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Volumn 77, Issue 3, 2009, Pages 444-450

Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N-(1-phenyl cyclohexyl)-2-ethoxyethanamine and N-(1-phenylcyclohexyl)-2-methoxyethanamine

Author keywords

Cytochrome P450; Designer drugs; HLM; N (1 Phenylcyclohexyl) 2 ethoxyethanamine; N (1 Phenylcyclohexyl) 2 methoxyethanamine

Indexed keywords

4 (4 CHLOROBENZYL)PYRIDINE; CYTOCHROME P450; CYTOCHROME P450 2B6; CYTOCHROME P450 2C9; CYTOCHROME P450 3A4; CYTOCHROME P450 INHIBITOR; DESIGNER DRUG; KETOCONAZOLE; N (1 PHENYLCYCLOHEXYL) 2 METHOXYETHANAMINE; N (1PHENYLCYCLOHEXYL) 2 ETHOXYETHANAMINE; SULFAPHENAZOLE; UNCLASSIFIED DRUG;

EID: 58249130589     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.10.024     Document Type: Article
Times cited : (14)

References (32)
  • 1
    • 84892246340 scopus 로고    scopus 로고
    • Human cytochrome P450 enzymes
    • Ortiz-de-Montellano P.R. (Ed), Kluwer Academic/Plenum Publishers, New York
    • Guengerich F.P. Human cytochrome P450 enzymes. In: Ortiz-de-Montellano P.R. (Ed). Cytochrome P450-structure, mechanism, and biochemistry. 3rd ed. (2005), Kluwer Academic/Plenum Publishers, New York 377-530
    • (2005) Cytochrome P450-structure, mechanism, and biochemistry. 3rd ed. , pp. 377-530
    • Guengerich, F.P.1
  • 2
    • 0028178550 scopus 로고
    • The demethylenation of methylenedioxymethamphetamine ("ecstasy") by debrisoquine hydroxylase (CYP2D6)
    • Tucker G.T., Lennard M.S., Ellis S.W., Woods H.F., Cho A.K., Lin L.Y., et al. The demethylenation of methylenedioxymethamphetamine ("ecstasy") by debrisoquine hydroxylase (CYP2D6). Biochem Pharmacol 47 (1994) 1151-1156
    • (1994) Biochem Pharmacol , vol.47 , pp. 1151-1156
    • Tucker, G.T.1    Lennard, M.S.2    Ellis, S.W.3    Woods, H.F.4    Cho, A.K.5    Lin, L.Y.6
  • 3
    • 0343145695 scopus 로고    scopus 로고
    • Interactions of amphetamine analogs with human liver CYP2D6
    • Wu D., Otton S.V., Inaba T., Kalow W., and Sellers E.M. Interactions of amphetamine analogs with human liver CYP2D6. Biochem Pharmacol 53 (1997) 1605-1612
    • (1997) Biochem Pharmacol , vol.53 , pp. 1605-1612
    • Wu, D.1    Otton, S.V.2    Inaba, T.3    Kalow, W.4    Sellers, E.M.5
  • 5
    • 0000174201 scopus 로고
    • Synthesis of phencyclidine and other 1-arylcyclohexylamines
    • Maddox V.H., Godefroi E.F., and Parcell R.F. Synthesis of phencyclidine and other 1-arylcyclohexylamines. J Med Chem 8 (1965) 230-235
    • (1965) J Med Chem , vol.8 , pp. 230-235
    • Maddox, V.H.1    Godefroi, E.F.2    Parcell, R.F.3
  • 7
    • 40649107645 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry
    • Sauer C., Peters F.T., Staack R.F., Fritschi G., and Maurer H.H. Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry. J Chromatogr A 1186 (2008) 380-390
    • (2008) J Chromatogr A , vol.1186 , pp. 380-390
    • Sauer, C.1    Peters, F.T.2    Staack, R.F.3    Fritschi, G.4    Maurer, H.H.5
  • 8
    • 33748345156 scopus 로고    scopus 로고
    • New designer drug (1-(1-phenylcyclohexyl)-3-ethoxypropylamine (PCEPA): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry
    • Sauer C., Peters F.T., Staack R.F., Fritschi G., and Maurer H.H. New designer drug (1-(1-phenylcyclohexyl)-3-ethoxypropylamine (PCEPA): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J Mass Spectrom 41 (2006) 1014-1029
    • (2006) J Mass Spectrom , vol.41 , pp. 1014-1029
    • Sauer, C.1    Peters, F.T.2    Staack, R.F.3    Fritschi, G.4    Maurer, H.H.5
  • 9
    • 40649125544 scopus 로고    scopus 로고
    • New designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine (PCEEA) and N-(1-phenylcyclohexyl)-2-methoxyethanamine (PCMEA): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques
    • Sauer C., Peters F.T., Staack R.F., Fritschi G., and Maurer H.H. New designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine (PCEEA) and N-(1-phenylcyclohexyl)-2-methoxyethanamine (PCMEA): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J Mass Spectrom 43 (2008) 305-316
    • (2008) J Mass Spectrom , vol.43 , pp. 305-316
    • Sauer, C.1    Peters, F.T.2    Staack, R.F.3    Fritschi, G.4    Maurer, H.H.5
  • 10
    • 54349117666 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of the designer drug N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA) in rat urine using gas chromatography-mass spectrometry
    • Sauer C., Peters F.T., Staack R.F., Fritschi G., and Maurer HH. Metabolism and toxicological detection of the designer drug N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA) in rat urine using gas chromatography-mass spectrometry. Forensic Sci Int 181 (2009) 47-51
    • (2009) Forensic Sci Int , vol.181 , pp. 47-51
    • Sauer, C.1    Peters, F.T.2    Staack, R.F.3    Fritschi, G.4    Maurer HH5
  • 11
    • 0023029004 scopus 로고
    • Phenylcyclohexylamine: effect of a metabolite of phencyclidine on the efflux of dopamine in the rat
    • Takeda H., Gazzara R.A., and Howard S.G. Phenylcyclohexylamine: effect of a metabolite of phencyclidine on the efflux of dopamine in the rat. Neuropharmacology 25 (1986) 1341-1345
    • (1986) Neuropharmacology , vol.25 , pp. 1341-1345
    • Takeda, H.1    Gazzara, R.A.2    Howard, S.G.3
  • 12
    • 58249142504 scopus 로고    scopus 로고
    • Isolation and purification of the designer drug metabolite O-deethyl-(1-phenylcyclohexyl)-3-ethoxypropanamine (O-deethyl-PCEPA)-biotechnologically synthesized using fission yeast expressing CYP2D6
    • Pragst F., and Aderjan R. (Eds). Mosbach, Germany, April 18-21, 2007. Bad Vilbel (Germany): GTFCH
    • Peters F.T., Schwaninger A.E., Dragan C.A., Sauer C., Fritschi G., Bureik M., et al. Isolation and purification of the designer drug metabolite O-deethyl-(1-phenylcyclohexyl)-3-ethoxypropanamine (O-deethyl-PCEPA)-biotechnologically synthesized using fission yeast expressing CYP2D6. In: Pragst F., and Aderjan R. (Eds). Current Contributions to Forensic and Clinical Toxicology, Proceedings of the XVth GTFCh Symposium. Mosbach, Germany, April 18-21, 2007. Bad Vilbel (Germany): GTFCH (2008) 204-210
    • (2008) Current Contributions to Forensic and Clinical Toxicology, Proceedings of the XVth GTFCh Symposium , pp. 204-210
    • Peters, F.T.1    Schwaninger, A.E.2    Dragan, C.A.3    Sauer, C.4    Fritschi, G.5    Bureik, M.6
  • 13
    • 55949120153 scopus 로고    scopus 로고
    • Identification of cytochrome P450 enzymes involved in the metabolism of the designer drugs N-(1-phenylcyclohexyl)-3-ethoxypropanamine (PCEPA) and N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA)
    • Sauer C., Peters F.T., Schwaninger A.E., Meyer M.R., and Maurer H.H. Identification of cytochrome P450 enzymes involved in the metabolism of the designer drugs N-(1-phenylcyclohexyl)-3-ethoxypropanamine (PCEPA) and N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA). Chem Res Toxicol 21 (2008) 1949-1955
    • (2008) Chem Res Toxicol , vol.21 , pp. 1949-1955
    • Sauer, C.1    Peters, F.T.2    Schwaninger, A.E.3    Meyer, M.R.4    Maurer, H.H.5
  • 14
    • 0032428779 scopus 로고    scopus 로고
    • In vitro assessment of human cytochrome P450
    • Clarke S.E. In vitro assessment of human cytochrome P450. Xenobiotica 28 (1998) 1167-1202
    • (1998) Xenobiotica , vol.28 , pp. 1167-1202
    • Clarke, S.E.1
  • 15
    • 0032866401 scopus 로고    scopus 로고
    • The use of heterologously expressed drug metabolizing enzymes-state of the art and prospects for the future
    • Crespi C.L., and Miller V.P. The use of heterologously expressed drug metabolizing enzymes-state of the art and prospects for the future. Pharmacol Ther 84 (1999) 121-131
    • (1999) Pharmacol Ther , vol.84 , pp. 121-131
    • Crespi, C.L.1    Miller, V.P.2
  • 16
    • 0033674502 scopus 로고    scopus 로고
    • Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches
    • Venkatakrishnan K., von Moltke L.L., Court M.H., Harmatz J.S., Crespi C.L., and Greenblatt D.J. Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metab Dispos 28 (2000) 1493-1504
    • (2000) Drug Metab Dispos , vol.28 , pp. 1493-1504
    • Venkatakrishnan, K.1    von Moltke, L.L.2    Court, M.H.3    Harmatz, J.S.4    Crespi, C.L.5    Greenblatt, D.J.6
  • 17
    • 0028674392 scopus 로고
    • Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research
    • Testa B., and Meyer U.A. (Eds), Academic Press, London
    • Crespi C.L. Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research. In: Testa B., and Meyer U.A. (Eds). Advances in Drug Research. 26th ed. (1995), Academic Press, London 179-235
    • (1995) Advances in Drug Research. 26th ed. , pp. 179-235
    • Crespi, C.L.1
  • 18
    • 0030627339 scopus 로고    scopus 로고
    • Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions
    • Crespi C.L., and Penman B.W. Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions. Adv Pharmacol 43 (1997) 171-188
    • (1997) Adv Pharmacol , vol.43 , pp. 171-188
    • Crespi, C.L.1    Penman, B.W.2
  • 19
    • 58249141655 scopus 로고    scopus 로고
    • Comparative studies on the metabolism and the detection of phencyclidine-derived designer drugs in rat urine using GC-MS techniques
    • Pragst F., and Aderjan R. (Eds). Mosbach, Germany, April 18-21, 2007. Bad Vilbel (Germany): GTFCh
    • Sauer C., Peters F.T., Staack R.F., Fritschi G., and Maurer H.H. Comparative studies on the metabolism and the detection of phencyclidine-derived designer drugs in rat urine using GC-MS techniques. In: Pragst F., and Aderjan R. (Eds). Current Contributions to Forensic and Clinical Toxicology, Proceedings of the XVth GTFCh Symposium. Mosbach, Germany, April 18-21, 2007. Bad Vilbel (Germany): GTFCh (2008) 204-210
    • (2008) Current Contributions to Forensic and Clinical Toxicology, Proceedings of the XVth GTFCh Symposium , pp. 204-210
    • Sauer, C.1    Peters, F.T.2    Staack, R.F.3    Fritschi, G.4    Maurer, H.H.5
  • 20
    • 34047233676 scopus 로고    scopus 로고
    • New potent and selective cytochrome P450 2B6 (CYP2B6) inhibitors based on three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis
    • Korhonen L.E., Turpeinen M., Rahnasto M., Wittekindt C., Poso A., Pelkonen O., et al. New potent and selective cytochrome P450 2B6 (CYP2B6) inhibitors based on three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis. Br J Pharmacol 150 (2007) 932-942
    • (2007) Br J Pharmacol , vol.150 , pp. 932-942
    • Korhonen, L.E.1    Turpeinen, M.2    Rahnasto, M.3    Wittekindt, C.4    Poso, A.5    Pelkonen, O.6
  • 21
    • 0028858960 scopus 로고
    • Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • Newton D.J., Wang R.W., and Lu A.Y. Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 23 (1995) 154-158
    • (1995) Drug Metab Dispos , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.3
  • 22
    • 0030430033 scopus 로고    scopus 로고
    • Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes
    • Bourrie M., Meunier V., Berger Y., and Fabre G. Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277 (1996) 321-332
    • (1996) J Pharmacol Exp Ther , vol.277 , pp. 321-332
    • Bourrie, M.1    Meunier, V.2    Berger, Y.3    Fabre, G.4
  • 23
    • 0029867317 scopus 로고    scopus 로고
    • Formation of (R)-8-hydroxywarfarin in human liver microsomes: a new metabolic marker for the (S)-mephenytoin hydroxylase. P4502C19
    • Wienkers L.C., Wurden C.J., Storch E., Kunze K.L., Rettie A.E., and Trager W.F. Formation of (R)-8-hydroxywarfarin in human liver microsomes: a new metabolic marker for the (S)-mephenytoin hydroxylase. P4502C19. Drug Metab Dispos 24 (1996) 610-614
    • (1996) Drug Metab Dispos , vol.24 , pp. 610-614
    • Wienkers, L.C.1    Wurden, C.J.2    Storch, E.3    Kunze, K.L.4    Rettie, A.E.5    Trager, W.F.6
  • 24
    • 0034004083 scopus 로고    scopus 로고
    • Effects of the antifungal agents on oxidative drug metabolism. Clinical relevance
    • Venkatakrishnan K., von Moltke L.L., and Greenblatt D.J. Effects of the antifungal agents on oxidative drug metabolism. Clinical relevance. Clin Pharmacokinet 38 (2000) 111-180
    • (2000) Clin Pharmacokinet , vol.38 , pp. 111-180
    • Venkatakrishnan, K.1    von Moltke, L.L.2    Greenblatt, D.J.3
  • 25
    • 58249143161 scopus 로고    scopus 로고
    • U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research (CBER). Guidance for Industry: Drug interaction studies-study design, data analysis, and implications for dosing and labeling [draft] 2006.
    • U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research (CBER). Guidance for Industry: Drug interaction studies-study design, data analysis, and implications for dosing and labeling [draft] 2006.
  • 26
    • 33846577441 scopus 로고    scopus 로고
    • Drug interaction studies: study design, data analysis, and implications for dosing and labeling
    • Huang S.M., Temple R., Throckmorton D.C., and Lesko L.J. Drug interaction studies: study design, data analysis, and implications for dosing and labeling. Clin Pharmacol Ther 81 (2007) 298-304
    • (2007) Clin Pharmacol Ther , vol.81 , pp. 298-304
    • Huang, S.M.1    Temple, R.2    Throckmorton, D.C.3    Lesko, L.J.4
  • 27
    • 35548948469 scopus 로고    scopus 로고
    • Use of isolated hepatocyte preparations for cytochrome P450 inhibition studies: comparison with microsomes for Ki determination
    • Brown H.S., Chadwick A., and Houston J.B. Use of isolated hepatocyte preparations for cytochrome P450 inhibition studies: comparison with microsomes for Ki determination. Drug Metab Dispos 35 (2007) 2119-2126
    • (2007) Drug Metab Dispos , vol.35 , pp. 2119-2126
    • Brown, H.S.1    Chadwick, A.2    Houston, J.B.3
  • 28
    • 0018882034 scopus 로고
    • Gas-chromatographic analysis for phencyclidine in plasma, with use of a nitrogen detector
    • Bailey D.N., and Guba J.J. Gas-chromatographic analysis for phencyclidine in plasma, with use of a nitrogen detector. Clin Chem 26 (1980) 437-440
    • (1980) Clin Chem , vol.26 , pp. 437-440
    • Bailey, D.N.1    Guba, J.J.2
  • 29
    • 0022931486 scopus 로고
    • Legal issues associated with PCP abuse-the role of the forensic expert
    • Lerner S.E., and Burns R.S. Legal issues associated with PCP abuse-the role of the forensic expert. NIDA Res Monogr 64 (1986) 229-236
    • (1986) NIDA Res Monogr , vol.64 , pp. 229-236
    • Lerner, S.E.1    Burns, R.S.2
  • 30
    • 33749453826 scopus 로고    scopus 로고
    • The functional role of CYP2B6 in human drug metabolism: substrates and inhibitors in vitro, in vivo and in silico
    • Turpeinen M., Raunio H., and Pelkonen O. The functional role of CYP2B6 in human drug metabolism: substrates and inhibitors in vitro, in vivo and in silico. Curr Drug Metab 7 (2006) 705-714
    • (2006) Curr Drug Metab , vol.7 , pp. 705-714
    • Turpeinen, M.1    Raunio, H.2    Pelkonen, O.3
  • 31
    • 0036237885 scopus 로고    scopus 로고
    • Triethylenethiophosphoramide is a specific inhibitor of cytochrome P450 2B6: implications for cyclophosphamide metabolism
    • Rae J.M., Soukhova N.V., Flockhart D.A., and Desta Z. Triethylenethiophosphoramide is a specific inhibitor of cytochrome P450 2B6: implications for cyclophosphamide metabolism. Drug Metab Dispos 30 (2002) 525-530
    • (2002) Drug Metab Dispos , vol.30 , pp. 525-530
    • Rae, J.M.1    Soukhova, N.V.2    Flockhart, D.A.3    Desta, Z.4
  • 32
    • 0033820249 scopus 로고    scopus 로고
    • CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants
    • Hesse L.M., Venkatakrishnan K., Court M.H., von Moltke L.L., Duan S.X., Shader R.I., et al. CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug Metab Dispos 28 (2000) 1176-1183
    • (2000) Drug Metab Dispos , vol.28 , pp. 1176-1183
    • Hesse, L.M.1    Venkatakrishnan, K.2    Court, M.H.3    von Moltke, L.L.4    Duan, S.X.5    Shader, R.I.6


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