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Volumn 36, Issue 1, 2008, Pages 163-168

Identification of cytochrome P450 enzymes involved in the metabolism of the new designer drug 4′-methyl-α-pyrrolidinobutyrophenone

Author keywords

[No Author keywords available]

Indexed keywords

4' METHYL ALPHA PYRROLIDINOBUTYROPHENONE; ALPHA NAPHTHOFLAVONE; COMPLEMENTARY DNA; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; DESIGNER DRUG; DRUG METABOLITE; FLUCONAZOLE; QUINIDINE; UNCLASSIFIED DRUG;

EID: 37549045269     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.017293     Document Type: Article
Times cited : (17)

References (40)
  • 1
    • 0029028932 scopus 로고
    • Geographical/interracial differences in polymorphic drug oxidation. Current state of knowledge of cytochromes P450 (CYP) 2D6 and 2C19
    • Bertilsson L (1995) Geographical/interracial differences in polymorphic drug oxidation. Current state of knowledge of cytochromes P450 (CYP) 2D6 and 2C19. Clin Pharmacokinet 29:192-209.
    • (1995) Clin Pharmacokinet , vol.29 , pp. 192-209
    • Bertilsson, L.1
  • 2
    • 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 (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277:321-332.
    • (1996) J Pharmacol Exp Ther , vol.277 , pp. 321-332
    • Bourrie, M.1    Meunier, V.2    Berger, Y.3    Fabre, G.4
  • 3
    • 0035198219 scopus 로고    scopus 로고
    • Evidence supporting the interaction of CYP2B4 and CYP1A2 in microsomal preparations
    • Cawley GF, Zhang S, Kelley RW, and Backes WL (2001) Evidence supporting the interaction of CYP2B4 and CYP1A2 in microsomal preparations. Drug Metab Dispos 29:1529-1534.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1529-1534
    • Cawley, G.F.1    Zhang, S.2    Kelley, R.W.3    Backes, W.L.4
  • 4
    • 0032428779 scopus 로고    scopus 로고
    • In vitro assessment of human cytochrome P450
    • Clarke SE (1998) In vitro assessment of human cytochrome P450. Xenobiotica 28:1167-1202.
    • (1998) Xenobiotica , vol.28 , pp. 1167-1202
    • Clarke, S.E.1
  • 5
    • 0028674392 scopus 로고
    • Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research
    • Testa B and Meyer UA eds pp, Academic Press, London
    • Crespi CL (1995) Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research, in Advances in Drug Research (Testa B and Meyer UA eds) pp 179-235, Academic Press, London.
    • (1995) Advances in Drug Research , pp. 179-235
    • Crespi, C.L.1
  • 6
    • 0032866401 scopus 로고    scopus 로고
    • The use of heterologously expressed drug metabolizing enzymes - state of the art and prospects for the future
    • Crespi CL and Miller VP (1999) The use of heterologously expressed drug metabolizing enzymes - state of the art and prospects for the future. Pharmacol Ther 84:121-131.
    • (1999) Pharmacol Ther , vol.84 , pp. 121-131
    • Crespi, C.L.1    Miller, V.P.2
  • 7
    • 0030627339 scopus 로고    scopus 로고
    • Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions
    • Crespi CL and Penman BW (1997) Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions. Adv Pharmacol 43:171-188.
    • (1997) Adv Pharmacol , vol.43 , pp. 171-188
    • Crespi, C.L.1    Penman, B.W.2
  • 8
    • 0026787192 scopus 로고
    • The effect of selective serotonin re-uptake inhibitors on cytochrome P4502D6 (CYP2D6) activity in human liver microsomes
    • Crewe HK, Lennard MS, Tucker GT, Woods FR, and Haddock RE (1992) The effect of selective serotonin re-uptake inhibitors on cytochrome P4502D6 (CYP2D6) activity in human liver microsomes. Br J Clin Pharmacol 34:262-265.
    • (1992) Br J Clin Pharmacol , vol.34 , pp. 262-265
    • Crewe, H.K.1    Lennard, M.S.2    Tucker, G.T.3    Woods, F.R.4    Haddock, R.E.5
  • 10
    • 0017035206 scopus 로고
    • Role of central catecholamines in the psychostimulant activity of pyrovalerone]
    • Fauquet JP, Morel E, Demarty C, and Rapin JR (1976) [Role of central catecholamines in the psychostimulant activity of pyrovalerone]. Arch Int Pharmacodyn Ther 224:325-337.
    • (1976) Arch Int Pharmacodyn Ther , vol.224 , pp. 325-337
    • Fauquet, J.P.1    Morel, E.2    Demarty, C.3    Rapin, J.R.4
  • 11
    • 0015870524 scopus 로고
    • A controlled evaluation of pyrovalerone in chronically fatigued volunteers
    • Goldberg J, Gardos G, and Cole JO (1973) A controlled evaluation of pyrovalerone in chronically fatigued volunteers. Int Pharmacopsychiatry 8:60-69.
    • (1973) Int Pharmacopsychiatry , vol.8 , pp. 60-69
    • Goldberg, J.1    Gardos, G.2    Cole, J.O.3
  • 12
    • 84892246340 scopus 로고    scopus 로고
    • Human cytochrome P450 enzymes
    • Ortiz-de-Montellano PR ed pp, Kluwer Academic/Plenum Publishers, New York
    • Guengerich FP (2005) Human cytochrome P450 enzymes, in Cytochrome P450 - Structure, Mechanism, and Biochemistry (Ortiz-de-Montellano PR ed) pp 377-530, Kluwer Academic/Plenum Publishers, New York.
    • (2005) Cytochrome P450 - Structure, Mechanism, and Biochemistry , pp. 377-530
    • Guengerich, F.P.1
  • 13
    • 11144328243 scopus 로고    scopus 로고
    • Interactions between CYP2C9 and CYP2C19 in reconstituted binary systems influence their catalytic activity: Possible rationale for the inability of CYP2C19 to catalyze methoxychlor demethylation in human liver microsomes
    • Hazai E and Kupfer D (2005) Interactions between CYP2C9 and CYP2C19 in reconstituted binary systems influence their catalytic activity: possible rationale for the inability of CYP2C19 to catalyze methoxychlor demethylation in human liver microsomes. Drug Metab Dispos 33:157-164.
    • (2005) Drug Metab Dispos , vol.33 , pp. 157-164
    • Hazai, E.1    Kupfer, D.2
  • 14
    • 0013855128 scopus 로고
    • Experimental psychological differentiation of the effect of 2 psychostimulants (F-1983 and amphetamine) in humans.]
    • Heimann H and Lukacs G (1965) [Experimental psychological differentiation of the effect of 2 psychostimulants (F-1983 and amphetamine) in humans.] Psychopharmacologia 8:79-90.
    • (1965) Psychopharmacologia , vol.8 , pp. 79-90
    • Heimann, H.1    Lukacs, G.2
  • 15
    • 0011364919 scopus 로고
    • Clinical studies of a new psychostimulant (F-1983).]
    • Heinmann H and Vetter K (1965) [Clinical studies of a new psychostimulant (F-1983).] Schweiz Med Wochenschr 95:306-309.
    • (1965) Schweiz Med Wochenschr , vol.95 , pp. 306-309
    • Heinmann, H.1    Vetter, K.2
  • 16
    • 0001594153 scopus 로고
    • Compound 84/F 1983 compared with D-amphetamine and placebo in regard to effects on human performance
    • Holliday AR, Morris RB, and Sharpley RP (1964) Compound 84/F 1983 compared with D-amphetamine and placebo in regard to effects on human performance. Psychopharmacologia 6:192-200.
    • (1964) Psychopharmacologia , vol.6 , pp. 192-200
    • Holliday, A.R.1    Morris, R.B.2    Sharpley, R.P.3
  • 17
    • 0030572975 scopus 로고    scopus 로고
    • Identification of a pyrovalerone metabolite in the rat by gas chromatography-mass spectrometry and determination of pyrovalerone by gas chromatography-nitrogen-phosphorus detection
    • Lho DS, Lee J, Kim S, Park J, and Shin HS (1996) Identification of a pyrovalerone metabolite in the rat by gas chromatography-mass spectrometry and determination of pyrovalerone by gas chromatography-nitrogen-phosphorus detection. J Chromatogr B Biomed Appl 687:253-259.
    • (1996) J Chromatogr B Biomed Appl , vol.687 , pp. 253-259
    • Lho, D.S.1    Lee, J.2    Kim, S.3    Park, J.4    Shin, H.S.5
  • 18
    • 0036316746 scopus 로고    scopus 로고
    • Validated assay for quantification of oxcarbazepine and its active dihydro metabolite 10-hydroxy carbazepine in plasma by atmospheric pressure chemical ionization liquid chromatography/mass spectrometry
    • Maurer HH, Kratzsch C, Weber AA, Peters FT, and Kraemer T (2002) Validated assay for quantification of oxcarbazepine and its active dihydro metabolite 10-hydroxy carbazepine in plasma by atmospheric pressure chemical ionization liquid chromatography/mass spectrometry. J Mass Spectrom 37:687-692.
    • (2002) J Mass Spectrom , vol.37 , pp. 687-692
    • Maurer, H.H.1    Kratzsch, C.2    Weber, A.A.3    Peters, F.T.4    Kraemer, T.5
  • 19
    • 33144477907 scopus 로고    scopus 로고
    • 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors
    • Meltzer PC, Butler D, Deschamps JR, and Madras BK (2006) 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. J Med Chem 49:1420-1432.
    • (2006) J Med Chem , vol.49 , pp. 1420-1432
    • Meltzer, P.C.1    Butler, D.2    Deschamps, J.R.3    Madras, B.K.4
  • 20
    • 0014792608 scopus 로고
    • The metabolism of pyrovalerone hydrochloride
    • Michaelis W, Russel JH, and Schindler O (1970) The metabolism of pyrovalerone hydrochloride. J Med Chem 13:497-503.
    • (1970) J Med Chem , vol.13 , pp. 497-503
    • Michaelis, W.1    Russel, J.H.2    Schindler, O.3
  • 21
    • 0028858960 scopus 로고
    • Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • Newton DJ, Wang RW, and Lu AY (1995) Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 23:154-158.
    • (1995) Drug Metab Dispos , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.3
  • 22
    • 34250716024 scopus 로고    scopus 로고
    • Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinobutyrophenone
    • Peters FT, Dragan CA, Wilde DR, Meyer MR, Bureik M, and Maurer HH (2007) Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinobutyrophenone. Biochem Pharmacol 74:511-520.
    • (2007) Biochem Pharmacol , vol.74 , pp. 511-520
    • Peters, F.T.1    Dragan, C.A.2    Wilde, D.R.3    Meyer, M.R.4    Bureik, M.5    Maurer, H.H.6
  • 23
    • 24044529175 scopus 로고    scopus 로고
    • Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinobutyrophenone (MPBP) in urine using gas chromatography-mass spectrometry
    • Peters FT, Meyer MR, Fritschi G, and Maurer HH (2005) Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinobutyrophenone (MPBP) in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 824:81-91.
    • (2005) J Chromatogr B Analyt Technol Biomed Life Sci , vol.824 , pp. 81-91
    • Peters, F.T.1    Meyer, M.R.2    Fritschi, G.3    Maurer, H.H.4
  • 25
    • 0018164876 scopus 로고
    • Effects of pyrovalerone on peripheral noradrenergic mechanisms
    • Servin A, Fauquet JP, Jacquot C, and Rapin JR (1978) Effects of pyrovalerone on peripheral noradrenergic mechanisms. Biochem Pharmacol 27:1693-1694.
    • (1978) Biochem Pharmacol , vol.27 , pp. 1693-1694
    • Servin, A.1    Fauquet, J.P.2    Jacquot, C.3    Rapin, J.R.4
  • 26
    • 0029837492 scopus 로고    scopus 로고
    • Detection and identification of pyrovalerone and its hydroxylated metabolite in the rat
    • Shin HS, Shin YS, Lee S, and Park BB (1996) Detection and identification of pyrovalerone and its hydroxylated metabolite in the rat. J Anal Toxicol 20:568-572.
    • (1996) J Anal Toxicol , vol.20 , pp. 568-572
    • Shin, H.S.1    Shin, Y.S.2    Lee, S.3    Park, B.B.4
  • 27
    • 0032444641 scopus 로고    scopus 로고
    • Human cytochrome P450s: Selectivity and measurement in vivo
    • Smith DA, Abel SM, Hyland R, and Jones BC (1998) Human cytochrome P450s: selectivity and measurement in vivo. Xenobiotica 28:1095-1128.
    • (1998) Xenobiotica , vol.28 , pp. 1095-1128
    • Smith, D.A.1    Abel, S.M.2    Hyland, R.3    Jones, B.C.4
  • 28
    • 0017122856 scopus 로고
    • The psychotropic effect of the Pyrovalerone (F-1983), placebo, the milieu therapy and mental condition of the patients in forensic psychiatry]
    • Soderholm S, Viukari NM, and Rimon R (1976) [The psychotropic effect of the Pyrovalerone (F-1983), placebo, the milieu therapy and mental condition of the patients in forensic psychiatry]. Nervenarzt 47:88-93.
    • (1976) Nervenarzt , vol.47 , pp. 88-93
    • Soderholm, S.1    Viukari, N.M.2    Rimon, R.3
  • 29
    • 0142122818 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of the new designer drug 3′,4′- methylenedioxy-alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry
    • Springer D, Fritschi G, and Maurer HH (2003a) Metabolism and toxicological detection of the new designer drug 3′,4′- methylenedioxy-alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 793:377-388.
    • (2003) J Chromatogr B Analyt Technol Biomed Life Sci , vol.793 , pp. 377-388
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 30
    • 0142091104 scopus 로고    scopus 로고
    • Metabolism and toxicological detection of the new designer drug 4′-methoxy-α- pyrrolidinopropiophenone studied in rat urine using gas chromatography-mass spectrometry
    • Springer D, Fritschi G, and Maurer HH (2003b) Metabolism and toxicological detection of the new designer drug 4′-methoxy-α- pyrrolidinopropiophenone studied in rat urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 793:331-342.
    • (2003) J Chromatogr B Analyt Technol Biomed Life Sci , vol.793 , pp. 331-342
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 31
    • 0142165136 scopus 로고    scopus 로고
    • Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in urine using gas chromatography-mass spectrometry
    • Springer D, Fritschi G, and Maurer HH (2003c) Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 796:253-266.
    • (2003) J Chromatogr B Analyt Technol Biomed Life Sci , vol.796 , pp. 253-266
    • Springer, D.1    Fritschi, G.2    Maurer, H.H.3
  • 32
    • 0042025298 scopus 로고    scopus 로고
    • Identification of the cytochrome P450 enzymes involved in the metabolism of 4′-methyl-(alpha)-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes
    • Springer D, Paul LD, Staack RF, Kraemer T, and Maurer HH (2003d) Identification of the cytochrome P450 enzymes involved in the metabolism of 4′-methyl-(alpha)-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes. Drug Metab Dispos 31:979-982.
    • (2003) Drug Metab Dispos , vol.31 , pp. 979-982
    • Springer, D.1    Paul, L.D.2    Staack, R.F.3    Kraemer, T.4    Maurer, H.H.5
  • 33
    • 37549070478 scopus 로고    scopus 로고
    • Springer D, Paul LD, Staack RF, Kraemer T and Maurer HH (2003e) Involvement of human hepatic cytochrome P450 isoenzymes in the metabolism of the new pyrrolidinophenone designer drugs MPPP, MOPPP, MDPPP and MPHP, in Proceedings of the XIIIth GTFCh Symposium in Mosbach (Pragst F and Aderjan R eds), pp 204-211, Helm-Verlag, Heppenheim (Germany).
    • Springer D, Paul LD, Staack RF, Kraemer T and Maurer HH (2003e) Involvement of human hepatic cytochrome P450 isoenzymes in the metabolism of the new pyrrolidinophenone designer drugs MPPP, MOPPP, MDPPP and MPHP, in Proceedings of the XIIIth GTFCh Symposium in Mosbach (Pragst F and Aderjan R eds), pp 204-211, Helm-Verlag, Heppenheim (Germany).
  • 34
    • 0037420911 scopus 로고    scopus 로고
    • New designer drug 4′-methyl-alpha-pyrrolidinohexanophenone: Studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry
    • Springer D, Peters FT, Fritschi G, and Maurer HH (2003f) New designer drug 4′-methyl-alpha-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 789:79-91.
    • (2003) J Chromatogr B Analyt Technol Biomed Life Sci , vol.789 , pp. 79-91
    • Springer, D.1    Peters, F.T.2    Fritschi, G.3    Maurer, H.H.4
  • 35
    • 0037097028 scopus 로고    scopus 로고
    • Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry
    • Springer D, Peters FT, Fritschi G, and Maurer HH (2002) Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 773:25-33.
    • (2002) J Chromatogr B Analyt Technol Biomed Life Sci , vol.773 , pp. 25-33
    • Springer, D.1    Peters, F.T.2    Fritschi, G.3    Maurer, H.H.4
  • 36
    • 0011276062 scopus 로고
    • Comparative pharmacological study of a new central stimulant, 1-p-tolyl-1-oxo-2-pyrrolidino- n-pentane HCl]
    • Stille G, Ackermann H, Eichenberger E, and Lauener H (1963) [Comparative pharmacological study of a new central stimulant, 1-p-tolyl-1-oxo-2-pyrrolidino- n-pentane HCl]. Arzneim-Forsch 13:871-877.
    • (1963) Arzneim-Forsch , vol.13 , pp. 871-877
    • Stille, G.1    Ackermann, H.2    Eichenberger, E.3    Lauener, H.4
  • 37
    • 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 LL, Court MH, Harmatz JS, Crespi CL, and Greenblatt DJ (2000a) 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 28:1493-1504.
    • (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
  • 38
    • 0034004083 scopus 로고    scopus 로고
    • Effects of the antifungal agents on oxidative drug metabolism. Clinical relevance
    • Venkatakrishnan K, von Moltke LL, and Greenblatt DJ (2000b) Effects of the antifungal agents on oxidative drug metabolism. Clinical relevance. Clin Pharmacokinet 38:111-180.
    • (2000) Clin Pharmacokinet , vol.38 , pp. 111-180
    • Venkatakrishnan, K.1    von Moltke, L.L.2    Greenblatt, D.J.3
  • 39
    • 0035079928 scopus 로고    scopus 로고
    • Application of the relative activity factor approach in scaling from heterologously expressed cytochromes P450 to human liver microsomes: Studies on amitriptyline as a model substrate
    • Venkatakrishnan K, von Moltke LL, and Greenblatt DJ (2001) Application of the relative activity factor approach in scaling from heterologously expressed cytochromes P450 to human liver microsomes: studies on amitriptyline as a model substrate. J Pharmacol Exp Ther 297:326-337.
    • (2001) J Pharmacol Exp Ther , vol.297 , pp. 326-337
    • Venkatakrishnan, K.1    von Moltke, L.L.2    Greenblatt, D.J.3
  • 40
    • 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 LC, Wurden CJ, Storch E, Kunze KL, Rettie AE, and Trager WF (1996) Formation of (R)-8-hydroxywarfarin in human liver microsomes: a new metabolic marker for the (S)-mephenytoin hydroxylase, P4502C19. Drug Metab Dispos 24:610-614.
    • (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


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