-624
    • Schmid, B.1    Bircher, J.2    Preisig, R.3    Küpfer, A.4
  • 5
    • 0022501297 scopus 로고
    • Pharmacogenetics of dextromethorphan O-demethylation in man
    • A. Küpfer, B. Schmid and G. Pfaff, Pharmacogenetics of dextromethorphan O-demethylation in man. Xenobiotica, 16, 421-433 (1986).
    • (1986) Xenobiotica , vol.16 , pp. 421-433
    • Küpfer, A.1    Schmid, B.2    Pfaff, G.3
  • 6
    • 0024535619 scopus 로고
    • Dextromethorphan: Polymorphic serum pattern of the O-demethylated and didemethylated metabolites in man
    • O. Mortimer, B. Lindstrom, H. Laurell, U. Bergman and A. Rane, Dextromethorphan: polymorphic serum pattern of the O-demethylated and didemethylated metabolites in man. Br. J. Clin. Pharmacol., 27, 223-227 (1989).
    • (1989) Br. J. Clin. Pharmacol. , vol.27 , pp. 223-227
    • Mortimer, O.1    Lindstrom, B.2    Laurell, H.3    Bergman, U.4    Rane, A.5
  • 7
    • 0023884310 scopus 로고
    • Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydroxylation (cytochrome P-450 dbl/bufI)
    • P. Dayer, J. Desmeules, T. Leemann and R. Striberni, Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydroxylation (cytochrome P-450 dbl/bufI). Biochem. Biophys. Res. Commun., 152, 411-416 (1988).
    • (1988) Biochem. Biophys. Res. Commun. , vol.152 , pp. 411-416
    • Dayer, P.1    Desmeules, J.2    Leemann, T.3    Striberni, R.4
  • 8
    • 0025103215 scopus 로고
    • Polymorphic formation of morphine from codeine in poor and extensive metabolizers of dextromethorphan. Relationship to the presence of immunoidentified cytochrome P-450 IID1
    • O. Mortimer, K. Persson, M. G. Ladona, D. Spalding, U. M. Zanger, U. Mayer and A. Rane, Polymorphic formation of morphine from codeine in poor and extensive metabolizers of dextromethorphan. Relationship to the presence of immunoidentified cytochrome P-450 IID1. Clin. Pharmacol. Ther., 47, 27-35 (1990).
    • (1990) Clin. Pharmacol. Ther. , vol.47 , pp. 27-35
    • Mortimer, O.1    Persson, K.2    Ladona, M.G.3    Spalding, D.4    Zanger, U.M.5    Mayer, U.6    Rane, A.7
  • 11
    • 0023823667 scopus 로고
    • Simplified phenotyping with dextromethorphan by thin-layer chromatography: Application to clinical laboratory screening for deficiencies in oxidative drug metabolism
    • R. J. Guttendorf, P. J. Wedlund, J. Blake and S. L. Chang, Simplified phenotyping with dextromethorphan by thin-layer chromatography: application to clinical laboratory screening for deficiencies in oxidative drug metabolism. Ther. Drug Monit., 10, 490-498 (1988).
    • (1988) Ther. Drug Monit. , vol.10 , pp. 490-498
    • Guttendorf, R.J.1    Wedlund, P.J.2    Blake, J.3    Chang, S.L.4
  • 12
    • 0027265750 scopus 로고
    • CYP2D6- and CYP3A-dependent metabolism of dextromethorphan in humans
    • E. Jacqz-Aigrain, C. Funck-Brentano and T. Cresteil, CYP2D6-and CYP3A-dependent metabolism of dextromethorphan in humans. Pharmacogenetics, 3, 197-204 (1993).
    • (1993) Pharmacogenetics , vol.3 , pp. 197-204
    • Jacqz-Aigrain, E.1    Funck-Brentano, C.2    Cresteil, T.3
  • 16
    • 0027264432 scopus 로고
    • Cytochrome P450TB (CYP2C): A major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver
    • T. Leemann, C. Transon and P. Dayer, Cytochrome P450TB (CYP2C): a major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver. Life Sci., 52, 29-34 (1993).
    • (1993) Life Sci. , vol.52 , pp. 29-34
    • Leemann, T.1    Transon, C.2    Dayer, P.3
  • 17
    • 0028038065 scopus 로고
    • The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: In vitro studies using human liver microsomes
    • N. L. Kerry, A. A. Somogyi, F. Bochner and G. Mikus, The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: in vitro studies using human liver microsomes. Br. J. Clin. Pharmacol., 38, 243-248 (1994).
    • (1994) Br. J. Clin. Pharmacol. , vol.38 , pp. 243-248
    • Kerry, N.L.1    Somogyi, A.A.2    Bochner, F.3    Mikus, G.4
  • 18
    • 0027956791 scopus 로고
    • Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily
    • J. C. Gorski, D. R. Jones, S. A. Wrighton and S. D. Hall, Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily. Biochem. Pharmacol., 48, 173-182 (1994).
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 173-182
    • Gorski, J.C.1    Jones, D.R.2    Wrighton, S.A.3    Hall, S.D.4
  • 19
    • 0029979348 scopus 로고    scopus 로고
    • Inhibition of cytochrome P450 by nefazodone in vitro: Studies of dextromethorphan O- and N-demethylation
    • J. Schmider, D. J. Greenblatt, L. L. von Moltke, J. S. Harmatz and R. I. Shader, Inhibition of cytochrome P450 by nefazodone in vitro: studies of dextromethorphan O-and N-demethylation. Br. J. Clin. Pharmacol., 41, 339-343 (1996).
    • (1996) Br. J. Clin. Pharmacol. , vol.41 , pp. 339-343
    • Schmider, J.1    Greenblatt, D.J.2    Von Moltke, L.L.3    Harmatz, J.S.4    Shader, R.I.5
  • 21
    • 0028828577 scopus 로고
    • Coadministration of nefazodone and benzodiazepines: II. Pharmacokinetic interaction study with triazolam
    • R. H. Barbhaiya, U. A. Shukla, P. D. Kroboth and D. S. Greene, Coadministration of nefazodone and benzodiazepines: II. Pharmacokinetic interaction study with triazolam. J. Clin. Psychopharmacol., 15, 320-326 (1995).
    • (1995) J. Clin. Psychopharmacol. , vol.15 , pp. 320-326
    • Barbhaiya, R.H.1    Shukla, U.A.2    Kroboth, P.D.3    Greene, D.S.4
  • 22
    • 0029584313 scopus 로고
    • Coadministration of nefazodone and benzodiazepines: III. Pharmacokinetic interaction study with alprazolam
    • D. S. Greene, D. E. Salazar, R. C. Dockens, P. Kroboth and R. H. Barbhaiya, Coadministration of nefazodone and benzodiazepines: III. Pharmacokinetic interaction study with alprazolam. J. Clin. Psychopharmacol., 15, 399-408 (1995).
    • (1995) J. Clin. Psychopharmacol. , vol.15 , pp. 399-408
    • Greene, D.S.1    Salazar, D.E.2    Dockens, R.C.3    Kroboth, P.4    Barbhaiya, R.H.5
  • 23
    • 0029558898 scopus 로고
    • N-demethylation of amitriptyline in vitro: Role of cytochrome P-450 3A (CYP3A) isoforms and effect of metabolic inhibitors
    • J. Schmider, D. J. Greenblatt, L. L. von Moltke, J. S. Harmatz and R. I. Shader, N-demethylation of amitriptyline in vitro: role of cytochrome P-450 3A (CYP3A) isoforms and effect of metabolic inhibitors. J. Pharmacol. Exp. Ther., 275, 592-597 (1995).
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 592-597
    • Schmider, J.1    Greenblatt, D.J.2    Von Moltke, L.L.3    Harmatz, J.S.4    Shader, R.I.5
  • 24
    • 0027326229 scopus 로고
    • Alprazolam metabolism in vitro: Studies of human, monkey, mouse, and rat liver microsomes
    • L. L. von Moltke, D. J. Greenblatt, J. S. Harmatz and R. I. Shader, Alprazolam metabolism in vitro: studies of human, monkey, mouse, and rat liver microsomes. Pharmacology, 47, 268-276 (1993).
    • (1993) Pharmacology , vol.47 , pp. 268-276
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Harmatz, J.S.3    Shader, R.I.4
  • 25
    • 0028194864 scopus 로고
    • Inhibition of desipramine hydroxylation in vitro by serotonin-reuptake-inhibitor antidepressants, and by quinidine and ketoconazole: A model system to predict drug interactions in vivo
    • L. L. von Moltke, D. J. Greenblatt, M. M. Cotreau-Bibbo, S. X. Duan, J. S. Harmatz and R. I. Shader, Inhibition of desipramine hydroxylation in vitro by serotonin-reuptake-inhibitor antidepressants, and by quinidine and ketoconazole: a model system to predict drug interactions in vivo. J. Pharmacol. Exp. Ther., 268, 1278-1283 (1994).
    • (1994) J. Pharmacol. Exp. Ther. , vol.268 , pp. 1278-1283
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Cotreau-Bibbo, M.M.3    Duan, S.X.4    Harmatz, J.S.5    Shader, R.I.6
  • 26
    • 0028279667 scopus 로고
    • Inhibitors of alprazolam metabolism in vitro: Effect of serotonin-reuptake-inhibitor antidepressants, ketoconazole and quinidine
    • L. L. von Moltke, D. J. Greenblatt, M. M. Cotreau-Bibbo, J. S. Harmatz and R. I. Shader, Inhibitors of alprazolam metabolism in vitro: effect of serotonin-reuptake-inhibitor antidepressants, ketoconazole and quinidine. Br. J. Clin. Pharmacol., 38, 23-31 (1994).
    • (1994) Br. J. Clin. Pharmacol. , vol.38 , pp. 23-31
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Cotreau-Bibbo, M.M.3    Harmatz, J.S.4    Shader, R.I.5
  • 28
    • 0030041594 scopus 로고    scopus 로고
    • Characterization of six in vitro reactions mediated by human cytochrome P450: Application to the testing of cytochrome P450-directed antibodies
    • J. Schmider, D. J. Greenblatt, L. L. von Moltke, J. S. Harmatz, S. X. Duan, D. Karsov and R. I. Shader, Characterization of six in vitro reactions mediated by human cytochrome P450: application to the testing of cytochrome P450-directed antibodies. Pharmacology, 52, 125-134 (1996).
    • (1996) Pharmacology , vol.52 , pp. 125-134
    • Schmider, J.1    Greenblatt, D.J.2    Von Moltke, L.L.3    Harmatz, J.S.4    Duan, S.X.5    Karsov, D.6    Shader, R.I.7
  • 30
    • 0028858960 scopus 로고
    • Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • D. J. Newton, R. W. Wang and A. Y. H. Lu, Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab. Disposit., 23, 154-158 (1995).
    • (1995) Drug Metab. Disposit , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.H.3
  • 32
    • 0028898816 scopus 로고
    • Inhibition of alprazolam and desipramine hydroxylation in vitro by paroxetine and fluvoxamine: Comparison with other selective serotonin-reuptake-inhibitor antidepressants
    • L. L. von Moltke, D. J. Greenblatt, M. H. Court, S. X. Duan, J. S. Harmatz and R. I. Shader, Inhibition of alprazolam and desipramine hydroxylation in vitro by paroxetine and fluvoxamine: comparison with other selective serotonin-reuptake-inhibitor antidepressants. J. Clin. Psychopharmacol., 15, 125-131 (1995).
    • (1995) J. Clin. Psychopharmacol. , vol.15 , pp. 125-131
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Court, M.H.3    Duan, S.X.4    Harmatz, J.S.5    Shader, R.I.6
  • 33
    • 0029934305 scopus 로고    scopus 로고
    • Enzyme kinetic modeling as a tool to analyse the behaviour of cytochrome P450 catalysed reactions: Application to amitriptyline N-demethylation
    • J. Schmider, D. J. Greenblatt, J. S. Harmatz and R. I. Shader, Enzyme kinetic modeling as a tool to analyse the behaviour of cytochrome P450 catalysed reactions: application to amitriptyline N-demethylation. Br. J. Clin. Pharmacol., 41, 593-604 (1996).
    • (1996) Br. J. Clin. Pharmacol. , vol.41 , pp. 593-604
    • Schmider, J.1    Greenblatt, D.J.2    Harmatz, J.S.3    Shader, R.I.4
  • 34
    • 0023949862 scopus 로고
    • Modulation of rabbit and human hepatic cytochrome P-450-catalyzed steroid hydroxylations by alpha-naphthoflavone
    • G. E. Schwab, J. L. Raucy and E. F. Johnson, Modulation of rabbit and human hepatic cytochrome P-450-catalyzed steroid hydroxylations by alpha-naphthoflavone. Mol. Pharmacol., 33, 493-499 (1988).
    • (1988) Mol. Pharmacol. , vol.33 , pp. 493-499
    • Schwab, G.E.1    Raucy, J.L.2    Johnson, E.F.3
  • 35
    • 0027935778 scopus 로고
    • Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms
    • T. Andersson, J. O. Miners, M. E. Veronese and D. J. Birkett, Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. Br. J. Clin. Pharmacol., 38, 131-137 (1994).
    • (1994) Br. J. Clin. Pharmacol. , vol.38 , pp. 131-137
    • Andersson, T.1    Miners, J.O.2    Veronese, M.E.3    Birkett, D.J.4
  • 36
    • 0028307539 scopus 로고
    • Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site
    • M. Shou, J. Grogan, J. A. Mancewicz, K. W. Krausz, F. J. Gonzalez, H. V. Gelboin and K. R. Korzekwa, Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry, 33, 6450-6455 (1994).
    • (1994) Biochemistry , vol.33 , pp. 6450-6455
    • Shou, M.1    Grogan, J.2    Mancewicz, J.A.3    Krausz, K.W.4    Gonzalez, F.J.5    Gelboin, H.V.6    Korzekwa, K.R.7
  • 37
    • 0028174881 scopus 로고
    • Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450
    • T. K. Chang, F. J. Gonzalez and D. J. Waxman, Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch. Biochem. Biophys., 311, 437-442 (1994)
    • (1994) Arch. Biochem. Biophys. , vol.311 , pp. 437-442
    • Chang, T.K.1    Gonzalez, F.J.2    Waxman, D.J.3
  • 38
    • 0028151666 scopus 로고
    • Lauric acid as a model substrate for the simultaneous determination of cytochrome P450 2E1 and 4a in hepatic microsomes
    • S. E. Clarke, S. J. Baldwin, J. C. Bloomer, A. D. Ayrton, R. S. Sozio and R. J. Chenery, Lauric acid as a model substrate for the simultaneous determination of cytochrome P450 2E1 and 4A in hepatic microsomes. Chem. Res. Toxicol., 7, 836-842 (1994).
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 836-842
    • Clarke, S.E.1    Baldwin, S.J.2    Bloomer, J.C.3    Ayrton, A.D.4    Sozio, R.S.5    Chenery, R.J.6
  • 39
    • 0027487006 scopus 로고
    • Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques
    • W. Tassaneeyakul, M. E. Veronese, D. J. Birkett, F. J. Gonzalez and J. O. Miners, Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol., 46, 1975-1981 (1993).
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1975-1981
    • Tassaneeyakul, W.1    Veronese, M.E.2    Birkett, D.J.3    Gonzalez, F.J.4    Miners, J.O.5
  • 40
    • 0027515708 scopus 로고
    • Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane
    • E. D. Kharasch and K. E. Thummel, Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Anesthesiology, 79, 795-807 (1993).
    • (1993) Anesthesiology , vol.79 , pp. 795-807
    • Kharasch, E.D.1    Thummel, K.E.2
  • 41
    • 0027949221 scopus 로고
    • Dextromethorphan inhibits ischemia-induced c-fos expression and delayed neuronal death in hippocampal neurons
    • P. M. Bokesch, J. E. Marchand, C. S. Connelly, W. H. Wurm and R. M. Kream, Dextromethorphan inhibits ischemia-induced c-fos expression and delayed neuronal death in hippocampal neurons. Anesthesiology, 81, 470-477 (1994).
    • (1994) Anesthesiology , vol.81 , pp. 470-477
    • Bokesch, P.M.1    Marchand, J.E.2    Connelly, C.S.3    Wurm, W.H.4    Kream, R.M.5
  • 42
    • 0028040424 scopus 로고
    • Dextromethorphan: Cellular effects reducing neuronal hyperactivity
    • G. Trube and R. Netzer, Dextromethorphan: cellular effects reducing neuronal hyperactivity. Epilepsia, 35, S62-S67 (1994).
    • (1994) Epilepsia , vol.35
    • Trube, G.1    Netzer, R.2
  • 43
    • 0027302752 scopus 로고
    • Differences in anticonvulsant potency and adverse effects between dextromethorphan and dextrorphan in amygdala-kindled and non-kindled rats
    • W. Löscher and D. Honack, Differences in anticonvulsant potency and adverse effects between dextromethorphan and dextrorphan in amygdala-kindled and non-kindled rats. Eur. J. Pharmacol., 238, 191-200 (1993).
    • (1993) Eur. J. Pharmacol. , vol.238 , pp. 191-200
    • Löscher, W.1    Honack, D.2
  • 44
    • 0023941322 scopus 로고
    • Anticonvulsant effects of dextrorphan in rats: Possible involvement in dextromethorphan-induced seizure protection
    • F. C. Tortella, J. W. Ferkany and M. J. Pontecorvo, Anticonvulsant effects of dextrorphan in rats: possible involvement in dextromethorphan-induced seizure protection. Life Sci., 42, 2509-2514 (1988).
    • (1988) Life Sci. , vol.42 , pp. 2509-2514
    • Tortella, F.C.1    Ferkany, J.W.2    Pontecorvo, M.J.3
  • 45
    • 0025050694 scopus 로고
    • Antiepileptic drugs: Pharmacological mechanisms and clincal efficacy with consideration of promising developmental stage compounds
    • M. A. Rogawski and R. J. Porter, Antiepileptic drugs: pharmacological mechanisms and clincal efficacy with consideration of promising developmental stage compounds. Pharmacol. Rev., 42, 223-286 (1990).
    • (1990) Pharmacol. Rev. , vol.42 , pp. 223-286
    • Rogawski, M.A.1    Porter, R.J.2


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