메뉴 건너뛰기




Volumn 35, Issue 12, 2007, Pages 2242-2251

Cyclic conversion of the novel Src kinase inhibitor [7-(2,6-dichloro- phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl] -amine (TG100435) and its N-oxide metabolite by flavin-containing monoxygenases and cytochrome P450 reductase

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOBENZOTRIAZOLE; [7 (2,6 DICHLOROPHENYL) 5 METHYLBENZO[1,2,4]TRIAZIN 3 YL][4 (2 PYRROLIDIN 1 YLETHOXY)PHENYL]AMINE; CYTOCHROME P450 REDUCTASE; DEXTROMETHORPHAN; DEXTRORPHAN; DIMETHYLANILINE MONOOXYGENASE; FURAFYLLINE; KETOCONAZOLE; MEPHENYTOIN; MIDAZOLAM; PARACETAMOL; PHENACETIN; PROTEIN TYROSINE KINASE INHIBITOR; QUINIDINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFAPHENAZOLE; TG 100435; TG 100855; THIAMAZOLE; TOLBUTAMIDE; TRANYLCYPROMINE; UNCLASSIFIED DRUG;

EID: 36348967194     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.017384     Document Type: Article
Times cited : (17)

References (36)
  • 1
    • 0033066222 scopus 로고    scopus 로고
    • Utility of hepatocytes to model species differences in the metabolism of loxtidine and to predict pharmacokinetic parameters in rat, dog and man
    • Bayliss MK, Bell JA, Jenner WN, Park GR, and Wilson K (1999) Utility of hepatocytes to model species differences in the metabolism of loxtidine and to predict pharmacokinetic parameters in rat, dog and man. Xenobiotica 29:253-268.
    • (1999) Xenobiotica , vol.29 , pp. 253-268
    • Bayliss, M.K.1    Bell, J.A.2    Jenner, W.N.3    Park, G.R.4    Wilson, K.5
  • 2
    • 0031026558 scopus 로고    scopus 로고
    • Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone, a tobacco-specific lung carcinogen
    • Carmella SG, Borukhova A, Akerkar SA, and Hecht SS (1997) Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone, a tobacco-specific lung carcinogen. Cancer Epidemiol Biomarkers Prev 6:113-120.
    • (1997) Cancer Epidemiol Biomarkers Prev , vol.6 , pp. 113-120
    • Carmella, S.G.1    Borukhova, A.2    Akerkar, S.A.3    Hecht, S.S.4
  • 3
    • 0028945438 scopus 로고
    • Structural and catalytic properties of the mammalian flavin-containing monooxygenase
    • Cashman JR (1995) Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chem Res Toxicol 8:165-181.
    • (1995) Chem Res Toxicol , vol.8 , pp. 165-181
    • Cashman, J.R.1
  • 5
    • 33644645677 scopus 로고    scopus 로고
    • Decrease in NADPH-cytochrome P450 reductase activity of the human heart, liver and lungs in the presence of alpha-lipoic acid
    • Dudka J (2006) Decrease in NADPH-cytochrome P450 reductase activity of the human heart, liver and lungs in the presence of alpha-lipoic acid. Ann Nutr Metab 50:121-125.
    • (2006) Ann Nutr Metab , vol.50 , pp. 121-125
    • Dudka, J.1
  • 6
    • 22544466126 scopus 로고    scopus 로고
    • Activity of NADPH-cytochrome P-450 reductase of the human heart, liver and lungs in the presence of (-)-epigallocatechin gallate, quercetin and resveratrol: An in vitro study
    • Dudka J, Jodynis-Liebert J, Korobowicz E, Burdan F, Korobowicz A, Szumilo J, Tokarska E, Klepacz R, and Murias M (2005) Activity of NADPH-cytochrome P-450 reductase of the human heart, liver and lungs in the presence of (-)-epigallocatechin gallate, quercetin and resveratrol: an in vitro study. Basic Clin Pharmacol Toxicol 97:74-79.
    • (2005) Basic Clin Pharmacol Toxicol , vol.97 , pp. 74-79
    • Dudka, J.1    Jodynis-Liebert, J.2    Korobowicz, E.3    Burdan, F.4    Korobowicz, A.5    Szumilo, J.6    Tokarska, E.7    Klepacz, R.8    Murias, M.9
  • 7
    • 0029834386 scopus 로고    scopus 로고
    • A convenient method to discriminate between cytochrome P450 enzymes and flavin-containing monoxygenases in human liver microsomes
    • Grothusen A, Hardt J, Brautigam L, Lang D, and Bocker R (1996) A convenient method to discriminate between cytochrome P450 enzymes and flavin-containing monoxygenases in human liver microsomes. Arch Toxicol 71:64-71.
    • (1996) Arch Toxicol , vol.71 , pp. 64-71
    • Grothusen, A.1    Hardt, J.2    Brautigam, L.3    Lang, D.4    Bocker, R.5
  • 8
    • 0030854077 scopus 로고    scopus 로고
    • Baculovirus-mediated expression and purification of human FMO3: Catalytic, immunochemical, and structural characterization
    • Haining RL, Hunter AP, Sadeque AJ, Philpot RM, and Rettie AE (1997) Baculovirus-mediated expression and purification of human FMO3: catalytic, immunochemical, and structural characterization. Drug Metab Dispos 25:790-797.
    • (1997) Drug Metab Dispos , vol.25 , pp. 790-797
    • Haining, R.L.1    Hunter, A.P.2    Sadeque, A.J.3    Philpot, R.M.4    Rettie, A.E.5
  • 9
    • 0028265810 scopus 로고
    • The mammalian flavin-containing monooxygenases: Molecular characterization and regulation of expression
    • Hines RN, Cashman JR, Philpot RM, Williams DE, and Ziegler DM (1994) The mammalian flavin-containing monooxygenases: molecular characterization and regulation of expression. Toxicol Appl Pharmacol 125:1-6.
    • (1994) Toxicol Appl Pharmacol , vol.125 , pp. 1-6
    • Hines, R.N.1    Cashman, J.R.2    Philpot, R.M.3    Williams, D.E.4    Ziegler, D.M.5
  • 11
    • 0030886020 scopus 로고    scopus 로고
    • N-Oxygenation of phenethylamine to the trans-oxime by adult human liver flavin-containing monooxygenase and retroreduction of phenethylamine hydroxylamine by human liver microsomes
    • Lin J and Cashman J (1997) N-Oxygenation of phenethylamine to the trans-oxime by adult human liver flavin-containing monooxygenase and retroreduction of phenethylamine hydroxylamine by human liver microsomes. J Pharmacol Exp Ther 282:1269-1279.
    • (1997) J Pharmacol Exp Ther , vol.282 , pp. 1269-1279
    • Lin, J.1    Cashman, J.2
  • 12
    • 0021995799 scopus 로고
    • Loss of rat liver microsomal cytochrome P-450 during methimazole metabolism. Role of flavin-containing monooxygenase
    • Kedderis GL and Rickert DE (1985) Loss of rat liver microsomal cytochrome P-450 during methimazole metabolism. Role of flavin-containing monooxygenase. Drug Metab Dispos 13:58-61.
    • (1985) Drug Metab Dispos , vol.13 , pp. 58-61
    • Kedderis, G.L.1    Rickert, D.E.2
  • 13
    • 0036157094 scopus 로고    scopus 로고
    • Human flavin-containing monooxygenases 1 (FMO1) and 3 developmental expression
    • Koukouritaki SB, Simpson P, Yeung CK, Rettie AE, and Hines RN (2002) Human flavin-containing monooxygenases 1 (FMO1) and 3 developmental expression. Pediatr Res 51:236-243.
    • (2002) Pediatr Res , vol.51 , pp. 236-243
    • Koukouritaki, S.B.1    Simpson, P.2    Yeung, C.K.3    Rettie, A.E.4    Hines, R.N.5
  • 14
    • 0021125391 scopus 로고
    • Increased biliary GSSG efflux from rat liver perfused with thiocarbamamide substrate for the flavin-containing monooxygenases
    • Krieter PA, Ziegler DM, Hill KE, and Burk RF (1984) Increased biliary GSSG efflux from rat liver perfused with thiocarbamamide substrate for the flavin-containing monooxygenases. Mol Pharmacol 26:122-127.
    • (1984) Mol Pharmacol , vol.26 , pp. 122-127
    • Krieter, P.A.1    Ziegler, D.M.2    Hill, K.E.3    Burk, R.F.4
  • 15
    • 33646712592 scopus 로고    scopus 로고
    • The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines
    • Krueger SK, Vandyke JE, Williams DE, and Hines RN (2006) The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines. Drug Metab Rev 38:139-147.
    • (2006) Drug Metab Rev , vol.38 , pp. 139-147
    • Krueger, S.K.1    Vandyke, J.E.2    Williams, D.E.3    Hines, R.N.4
  • 17
    • 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 AYH (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.H.3
  • 18
    • 33846284502 scopus 로고    scopus 로고
    • Discovery of [7-(2,6-dichlorophenyl)- 5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl] amine a potent, orally active Src kinase inhibitor with anti-tumor activity in preclinical assays
    • Noronha G, Barrett K, Boccia A, Brodhag T, Cao J, Chow CP, Dneprovskaia E, Doukas J, Fine R, Gong X, et al. (2007) Discovery of [7-(2,6-dichlorophenyl)- 5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl] amine a potent, orally active Src kinase inhibitor with anti-tumor activity in preclinical assays. Bioorg Med Chem Lett 17:602-608.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 602-608
    • Noronha, G.1    Barrett, K.2    Boccia, A.3    Brodhag, T.4    Cao, J.5    Chow, C.P.6    Dneprovskaia, E.7    Doukas, J.8    Fine, R.9    Gong, X.10
  • 19
    • 0032733974 scopus 로고    scopus 로고
    • Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: An examination of in vitro half-life approach and nonspecific binding to microsomes
    • Obach R (1999) Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metab Dispos 27:1350-1359.
    • (1999) Drug Metab Dispos , vol.27 , pp. 1350-1359
    • Obach, R.1
  • 20
    • 0000732256 scopus 로고
    • Autocatalytic inactivation of cytochrome P-450 and chloroperoxidase by l-aminobenzotriazole and other aryne precursors
    • Ortiz de Montellano PR, Mathews JM, and Langry KC (1984) Autocatalytic inactivation of cytochrome P-450 and chloroperoxidase by l-aminobenzotriazole and other aryne precursors. Tetrahedron 40:511-519.
    • (1984) Tetrahedron , vol.40 , pp. 511-519
    • Ortiz de Montellano, P.R.1    Mathews, J.M.2    Langry, K.C.3
  • 21
    • 0028930879 scopus 로고
    • Characterization of flavin containing monooxygenase 5 (FMO5) cloned from human and guinea pig: Evidence that the unique catalytic properties of FMO5 are not confined to the rabbit orthologs
    • Overby LH, Buckpitt AR, Lawton MP, Atta-Asafo-Adjei E, Schulze J, and Philpot RM (1995) Characterization of flavin containing monooxygenase 5 (FMO5) cloned from human and guinea pig: evidence that the unique catalytic properties of FMO5 are not confined to the rabbit orthologs. Arch Biochem Biophys 317:275-284.
    • (1995) Arch Biochem Biophys , vol.317 , pp. 275-284
    • Overby, L.H.1    Buckpitt, A.R.2    Lawton, M.P.3    Atta-Asafo-Adjei, E.4    Schulze, J.5    Philpot, R.M.6
  • 22
    • 0030833164 scopus 로고    scopus 로고
    • Quantitation and kinetic properties of hepatic microsomal and recombinant flavin-containing monooxygenases 3 and 5 from humans
    • Overby LH, Carver GC, and Philpot RM (1997) Quantitation and kinetic properties of hepatic microsomal and recombinant flavin-containing monooxygenases 3 and 5 from humans. Chem Biol Interact 106:29-45.
    • (1997) Chem Biol Interact , vol.106 , pp. 29-45
    • Overby, L.H.1    Carver, G.C.2    Philpot, R.M.3
  • 23
    • 24944435434 scopus 로고    scopus 로고
    • Oxidation of tamoxifen by human flavin containing monooxygenases (FMO1) and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochrome P450 and hemoglobin
    • Parte P and Kupfer D (2005) Oxidation of tamoxifen by human flavin containing monooxygenases (FMO1) and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochrome P450 and hemoglobin. Drug Metab Dispos 33:1446-1452.
    • (2005) Drug Metab Dispos , vol.33 , pp. 1446-1452
    • Parte, P.1    Kupfer, D.2
  • 25
    • 0034035244 scopus 로고    scopus 로고
    • Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes
    • Rawden HC, Kokwaro GO, Ward SA, and Edwards G (2000) Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes. Br J Clin Pharmacol 49:313-322.
    • (2000) Br J Clin Pharmacol , vol.49 , pp. 313-322
    • Rawden, H.C.1    Kokwaro, G.O.2    Ward, S.A.3    Edwards, G.4
  • 26
    • 0028964520 scopus 로고
    • Prochiral sulfides as in vitro probes for multiple forms of the flavin-containing monooxygenase
    • Rettie AE, Meier GP, and Sadeque AJM (1995) Prochiral sulfides as in vitro probes for multiple forms of the flavin-containing monooxygenase. Chem Biol Interact 96:3-15.
    • (1995) Chem Biol Interact , vol.96 , pp. 3-15
    • Rettie, A.E.1    Meier, G.P.2    Sadeque, A.J.M.3
  • 28
    • 0033105118 scopus 로고    scopus 로고
    • Integrated cytochrome P450 reaction phenotyping attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes
    • Rodrigues AD (1999) Integrated cytochrome P450 reaction phenotyping attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol 57:465-480.
    • (1999) Biochem Pharmacol , vol.57 , pp. 465-480
    • Rodrigues, A.D.1
  • 29
    • 0034013033 scopus 로고    scopus 로고
    • Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450
    • Sai Y, Dai R, Yang TJ, Krausz KW, Gonzalez FJ, Gelboin HV, and Shou M (2000) Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450. Xenobiotica 30:327-343.
    • (2000) Xenobiotica , vol.30 , pp. 327-343
    • Sai, Y.1    Dai, R.2    Yang, T.J.3    Krausz, K.W.4    Gonzalez, F.J.5    Gelboin, H.V.6    Shou, M.7
  • 30
    • 0034531789 scopus 로고    scopus 로고
    • Benzydamine N-oxygenation as an index reaction reflecting FMO activity in human liver microsomes and impact of FMO3 polymorphisms on enzyme activity
    • Stormer E, Roots I, and Brockmoller J (2000) Benzydamine N-oxygenation as an index reaction reflecting FMO activity in human liver microsomes and impact of FMO3 polymorphisms on enzyme activity. Br J. Clin Pharmacol 50:553-561.
    • (2000) Br J. Clin Pharmacol , vol.50 , pp. 553-561
    • Stormer, E.1    Roots, I.2    Brockmoller, J.3
  • 31
    • 33645072205 scopus 로고    scopus 로고
    • Treatment for advanced tumors: Src reclaims center stage
    • Summy JM and Gallick GE (2006) Treatment for advanced tumors: Src reclaims center stage. Clin Cancer Res 12:1398-1401.
    • (2006) Clin Cancer Res , vol.12 , pp. 1398-1401
    • Summy, J.M.1    Gallick, G.E.2
  • 32
    • 33745063122 scopus 로고    scopus 로고
    • SRC inhibitors as potential therapeutic agents for human cancers
    • Trevino JG, Summy JM, and Gallick GE (2006) SRC inhibitors as potential therapeutic agents for human cancers. Mini Rev Med Chem 6:681-687.
    • (2006) Mini Rev Med Chem , vol.6 , pp. 681-687
    • Trevino, J.G.1    Summy, J.M.2    Gallick, G.E.3
  • 34
    • 2442690439 scopus 로고    scopus 로고
    • Validated assays for human cytochrome P450 activities
    • Walsky L and Obach S (2004) Validated assays for human cytochrome P450 activities. Drug Metab Dispos 32:647-660.
    • (2004) Drug Metab Dispos , vol.32 , pp. 647-660
    • Walsky, L.1    Obach, S.2
  • 35
    • 0033844080 scopus 로고    scopus 로고
    • Immunoquantitation of FMO1 in human liver, kidney and intestine
    • Yeung CK, Lang DH, Thummel KE, and Rettie AE (2000) Immunoquantitation of FMO1 in human liver, kidney and intestine. Drug Metab Dispos 28:1107-1111.
    • (2000) Drug Metab Dispos , vol.28 , pp. 1107-1111
    • Yeung, C.K.1    Lang, D.H.2    Thummel, K.E.3    Rettie, A.E.4
  • 36
    • 0025316330 scopus 로고
    • Flavin-containing monooxygenases: Enzymes adapted for multisubstrate specificity
    • Ziegler DM (1990) Flavin-containing monooxygenases: enzymes adapted for multisubstrate specificity. Trends Pharmacol Sci 11:321-324.
    • (1990) Trends Pharmacol Sci , vol.11 , pp. 321-324
    • Ziegler, D.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.