Mechanism-based inhibition of CYP activities in rat liver by fluoxetine and structurally similar alkylamines

References

• AVENOSO, A., SPINA, E., CAMPO, G., FACCIOLA, G., FERLITO, M., ZUCCARO, P., PERUCCA, E. and CAPUTI, A. P., 1997, Interaction between fluoxetine and haloperidol — pharmacokinetic and clinical implications. Pharmacological Research, 35, 335–339.
   PubMed Web of Science ®Google Scholar
• BAST, A. and NOORDHOEK, J., 1982, Spectral interaction of orphenadrine and its metabolites with oxidized and reduced hepatic microsomal cytochrome P-450 in the rat. Biochemical Pharmacology, 31, 2745–2753.
   PubMed Web of Science ®Google Scholar
• BAUMANN, P., 1996, Pharmacokinetic—pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clinical Pharmacokinetics, 31, 444–469.
   PubMed Web of Science ®Google Scholar
• BENSOUSSAN, C., DELAFORGE, M. and MANSUY, D., 1995, Particular ability of cytochromes CYP 3A to form inhibitory CYP—iron-metabolite complexes upon metabolic oxidation of aminodrugs. Biochemical Pharmacology, 49, 591–602.
   PubMed Web of Science ®Google Scholar
• BERGSTROM, R. F., GOLDBERG, M. J., CERIMELE, B. J. and HATCHER, B. L., 1997, Assessment of the potential for a pharmacokinetic interaction between fluoxetine and terfenadine. Clinical Pharmacology and Therapeutics, 62, 643–651.
   PubMed Web of Science ®Google Scholar
• CACCIA, S., 1998, Metabolism of the newer antidepressants — an overview of the pharmacological and pharmacokinetic implications. Clinical Pharmacokinetics, 34, 281–302.
   PubMed Web of Science ®Google Scholar
• DANIEL, W. A., HADUCH, A. and WOJCIKOWSKI, J., 2002, Inhibition and possible induction of rat CYP2D after short- and long-term treatment with antidepressants. Journal of Pharmacy and Pharmacology, 54, 1545–1552.
   PubMed Web of Science ®Google Scholar
• DELAFORGE, M., JAOUEN, M. and MANSUY, D., 1983, Dual effects of macrolide antibiotics on rat liver cytochrome P-450. Induction and formation of metabolite-complexes: a structure—activity relationship. Biochemical Pharmacology, 32, 2309–2318.
   PubMed Web of Science ®Google Scholar
• FJORDSIDE, L., JEPPESEN, U., EAP, C. B., POWELL, K., BAUMANN, P. and BROSEN, K., 1999, The stereoselective metabolism of fluoxetine in poor and extensive metabolizers of sparteine. Pharmacogenetics, 9, 55–60.
   PubMedGoogle Scholar
• FRANKLIN, M. R., 1995, Enhanced rates of cytochrome P450 metabolic-intermediate complex formation from nonmacrolide amines in rifampicin-treated rabbit liver microsomes. Drug Metabolism and Disposition, 23, 1379–1382.
   PubMed Web of Science ®Google Scholar
• HANSCH, C., LEO, A., UNGER, S. H., KIM, H. K., NIKAITANI, D. and LIEN, E. J., 1973, 'Aromatic' substituent constants for structure—activity correlations. Journal of Medicinal Chemistry, 16, 1207–1216.
   PubMed Web of Science ®Google Scholar
• HANSCH, C., ROCKWELL, S. D., Jow, P. Y. C., LEO, A. and STELLER, E. E., 1977, Substituent constants for correlation analysis. Journal of Medicinal Chemistry, 20, 304–306.
   Google Scholar
• HARVEY, A. T. and PRESKORN, S. H., 2001, Fluoxetine pharmacokinetics and effect on CYP2C19 in young and elderly volunteers. Journal of Clinical Psychopharmacology, 21, 161–166.
   PubMed Web of Science ®Google Scholar
• HEMERYCK, A., DE VRIENDT, C. and BELPAIRE, F. M., 1999, Inhibition of CYP2C9 by selective serotonin reuptake inhibitors: in vitro studies with tolbutamide and (S)-warfarin using human liver microsomes. European Journal of Clinical Pharmacology, 54, 947–951.
   PubMed Web of Science ®Google Scholar
• JEFCOATE, C. R., 1978, Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical difference spectroscopy. Methods in Enzymology, 52, 258–279.
   PubMedGoogle Scholar
• JoNssoN, K.-L. and LINDEKE, B., 1992, Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. XII. Enantioselectivity and temperature dependence in microsomes and reconstituted cytochrome P-450 systems from rat liver. Chirality, 4, 469–477.
   Google Scholar
• JONES, D. R., GORSKI, C. J. C., HAMMAN, M. A., MAYHEW, B. S., RIDER, S. and HALL, S. D., 1999, Diltiazem inhibition of cytochrome P-450 3A activity is due to metabolite intermediate complex formation. Journal of Pharmacology and Experimental Therapeutics, 290, 1116–1125.
   Google Scholar
• KOBAYASHI, K., YAMAMOTO, T., CHIBA, K., TANI, M., ISHIZAKI, T. and KUROIWA, Y., 1995, The effects of selective serotonin reuptake inhibitors and their metabolites on S-mephenytoin 4'-hydroxylase activity in human liver microsomes. British Journal of Clinical Pharmacology, 40, 481–485.
   PubMed Web of Science ®Google Scholar
• LINDEKE, B., PAULSEN, U. and ANDERSON, E., 1979, Cytochrome P-455 complex formation in the metabolism of phenylalkylamines — IV. Spectral evidences for metabolic conversion of methamphetamine to N-hydroxyamphetamine. Biochemical Pharmacology, 28, 3629–3635.
   PubMed Web of Science ®Google Scholar
• LOWRY, 0. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   Google Scholar
• MANSUY, D., ROUER, E., BACOT, C., GANS, P., CHOTTARD, J. C. and LEROUX, J. P., 1978, Interaction of aliphatic N-hydroxylamines with microsomal cytochrome P450: nature of the different derived complexes and inhibitory effects on monoxygenases activities. Biochemical Pharmacology, 27, 1229–1237.
   Google Scholar
• MARCUS, C. B., WILSON, N. M., JEFCOATE, C. R., WILKINSON, C. F. and OMIECINSKI, C. J., 1990, Selective induction of cytochrome P450 isozymes in rat liver by 4-n-alkyl-methylenedi-oxybenzenes. Archives of Biochemistry and Biophysics, 277, 8–16.
   PubMed Web of Science ®Google Scholar
• MARTINI, R., BUTLER, A. M., JIANG, X.-M. and MURRAY, M., 1995, Pretranslational down regulation of cytochrome P450 2C11 in vitamin A-deficient male rat liver: Prevention by dietary inclusion of retinoic acid. Journal of Pharmacology and Experimental Therapeutics, 273, 427–434.
   Google Scholar
• MAYHEW, B. S., JONES, D. R. and HALL, S. D., 2000, An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metabolism and Disposition, 28, 1031–1037.
   PubMed Web of Science ®Google Scholar
• MuNEIL, C. M. and MURRAY, M., 1996, Inhibition of microsomal cytochromes P450 in rat liver by the tricyclic antidepressant drug desipramine and its primary oxidized metabolites. Biochemical Pharmacology, 51, 15–20.
   Google Scholar
• MURRAY, M., 1988, Complexation of cytochrome P450 isozymes in hepatic microsomes from SKF-525-A-induced rats. Archives of Biochemistry and Biophysics, 262, 381–388.
   PubMed Web of Science ®Google Scholar
• MURRAY, M., 1992, Metabolite intermediate complexation of microsomal cytochrome CYP 2C11 in male rat liver by nortriptyline. Molecular Pharmacology, 42, 931–938.
   PubMed Web of Science ®Google Scholar
• MURRAY, M. and FIELD, S. L., 1992, Inhibition and metabolite complexation of rat hepatic microsomal cytochrome P450 by tricyclic antidepressants. Biochemical Pharmacology, 43, 2065–2071.
   PubMed Web of Science ®Google Scholar
• MURRAY, M., SEFTON, R. M., MARTINI, R. and BUTLER, A. M., 1999, Comparative induction of CYP3A and CYP2B in rat liver by 3-benzoylpyridine and meyrapone. Chemico-Biological Interactions, 113, 161–173.
   Google Scholar
• MURRAY, M., WILKINSON, C. F., MARCUS, C. and DUBE, C. E., 1983, Structure—activity relationships in the interactions of alkoxymethylenedioxybenzene derivatives with rat hepatic microsomal mixed-function oxidases in vivo. Molecular Pharmacology, 24, 129–136.
   PubMed Web of Science ®Google Scholar
• OMURA, T. and SATO, R., 1964, The carbon monoxide binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370–2378.
   PubMed Web of Science ®Google Scholar
• PERSHING, L. K. and FRANKLIN, M. R., 1982, Cytochrome P-450-metabolic-intermediate complex formation and induction by macrolide antibiotics: a new class of agents. Xenobiotica, 12, 687–699.
   PubMed Web of Science ®Google Scholar
• PESSAYRE, D., LARREY, D., VITAUX, J., BREIL, P., BELGHITI, J. and BENHAMOU, J.-P., 1982, Formation of an inactive cytochrome P-450 Fe (II)-metabolite complex after administration of troleandomycin in humans. Biochemical Pharmacology, 31, 1699–1704.
   Google Scholar
• REIDY, G. F., MEHTA, I. and MURRAY, M., 1989, Inhibition of oxidative drug metabolism by orphenadrine: in vitro and in vivo evidence for isozyme-specific complexation of cytochrome P-450 and inhibition kinetics. Molecular Pharmacology, 35, 736–743.
   PubMed Web of Science ®Google Scholar
• REIN, H., RISTAU, 0., MISSELWITZ, R., BUDER, E. and RUCKPAUL, K., 1979, The importance of the spin equilibrium in cytochrome P-450 for the reduction rate of the heme iron. Acta Biologica et Medica Germanica, 38, 187–199.
   Google Scholar
• RING, B. J., BINKLEY, S. N., RosKos, L. and WRIGHTON, S. A., 1995, Effect of fiuoxetine, norfiuoxetine, sertraline and desmethyl sertraline on human CYP3A catalyzed f-hydroxy midazolam formation in vitro. Journal of Pharmacology and Experimental Therapeutics, 275, 1131–1135.
   PubMed Web of Science ®Google Scholar
• ROOS, P. H., 1999. Common multiple interactions of tricyclic antidepressants and orphenadrine with liver microsomal cytochrome P450 enzymes of the rat. Xenobiotica, 29, 629–640.
   PubMed Web of Science ®Google Scholar
• ROOS, P. H. and MAHNKE, A., 1996, Metabolite complex formation of orphenadrine with cytochrome P450. Biochemical Pharmacology, 52, 73–84.
   PubMedGoogle Scholar
• SUTTON, D., BUTLER, A. M., NADIN, L. and MURRAY, M., 1997, Role of CYP3A4 in human hepatic diltiazem N-demethylation: Inhibition of CYP3A4 activity by oxidized diltiazem metabolites. Journal of Pharmacology and Experimental Therapeutics, 282, 294–300.
   PubMed Web of Science ®Google Scholar
• TRIEU, L. and MURRAY, M., 2000, Metabolite-intermediate complexation and inhibition of microsomal CYP3A in rat liver by diltiazem. Xenobiotica, 30, 131–140.
   PubMed Web of Science ®Google Scholar
• WAXMAN, D. J., Ko, A. and WALSH, C., 1983, Regioselectivity and stereoselectivity of androgen hydroxylations catalysed by cytochrome P-450 isozymes purified from phenobarbital-induced rat liver. Journal of Biological Chemistry, 258, 11937–11947.
   PubMed Web of Science ®Google Scholar
• YU, L.-S., WILKINSON, C. F. and ANDERS, M. W., 1980, Generation of carbon monoxide during the microsomal metabolism of methylenedioxyphenyl compounds. Biochemical Pharmacology, 29, 1113–1122.
   PubMed Web of Science ®Google Scholar