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Volumn 55, Issue 22, 2012, Pages 9773-9784

Haloarene derivatives of carbamazepine with reduced bioactivation liabilities: 2-monohalo and 2,8-dihalo derivatives

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOCARBAMAZEPINE; 2 CHLORO 10,11 DIHYDRO 5H DIBENZ[B,F ]AZEPINE; 2 CHLORO 5H DIBENZ[B,F ]AZEPINE; 2 CHLOROCARBAMAZEPINE; 2 FLUOROCARBAMAZEPINE; 2,8 DIBROMOCARBAMAZEPINE; 2,8 DICHLOROCARBAMAZEPINE; 2,8 DIFLUOROCARBAMAZEPINE; CARBAMAZEPINE; DIBENZAZEPINE DERIVATIVE; GLUTATHIONE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

EID: 84870014766     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301013n     Document Type: Article
Times cited : (17)

References (81)
  • 3
    • 80053004364 scopus 로고    scopus 로고
    • Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: A perspective based on the critical examination of trends in the top 200 drugs marketed in the United States
    • Stepan, A. F.; Walker, D. P.; Bauman, J.; Price, D. A.; Baillie, T. A.; Kalgutkar, A. S.; Aleo, M. D. Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: a perspective based on the critical examination of trends in the top 200 drugs marketed in the United States Chem. Res. Toxicol. 2011, 24, 1345-1410
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 1345-1410
    • Stepan, A.F.1    Walker, D.P.2    Bauman, J.3    Price, D.A.4    Baillie, T.A.5    Kalgutkar, A.S.6    Aleo, M.D.7
  • 5
    • 0029584768 scopus 로고
    • Carbamazepine clinical pharmacology: A review
    • Albani, F.; Riva, R.; Baruzzi, A. Carbamazepine clinical pharmacology: a review Pharmacopsychiatry 1995, 28, 235-244
    • (1995) Pharmacopsychiatry , vol.28 , pp. 235-244
    • Albani, F.1    Riva, R.2    Baruzzi, A.3
  • 7
    • 53549124403 scopus 로고    scopus 로고
    • Hepatotoxicity associated with antiepileptic drugs
    • Bjornsson, E. Hepatotoxicity associated with antiepileptic drugs Acta Neurol. Scand. 2008, 118, 281-290
    • (2008) Acta Neurol. Scand. , vol.118 , pp. 281-290
    • Bjornsson, E.1
  • 8
    • 0028222385 scopus 로고
    • Investigation of mechanisms in toxic epidermal necrolysis induced by carbamazepine
    • Friedmann, P. S.; Strickland, I.; Pirmohamed, M.; Park, B. K. Investigation of mechanisms in toxic epidermal necrolysis induced by carbamazepine Arch. Dermatol. 1994, 130, 598-604
    • (1994) Arch. Dermatol. , vol.130 , pp. 598-604
    • Friedmann, P.S.1    Strickland, I.2    Pirmohamed, M.3    Park, B.K.4
  • 9
    • 0026503611 scopus 로고
    • An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro
    • Pirmohamed, M.; Kitteringham, N. R.; Guenthner, T. M.; Breckenridge, A. M.; Park, B. K. An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro Biochem. Pharmacol. 1992, 43, 1675-1682
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 1675-1682
    • Pirmohamed, M.1    Kitteringham, N.R.2    Guenthner, T.M.3    Breckenridge, A.M.4    Park, B.K.5
  • 10
    • 0026676057 scopus 로고
    • The effect of enzyme induction on the cytochrome P450-mediated bioactivation of carbamazepine by mouse liver microsomes
    • Pirmohamed, M.; Kitteringham, N. R.; Breckenridge, A. M.; Park, B. K. The effect of enzyme induction on the cytochrome P450-mediated bioactivation of carbamazepine by mouse liver microsomes Biochem. Pharmacol. 1992, 44, 2307-2314
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 2307-2314
    • Pirmohamed, M.1    Kitteringham, N.R.2    Breckenridge, A.M.3    Park, B.K.4
  • 12
  • 13
    • 0030968046 scopus 로고    scopus 로고
    • Characterization of the metabolites of carbamazepine in patient urine by liquid chromatography/mass spectrometry
    • Maggs, J. L.; Pirmohamed, M.; Kitteringham, N. R.; Park, B. K. Characterization of the metabolites of carbamazepine in patient urine by liquid chromatography/mass spectrometry Drug Metab. Dispos. 1997, 25, 275-280
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 275-280
    • Maggs, J.L.1    Pirmohamed, M.2    Kitteringham, N.R.3    Park, B.K.4
  • 15
    • 0029926719 scopus 로고    scopus 로고
    • Bioactivation of carbamazepine in the rat in vivo. Evidence for the formation of reactive arene oxide(s)
    • Madden, S.; Maggs, J. L.; Park, B. K. Bioactivation of carbamazepine in the rat in vivo. Evidence for the formation of reactive arene oxide(s) Drug Metab. Dispos. 1996, 24, 469-479
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 469-479
    • Madden, S.1    Maggs, J.L.2    Park, B.K.3
  • 16
    • 47949120265 scopus 로고    scopus 로고
    • Pathways of carbamazepine bioactivation in vitro. III. The role of human cytochrome P450 enzymes in the formation of 2,3-dihydroxycarbamazepine
    • Pearce, R. E.; Lu, W.; Wang, Y.; Uetrecht, J. P.; Correia, M. A.; Leeder, J. S. Pathways of carbamazepine bioactivation in vitro. III. The role of human cytochrome P450 enzymes in the formation of 2,3-dihydroxycarbamazepine Drug Metab. Dispos. 2008, 36, 1637-1349
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 1637-1349
    • Pearce, R.E.1    Lu, W.2    Wang, Y.3    Uetrecht, J.P.4    Correia, M.A.5    Leeder, J.S.6
  • 17
    • 0027499718 scopus 로고
    • Carbamazepine metabolism to a reactive intermediate by the myeloperoxidase system of activated neutrophils
    • Furst, S. M.; Uetrecht, J. P. Carbamazepine metabolism to a reactive intermediate by the myeloperoxidase system of activated neutrophils Biochem. Pharmacol. 1993, 45, 1267-1275
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 1267-1275
    • Furst, S.M.1    Uetrecht, J.P.2
  • 18
    • 28144440176 scopus 로고    scopus 로고
    • Pathways of carbamazepine bioactivation in vitro: II. The role of human cytochrome P450 enzymes in the formation of 2-hydroxyiminostilbene
    • Pearce, R. E.; Uetrecht, J. P.; Leeder, J. S. Pathways of carbamazepine bioactivation in vitro: II. The role of human cytochrome P450 enzymes in the formation of 2-hydroxyiminostilbene Drug Metab. Dispos. 2005, 33, 1819-1826
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 1819-1826
    • Pearce, R.E.1    Uetrecht, J.P.2    Leeder, J.S.3
  • 19
    • 28144464500 scopus 로고    scopus 로고
    • Human in vitro glutathionyl and protein adducts of carbamazepine-10,11- epoxide, a stable and pharmacologically active metabolite of carbamazepine
    • Bu, H. Z.; Kang, P.; Deese, A. J.; Zhao, P.; Pool, W. F. Human in vitro glutathionyl and protein adducts of carbamazepine-10,11-epoxide, a stable and pharmacologically active metabolite of carbamazepine Drug Metab. Dispos. 2005, 33, 1920-1924
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 1920-1924
    • Bu, H.Z.1    Kang, P.2    Deese, A.J.3    Zhao, P.4    Pool, W.F.5
  • 20
    • 35348973117 scopus 로고    scopus 로고
    • Identification of primary and sequential bioactivation pathways of carbamazepine in human liver microsomes using liquid chromatography/tandem mass spectrometry
    • Bu, H. Z.; Zhao, P.; Dalvie, D. K.; Pool, W. F. Identification of primary and sequential bioactivation pathways of carbamazepine in human liver microsomes using liquid chromatography/tandem mass spectrometry Rapid Commun. Mass Spectrom. 2007, 21, 3317-3322
    • (2007) Rapid Commun. Mass Spectrom. , vol.21 , pp. 3317-3322
    • Bu, H.Z.1    Zhao, P.2    Dalvie, D.K.3    Pool, W.F.4
  • 22
    • 0036127241 scopus 로고    scopus 로고
    • Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024
    • Ambrósio, A. F.; Soares-da-Silva, P.; Carvalho, C. M.; Carvalho, A. P. Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024 Neurochem. Res. 2002, 27, 121-130
    • (2002) Neurochem. Res. , vol.27 , pp. 121-130
    • Ambrósio, A.F.1    Soares-Da-Silva, P.2    Carvalho, C.M.3    Carvalho, A.P.4
  • 25
    • 59649106977 scopus 로고    scopus 로고
    • Recent advances in applications of liquid chromatography-tandem mass spectrometry to the analysis of reactive drug metabolites
    • Ma, S.; Zhu, M. Recent advances in applications of liquid chromatography-tandem mass spectrometry to the analysis of reactive drug metabolites Chem.-Biol. Interact. 2009, 179, 25-37
    • (2009) Chem.-Biol. Interact. , vol.179 , pp. 25-37
    • Ma, S.1    Zhu, M.2
  • 26
    • 0026548738 scopus 로고
    • The metabolism of 2- and 4-fluoro-17 β-oestradiol in the rat and its implications for oestrogen carcinogenesis
    • Morgan, P.; Maggs, J. L.; Bulman-Page, P. C.; Hussain, F.; Park, B. K. The metabolism of 2- and 4-fluoro-17 β-oestradiol in the rat and its implications for oestrogen carcinogenesis Biochem. Pharmacol. 1992, 43, 985-993
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 985-993
    • Morgan, P.1    Maggs, J.L.2    Bulman-Page, P.C.3    Hussain, F.4    Park, B.K.5
  • 27
    • 0026457779 scopus 로고
    • Oxidative dehalogenation of 2-fluoro-17α-ethynyloestradiol in vivo. A distal structure-metabolism relationship of 17 α-ethynylation
    • Morgan, P.; Maggs, J. L.; Page, P. C.; Park, B. K. Oxidative dehalogenation of 2-fluoro-17α-ethynyloestradiol in vivo. A distal structure-metabolism relationship of 17 α-ethynylation Biochem. Pharmacol. 1992, 44, 1717-1724
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 1717-1724
    • Morgan, P.1    Maggs, J.L.2    Page, P.C.3    Park, B.K.4
  • 28
    • 0036130782 scopus 로고    scopus 로고
    • Delineating novel metabolic pathways of DPC 963, a non-nucleoside reverse transcriptase inhibitor, in rats. Characterization of glutathione conjugates of postulated oxirene and benzoquinone imine intermediates by LC/MS and LC/NMR
    • Chen, H.; Shockcor, J.; Chen, W.; Espina, R.; Gan, L. S.; Mutlib, A. E. Delineating novel metabolic pathways of DPC 963, a non-nucleoside reverse transcriptase inhibitor, in rats. Characterization of glutathione conjugates of postulated oxirene and benzoquinone imine intermediates by LC/MS and LC/NMR Chem. Res. Toxicol. 2002, 15, 388-399
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 388-399
    • Chen, H.1    Shockcor, J.2    Chen, W.3    Espina, R.4    Gan, L.S.5    Mutlib, A.E.6
  • 29
    • 0000462239 scopus 로고
    • Dibenz[ b, f ]azepines and related ring systems
    • Kricka, L. J.; Ledwith, A. Dibenz[ b, f ]azepines and related ring systems Chem. Rev. 1974, 74, 101-123
    • (1974) Chem. Rev. , vol.74 , pp. 101-123
    • Kricka, L.J.1    Ledwith, A.2
  • 30
    • 0014573174 scopus 로고
    • Synthesis of some substituted 5 H -dibenz[ b, f ]azepines as potent antimalarials
    • Varma, R. S.; Whisenant, L. K.; Boykin, D. W. Synthesis of some substituted 5 H -dibenz[ b, f ]azepines as potent antimalarials J. Med. Chem. 1969, 12, 913-914
    • (1969) J. Med. Chem. , vol.12 , pp. 913-914
    • Varma, R.S.1    Whisenant, L.K.2    Boykin, D.W.3
  • 32
    • 84870009320 scopus 로고
    • Analgesic and anticonvulsant activity of derivatives of dibenz(b, f)azepine
    • In; Soulairac, A. Cahn, J. Charpentier, J. Academic Press: London, U.K.
    • Theobald, W.; Wilhelmi, G.; Krupp, P. Analgesic and anticonvulsant activity of derivatives of dibenz(b, f)azepine. In Pain; Soulairac, A.; Cahn, J.; Charpentier, J., Eds.; Academic Press: London, U.K., 1968; pp 239-249.
    • (1968) Pain , pp. 239-249
    • Theobald, W.1    Wilhelmi, G.2    Krupp, P.3
  • 33
    • 0032905586 scopus 로고    scopus 로고
    • Synthesis of substituted 10,11-dihydro-5 H -dibenz[ b,f ]azepines: Key synthons in syntheses of pharmaceutically active compounds
    • Jørgensen, T. K.; Andersen, K. E.; Lau, J.; Madsen, P.; Huusfeldt, P. O. Synthesis of substituted 10,11-dihydro-5 H -dibenz[ b,f ]azepines: key synthons in syntheses of pharmaceutically active compounds J. Heterocycl. Chem. 1999, 36, 57-64
    • (1999) J. Heterocycl. Chem. , vol.36 , pp. 57-64
    • Jørgensen, T.K.1    Andersen, K.E.2    Lau, J.3    Madsen, P.4    Huusfeldt, P.O.5
  • 34
    • 84981836035 scopus 로고
    • Über derivate des iminodibenzyls iminostilben-derivate
    • Schindler, W.; Blattner, H. Über derivate des iminodibenzyls iminostilben-derivate Helv. Chim. Acta 1961, 44, 753-762
    • (1961) Helv. Chim. Acta , vol.44 , pp. 753-762
    • Schindler, W.1    Blattner, H.2
  • 35
    • 0026674893 scopus 로고
    • A new method for the bromination of carbazoles, β-carbolines and iminodibenzyls by use of N- bromosuccinimide and silica gel
    • Smith, K.; James, D. M.; Mistry, A. G.; Bye, M. R.; Faulkner, D. J. A new method for the bromination of carbazoles, β-carbolines and iminodibenzyls by use of N- bromosuccinimide and silica gel Tetrahedron 1992, 48, 7479-7488
    • (1992) Tetrahedron , vol.48 , pp. 7479-7488
    • Smith, K.1    James, D.M.2    Mistry, A.G.3    Bye, M.R.4    Faulkner, D.J.5
  • 36
    • 45749087007 scopus 로고
    • Reaction of 8H-furo[3,4-d]dibenz[b,f]azepine and 9H-tribenz[b,d,f]azepine with t-butyl hypochlorite and silver trifluoroacetate. Attempts to form a long-lived aromatic nitrenium ion
    • Axtell, H. C.; McHugh, K. B.; Cann, M. C. Reaction of 8H-furo[3,4-d]dibenz[b,f]azepine and 9H-tribenz[b,d,f]azepine with t-butyl hypochlorite and silver trifluoroacetate. Attempts to form a long-lived aromatic nitrenium ion Heterocycles 1995, 41, 431-438
    • (1995) Heterocycles , vol.41 , pp. 431-438
    • Axtell, H.C.1    McHugh, K.B.2    Cann, M.C.3
  • 37
    • 0028896024 scopus 로고
    • Rearrangement of 1-arylindoles to 5H-dibenz[b,f]azepines
    • Tokmakov, G. P.; Grandberg, I. I. Rearrangement of 1-arylindoles to 5H-dibenz[b,f]azepines Tetrahedron 1995, 51, 2091-2098
    • (1995) Tetrahedron , vol.51 , pp. 2091-2098
    • Tokmakov, G.P.1    Grandberg, I.I.2
  • 39
    • 13444267274 scopus 로고    scopus 로고
    • Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): Relation to species differences in hepatotoxicity
    • Kenny, J. R.; Maggs, J. L.; Tettey, J. N.; Harrell, A. W.; Parker, S. G.; Clarke, S. E.; Park, B. K. Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity Drug Metab. Dispos. 2005, 33, 271-281
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 271-281
    • Kenny, J.R.1    Maggs, J.L.2    Tettey, J.N.3    Harrell, A.W.4    Parker, S.G.5    Clarke, S.E.6    Park, B.K.7
  • 44
    • 37049135930 scopus 로고
    • Reactions of condensed N -heteroaromatic molecules. Part II. Electrophilic substitution of N -acetylcarbazole, N -acetyl-l0,11-dihydrodibenz[ b,f ]azepine, and derivatives
    • Kricka, L. J.; Ledwith, A. Reactions of condensed N -heteroaromatic molecules. Part II. Electrophilic substitution of N -acetylcarbazole, N -acetyl-l0,11-dihydrodibenz[ b,f ]azepine, and derivatives J. Chem. Soc., Perkin Trans. 1 1973, 859-863
    • (1973) J. Chem. Soc., Perkin Trans. 1 , pp. 859-863
    • Kricka, L.J.1    Ledwith, A.2
  • 45
    • 0000462239 scopus 로고
    • Dibenz[ b,f ]azepines and related systems
    • Kricka, L. J.; Ledwith, A. Dibenz[ b,f ]azepines and related systems Chem. Rev. 1974, 74, 101-123
    • (1974) Chem. Rev. , vol.74 , pp. 101-123
    • Kricka, L.J.1    Ledwith, A.2
  • 46
    • 84870043036 scopus 로고    scopus 로고
    • Ph.D. thesis, University of Liverpool
    • Elliot, E.-C. Ph.D. thesis, University of Liverpool, 2011.
    • (2011)
    • Elliot, E.-C.1
  • 50
    • 84985715948 scopus 로고
    • Reactions of N - Or N ′-blocked N -acylureas with amines
    • Schweim, H. G. Reactions of N-or N ′-blocked N -acylureas with amines Arch. Pharm. 1987, 320, 430-437
    • (1987) Arch. Pharm. , vol.320 , pp. 430-437
    • Schweim, H.G.1
  • 51
    • 33751428917 scopus 로고    scopus 로고
    • Analogously, trichloroacetyl isocyanate has been used to convert alcohols to carbamates
    • Analogously, trichloroacetyl isocyanate has been used to convert alcohols to carbamates: Narina, S. V.; Kumar, T. S.; George, S.; Sudalai, A. Tetrahedron Lett. 2007, 48, 65-68
    • (2007) Tetrahedron Lett. , vol.48 , pp. 65-68
    • Narina, S.V.1    Kumar, T.S.2    George, S.3    Sudalai, A.4
  • 53
    • 0013844074 scopus 로고
    • Improved synthesis of N, N-diarylureas
    • Durant, G. J. Improved synthesis of N, N-diarylureas Chem. Ind. (London, U. K.) 1965, 1428-1429
    • (1965) Chem. Ind. (London, U. K.) , pp. 1428-1429
    • Durant, G.J.1
  • 54
    • 0034832934 scopus 로고    scopus 로고
    • Tertiary N -glucuronides of clozapine and its metabolite desmethylclozapine in patient urine
    • Breyer-Pfaff, U.; Wachsmuth, H. Tertiary N -glucuronides of clozapine and its metabolite desmethylclozapine in patient urine Drug Metab. Dispos. 2001, 29, 1343-1348
    • (2001) Drug Metab. Dispos. , vol.29 , pp. 1343-1348
    • Breyer-Pfaff, U.1    Wachsmuth, H.2
  • 55
    • 41549150792 scopus 로고    scopus 로고
    • Dual negative precursor ion scan approach for rapid detection of glutathione conjugates using liquid chromatography/tandem mass spectrometry
    • Mahajan, M. K.; Evans, C. A. Dual negative precursor ion scan approach for rapid detection of glutathione conjugates using liquid chromatography/tandem mass spectrometry Rapid Commun. Mass Spectrom. 2008, 22, 1032-1040
    • (2008) Rapid Commun. Mass Spectrom. , vol.22 , pp. 1032-1040
    • Mahajan, M.K.1    Evans, C.A.2
  • 56
    • 0030438701 scopus 로고    scopus 로고
    • Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: Studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene
    • Kitteringham, N. R.; Davis, C.; Howard, N.; Pirmohamed, M.; Park, B. K. Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene J. Pharmacol. Exp. Ther. 1996, 278, 1018-1027
    • (1996) J. Pharmacol. Exp. Ther. , vol.278 , pp. 1018-1027
    • Kitteringham, N.R.1    Davis, C.2    Howard, N.3    Pirmohamed, M.4    Park, B.K.5
  • 57
    • 0029416850 scopus 로고
    • The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man
    • Maggs, J. L.; Williams, D.; Pirmohamed, M.; Park, B. K. The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man J. Pharmacol. Exp. Ther. 1995, 275, 1463-1475
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 1463-1475
    • Maggs, J.L.1    Williams, D.2    Pirmohamed, M.3    Park, B.K.4
  • 58
    • 0028916411 scopus 로고
    • +-glucuronidation of aliphatic tertiary amines in human: Antidepressant versus antipsychotic drugs
    • +-glucuronidation of aliphatic tertiary amines in human: antidepressant versus antipsychotic drugs Xenobiotica 1995, 25, 291-301
    • (1995) Xenobiotica , vol.25 , pp. 291-301
    • Luo, H.1    Hawes, E.M.2    McKay, G.3    Korchinski, E.D.4    Midha, K.K.5
  • 60
    • 0031785952 scopus 로고    scopus 로고
    • Carbamazepine-10,11-epoxide in therapeutic drug monitoring
    • Potter, J. M.; Donnelly, A. Carbamazepine-10,11-epoxide in therapeutic drug monitoring Ther. Drug Monit. 1998, 20, 652-657
    • (1998) Ther. Drug Monit. , vol.20 , pp. 652-657
    • Potter, J.M.1    Donnelly, A.2
  • 61
    • 41149180635 scopus 로고    scopus 로고
    • High-throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry
    • Wen, B.; Ma, L.; Nelson, S. D.; Zhu, M. High-throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry Anal. Chem. 2008, 80, 1788-1799
    • (2008) Anal. Chem. , vol.80 , pp. 1788-1799
    • Wen, B.1    Ma, L.2    Nelson, S.D.3    Zhu, M.4
  • 62
    • 0026615967 scopus 로고
    • 19F-n.m.r. spectroscopy to the identification of dog urinary metabolites of imirestat, a spirohydantoin aldose reductase inhibitor
    • 19F-n.m.r. spectroscopy to the identification of dog urinary metabolites of imirestat, a spirohydantoin aldose reductase inhibitor Xenobiotica 1992, 22, 775-787
    • (1992) Xenobiotica , vol.22 , pp. 775-787
    • Gilbert, P.J.1    Hartley, T.E.2    Troke, J.A.3    Turcan, R.G.4    Vose, C.W.5    Watson, K.V.6
  • 63
    • 0034055226 scopus 로고    scopus 로고
    • Urinary metabolites of a novel quinoxaline non-nucleoside reverse transcriptase inhibitor in rabbit, mouse and human: Identification of fluorine NIH shift metabolites using NMR and tandem MS
    • Dear, G. J.; Ismail, I. M.; Mutch, P. J.; Plumb, R. S.; Davies, L. H.; Sweatman, B. C. Urinary metabolites of a novel quinoxaline non-nucleoside reverse transcriptase inhibitor in rabbit, mouse and human: identification of fluorine NIH shift metabolites using NMR and tandem MS Xenobiotica 2000, 30, 407-426
    • (2000) Xenobiotica , vol.30 , pp. 407-426
    • Dear, G.J.1    Ismail, I.M.2    Mutch, P.J.3    Plumb, R.S.4    Davies, L.H.5    Sweatman, B.C.6
  • 64
    • 0026574227 scopus 로고
    • 3H]17β-oestradiol in the rat: Ring-A dibromination blocks male-specific 15α-hydroxylation and catechol formation
    • 3H]17β-oestradiol in the rat: ring-A dibromination blocks male-specific 15α-hydroxylation and catechol formation J. Steroid Biochem. Mol. Biol. 1992, 42, 77-85
    • (1992) J. Steroid Biochem. Mol. Biol. , vol.42 , pp. 77-85
    • Maggs, J.L.1    Hussain, F.2    Page, P.C.3    Park, B.K.4
  • 66
    • 0030425332 scopus 로고    scopus 로고
    • The biotransformation of clomipramine in vitro, identification of the cytochrome P450s responsible for the separate metabolic pathways
    • Nielsen, K. K.; Flinois, J. P.; Beaune, P.; Brøsen, K. The biotransformation of clomipramine in vitro, identification of the cytochrome P450s responsible for the separate metabolic pathways J. Pharmacol. Exp. Ther. 1996, 277, 1659-1664
    • (1996) J. Pharmacol. Exp. Ther. , vol.277 , pp. 1659-1664
    • Nielsen, K.K.1    Flinois, J.P.2    Beaune, P.3    Brøsen, K.4
  • 67
    • 0031004840 scopus 로고    scopus 로고
    • Influence of substituents in fluorobenzene derivatives on the cytochrome P450-catalyzed hydroxylation at the adjacent ortho aromatic carbon center
    • Koerts, J.; Velraeds, M. M.; Soffers, A. E.; Vervoort, J.; Rietjens, I. M. Influence of substituents in fluorobenzene derivatives on the cytochrome P450-catalyzed hydroxylation at the adjacent ortho aromatic carbon center Chem. Res. Toxicol. 1997, 10, 279-288
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 279-288
    • Koerts, J.1    Velraeds, M.M.2    Soffers, A.E.3    Vervoort, J.4    Rietjens, I.M.5
  • 68
    • 0032589627 scopus 로고    scopus 로고
    • Identification and characterization of efavirenz metabolites by liquid chromatography/mass spectrometry and high field NMR: Species differences in the metabolism of efavirenz
    • Mutlib, A. E.; Chen, H.; Nemeth, G. A.; Markwalder, J. A.; Seitz, S. P.; Gan, L. S.; Christ, D. D. Identification and characterization of efavirenz metabolites by liquid chromatography/mass spectrometry and high field NMR: species differences in the metabolism of efavirenz Drug Metab. Dispos. 1999, 27, 1319-1333
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 1319-1333
    • Mutlib, A.E.1    Chen, H.2    Nemeth, G.A.3    Markwalder, J.A.4    Seitz, S.P.5    Gan, L.S.6    Christ, D.D.7
  • 69
    • 0033010360 scopus 로고    scopus 로고
    • Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism
    • Yang, T. J.; Krausz, K. W.; Sai, Y.; Gonzalez, F. J.; Gelboin, H. V. Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism Drug Metab. Dispos. 1999, 27, 102-109
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 102-109
    • Yang, T.J.1    Krausz, K.W.2    Sai, Y.3    Gonzalez, F.J.4    Gelboin, H.V.5
  • 71
  • 73
    • 77957223212 scopus 로고    scopus 로고
    • Molecular model of anticonvulsant drug binding to the voltage-gated sodium channel inner pore
    • Lipkind, G. M.; Fozzard, H. A. Molecular model of anticonvulsant drug binding to the voltage-gated sodium channel inner pore Mol. Pharmacol. 2010, 78, 631-638
    • (2010) Mol. Pharmacol. , vol.78 , pp. 631-638
    • Lipkind, G.M.1    Fozzard, H.A.2
  • 74
    • 45549087867 scopus 로고    scopus 로고
    • Pharmacodynamics of carbamazepine-mediated induction of CYP3A4, CYP1A2, and Pgp as assessed by probe substrates midazolam, caffeine, and digoxin
    • Magnusson, M. O.; Dahl, M. L.; Cederberg, J.; Karlsson, M. O.; Sandström, R. Pharmacodynamics of carbamazepine-mediated induction of CYP3A4, CYP1A2, and Pgp as assessed by probe substrates midazolam, caffeine, and digoxin Clin. Pharmacol. Ther. 2008, 84, 52-62
    • (2008) Clin. Pharmacol. Ther. , vol.84 , pp. 52-62
    • Magnusson, M.O.1    Dahl, M.L.2    Cederberg, J.3    Karlsson, M.O.4    Sandström, R.5
  • 75
    • 17844403222 scopus 로고    scopus 로고
    • Carbamazepine is an inhibitor of histone deacetylases
    • Beutler, A. S.; Li, S.; Nicol, R.; Walsh, M. J. Carbamazepine is an inhibitor of histone deacetylases Life Sci. 2005, 76, 3107-3115
    • (2005) Life Sci. , vol.76 , pp. 3107-3115
    • Beutler, A.S.1    Li, S.2    Nicol, R.3    Walsh, M.J.4
  • 76
    • 80255134517 scopus 로고    scopus 로고
    • Histone deacetylase 1 is required for carbamazepine-induced CYP3A4 expression
    • Wu, Y.; Shi, X.; Liu, Y.; Zhang, X.; Wang, J.; Luo, X.; Wen, A. Histone deacetylase 1 is required for carbamazepine-induced CYP3A4 expression J. Pharm. Biomed. Anal. 2012, 58, 78-82
    • (2012) J. Pharm. Biomed. Anal. , vol.58 , pp. 78-82
    • Wu, Y.1    Shi, X.2    Liu, Y.3    Zhang, X.4    Wang, J.5    Luo, X.6    Wen, A.7
  • 77
    • 82555205335 scopus 로고    scopus 로고
    • Long-term antiepileptic treatment with histone deacetylase inhibitors may reduce the risk of prostate cancer
    • Stettner, M.; Krämer, G.; Strauss, A.; Kvitkina, T.; Ohle, S.; Kieseier, B. C.; Thelen, P. Long-term antiepileptic treatment with histone deacetylase inhibitors may reduce the risk of prostate cancer Eur. J. Cancer Prev. 2012, 21, 55-64
    • (2012) Eur. J. Cancer Prev. , vol.21 , pp. 55-64
    • Stettner, M.1    Krämer, G.2    Strauss, A.3    Kvitkina, T.4    Ohle, S.5    Kieseier, B.C.6    Thelen, P.7
  • 78
    • 73349116582 scopus 로고    scopus 로고
    • Docking of hydroxamic acids into HDAC1 and HDAC8: A rationalization of activity trends and selectivities
    • Ortore, G.; Di Colo, F.; Martinelli, A. Docking of hydroxamic acids into HDAC1 and HDAC8: a rationalization of activity trends and selectivities J. Chem. Inf. Model. 2009, 49, 2774-2785
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 2774-2785
    • Ortore, G.1    Di Colo, F.2    Martinelli, A.3
  • 79
    • 0017101039 scopus 로고
    • Preparation of isolated rat liver cells
    • Seglen, P. O. Preparation of isolated rat liver cells Methods Cell Biol. 1976, 13, 29-83
    • (1976) Methods Cell Biol. , vol.13 , pp. 29-83
    • Seglen, P.O.1
  • 80
    • 0031914981 scopus 로고    scopus 로고
    • max of carbamazepine and carbamazepine epoxide following a single and multiple dose of a sustained-release product
    • max of carbamazepine and carbamazepine epoxide following a single and multiple dose of a sustained-release product Br. J. Clin. Pharmacol. 1998, 45, 241-246
    • (1998) Br. J. Clin. Pharmacol. , vol.45 , pp. 241-246
    • Mahmood, I.1    Chamberlin, N.2
  • 81
    • 69749121899 scopus 로고    scopus 로고
    • Pharmacokinetic interaction of single dose of piperine with steady-state carbamazepine in epilepsy patients
    • Pattanaik, S.; Hota, D.; Prabhakar, S.; Kharbanda, P.; Pandhi, P. Pharmacokinetic interaction of single dose of piperine with steady-state carbamazepine in epilepsy patients Phytother. Res. 2009, 23, 1281-1286
    • (2009) Phytother. Res. , vol.23 , pp. 1281-1286
    • Pattanaik, S.1    Hota, D.2    Prabhakar, S.3    Kharbanda, P.4    Pandhi, P.5


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