메뉴 건너뛰기




Volumn 329, Issue 3, 2009, Pages 938-944

CYP2C9 amino acid residues influencing phenytoin turnover and metabolite regio- and stereochemistry

Author keywords

[No Author keywords available]

Indexed keywords

5 (4 HYDROXYPHENYL) 5 PHENYLHYDANTOIN; CYTOCHROME P450 2C9; FLURBIPROFEN; PHENYTOIN; WARFARIN;

EID: 66749089988     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.109.150706     Document Type: Article
Times cited : (20)

References (26)
  • 2
    • 0030454133 scopus 로고    scopus 로고
    • Roles of cytochrome P4502C9 and cytochrome P4502C19 in the stereoselective metabolism of phenytoin to its major metabolite
    • Bajpai M, Roskos LK, Shen DD, and Levy RH (1996) Roles of cytochrome P4502C9 and cytochrome P4502C19 in the stereoselective metabolism of phenytoin to its major metabolite. Drug Metab Dispos 24:1401-1403. (Pubitemid 26427180)
    • (1996) Drug Metabolism and Disposition , vol.24 , Issue.12 , pp. 1401-1403
    • Bajpai, M.1    Roskos, L.K.2    Shen, D.D.3    Levy, R.H.4
  • 3
    • 0020787408 scopus 로고
    • A sensitive and specific stable isotope assay for warfarin and its metabolites
    • Bush ED, Low LK, and Trager WF (1983) A sensitive and specific stable isotope assay for warfarin and its metabolites. Biomed Mass Spectrom 10:395-398.
    • (1983) Biomed Mass Spectrom , vol.10 , pp. 395-398
    • Bush, E.D.1    Low, L.K.2    Trager, W.F.3
  • 4
    • 0038691507 scopus 로고    scopus 로고
    • Rabbit CYP4B1 engineered for high-level expression in Escherichia coli: Ligand stabilization and processing of the N-terminus and heme prosthetic group
    • DOI 10.1016/S0003-9861(03)00278-9
    • Cheesman MJ, Baer BR, Zheng YM, Gillam EM, and Rettie AE (2003) Rabbit CYP4B1 engineered for high-level expression in Escherichia coli: ligand stabilization and processing of the N-terminus and heme prosthetic group. Arch Biochem Biophys 416:17-24. (Pubitemid 36818845)
    • (2003) Archives of Biochemistry and Biophysics , vol.416 , Issue.1 , pp. 17-24
    • Cheesman, M.J.1    Baer, B.R.2    Zheng, Y.-M.3    Gillam, E.M.J.4    Rettie, A.E.5
  • 5
    • 1842428730 scopus 로고    scopus 로고
    • Differential Roles of Arg97, Asp293, and Arg108 in Enzyme Stability and Substrate Specificity of CYP2C9
    • DOI 10.1124/mol.65.4.842
    • Dickmann LJ, Locuson CW, Jones JP, and Rettie AE (2004) Differential roles of Arg97, Asp293, and Arg108 in enzyme stability and substrate specificity of CYP2C9. Mol Pharmacol 65:842-850. (Pubitemid 38420489)
    • (2004) Molecular Pharmacology , vol.65 , Issue.4 , pp. 842-850
    • Dickmann, L.J.1    Locuson, C.W.2    Jones, J.P.3    Rettie, A.E.4
  • 6
    • 0035028935 scopus 로고    scopus 로고
    • Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: Inhibition by sulfaphenazole, omeprazole, and ticlopidine
    • DOI 10.1007/s002280100268
    • Giancarlo GM, Venkatakrishnan K, Granda BW, von Moltke LL, and Greenblatt DJ (2001) Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: Inhibition by sulfaphenazole, omeprazole, and ticlopidine. Eur J Clin Pharmacol 57:31-36. (Pubitemid 32391409)
    • (2001) European Journal of Clinical Pharmacology , vol.57 , Issue.1 , pp. 31-36
    • Giancarlo, G.M.1    Venkatakrishnan, K.2    Granda, B.W.3    Von Moltke, L.L.4    Greenblatt, D.J.5
  • 7
    • 0026542989 scopus 로고
    • Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences
    • Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 267:83-90.
    • (1992) J Biol Chem , vol.267 , pp. 83-90
    • Gotoh, O.1
  • 8
    • 0033574258 scopus 로고    scopus 로고
    • Enzymatic determinants of the substrate specificity of CYP2C9: Role of B'-C loop residues in providing the π-stacking anchor site for warfarin binding
    • Haining RL, Jones JP, Henne KR, Fisher MB, Koop DR, Trager WF, and Rettie AE (1999) Enzymatic determinants of the substrate specificity of CYP2C9: role of B'-C loop residues in providing the -stacking anchor site for warfarin binding. Biochemistry 38:3285-3292. (Pubitemid 129501388)
    • (1999) Biochemistry , vol.38 , Issue.11 , pp. 3285-3292
    • Haining, R.L.1    Jones, J.P.2    Henne, K.R.3    Fisher, M.B.4    Koop, D.R.5    Trager, W.F.6    Rettie, A.E.7
  • 9
    • 0035889154 scopus 로고    scopus 로고
    • Genetic polymorphism in exon 4 of cytochrome P450 CYP2C9 may be associated with warfarin sensitivity in Chinese patients
    • Leung AY, Chow HC, Kwong YL, Lie AK, Fung AT, Chow WH, Yip AS, and Liang R (2001) Genetic polymorphism in exon 4 of cytochrome P450 CYP2C9 may be associated with warfarin sensitivity in Chinese patients. Blood 98:2584-2587.
    • (2001) Blood , vol.98 , pp. 2584-2587
    • Leung, A.Y.1    Chow, H.C.2    Kwong, Y.L.3    Lie, A.K.4    Fung, A.T.5    Chow, W.H.6    Yip, A.S.7    Liang, R.8
  • 10
    • 13444292821 scopus 로고    scopus 로고
    • Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner
    • DOI 10.1124/dmd.104.001438
    • Liu KH, Kim MJ, Jung WM, Kang W, Cha IJ, and Shin JG (2005) Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner. Drug Metab Dispos 33:209-213. (Pubitemid 40216587)
    • (2005) Drug Metabolism and Disposition , vol.33 , Issue.2 , pp. 209-213
    • Liu, K.-H.1    Kim, M.-J.2    Jung, W.M.3    Kang, W.4    Cha, I.-J.5    Shin, J.-G.6
  • 11
    • 0002488006 scopus 로고    scopus 로고
    • Anticonvulsants
    • Levy RH, Thummel KE, Trager WF, Hansten PD, and Eichelbaum M eds Lippincott Williams & Wilkins, Philadelphia, PA
    • Mather GG and Levy RH (2000) Anticonvulsants, in Metabolic Drug Interactions (Levy RH, Thummel KE, Trager WF, Hansten PD, and Eichelbaum M eds) pp 217-232, Lippincott Williams & Wilkins, Philadelphia, PA.
    • (2000) Metabolic Drug Interactions , pp. 217-232
    • Mather, G.G.1    Levy, R.H.2
  • 12
    • 0037228099 scopus 로고    scopus 로고
    • Substrate selectivity of human cytochrome P450 2C9: Importance of residues 476, 365, and 114 in recognition of diclofenac and sulfaphenazole and in mechanism-based inactivation by tienilic acid
    • DOI 10.1016/S0003-9861(02)00548-9, PII S0003986102005489
    • Melet A, Assrir N, Jean P, Pilar Lopez-Garcia M, Marques-Soares C, Jaouen M, Dansette PM, Sari MA, and Mansuy D (2003) Substrate selectivity of human cytochrome P450 2C9: Importance of residues 476, 365, and 114 in recognition of diclofenac and sulfaphenazole and in mechanism-based inactivation by tienilic acid. Arch Biochem Biophys 409:80-91. (Pubitemid 36042904)
    • (2003) Archives of Biochemistry and Biophysics , vol.409 , Issue.1 , pp. 80-91
    • Melet, A.1    Assrir, N.2    Jean, P.3    Lopez-Garcia, M.P.4    Marques-Soares, C.5    Jaouen, M.6    Dansette, P.M.7    Sari, M.-A.8    Mansuy, D.9
  • 13
    • 0021361472 scopus 로고
    • Sodium diphenyl hydantoinate in the treatment of convulsive disorders
    • DOI 10.1001/jama.251.8.1062
    • Merritt HH and Putnam TJ (1938) Sodium diphenyl hydantoinate in the treatment of convulsive disorders. JAMA 111:1062-1067. (Pubitemid 14190701)
    • (1984) Journal of the American Medical Association , vol.251 , Issue.8 , pp. 1062-1067
    • Merritt, H.H.1    Putnam, T.J.2
  • 14
    • 55849096976 scopus 로고    scopus 로고
    • Functional analysis of phenylalanine residues in the active site of CYP2C9
    • Mosher CM, Hummel MA, Tracy TS, and Rettie AE (2008) Functional analysis of phenylalanine residues in the active site of CYP2C9. Biochemistry 47:11725-11734.
    • (2008) Biochemistry , vol.47 , pp. 11725-11734
    • Mosher, C.M.1    Hummel, M.A.2    Tracy, T.S.3    Rettie, A.E.4
  • 15
    • 0029944181 scopus 로고    scopus 로고
    • Structural flexibility and functional versatility of mammalian P450 enzymes
    • Negishi M, Uno T, Darden TA, Sueyoshi T, and Pedersen LG (1996) Structural flexibility and functional versatility of mammalian P450 enzymes. FASEB J 10:683-689. (Pubitemid 26172814)
    • (1996) FASEB Journal , vol.10 , Issue.7 , pp. 683-689
    • Negishi, M.1    Uno, T.2    Darden, T.A.3    Sueyoshi, T.4    Pedersen, L.G.5
  • 16
    • 0033065223 scopus 로고    scopus 로고
    • A common genetic basis for idiosyncratic toxicity of warfarin and phenytoin
    • DOI 10.1016/S0920-1211(99)00017-0, PII S0920121199000170
    • Rettie AE, Haining RL, Bajpai M, and Levy RH (1999) A common genetic basis for idiosyncratic toxicity of warfarin and phenytoin. Epilepsy Res 35:253-255. (Pubitemid 29298118)
    • (1999) Epilepsy Research , vol.35 , Issue.3 , pp. 253-255
    • Rettie, A.E.1    Haining, R.L.2    Bajpai, M.3    Levy, R.H.4
  • 19
    • 1442287104 scopus 로고    scopus 로고
    • Cost-effectiveness of Oral Phenytoin, Intravenous Phenytoin, and Intravenous Fosphenytoin in the Emergency Department
    • DOI 10.1016/j.annemergmed.2003.10.011
    • Rudis MI, Touchette DR, Swadron SP, Chiu AP, and Orlinsky M (2004) Cost-effectiveness of oral phenytoin, intravenous phenytoin, and intravenous fosphenytoin in the emergency department. Ann Emerg Med 43:386-397. (Pubitemid 38282651)
    • (2004) Annals of Emergency Medicine , vol.43 , Issue.3 , pp. 386-397
    • Rudis, M.I.1    Touchette, D.R.2    Swadron, S.P.3    Chiu, A.P.4    Orlinsky, M.5
  • 21
    • 0036206152 scopus 로고    scopus 로고
    • Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: Effect on atypical kinetic metabolism profiles
    • DOI 10.1124/dmd.30.4.385
    • Tracy TS, Hutzler JM, Haining RL, Rettie AE, Hummel MA, and Dickmann LJ (2002) Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: Effect on atypical kinetic metabolism profiles. Drug Metab Dispos 30:385-390. (Pubitemid 34263822)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.4 , pp. 385-390
    • Tracy, T.S.1    Matthew Hutzler, J.2    Haining, R.L.3    Rettie, A.E.4    Hummel, M.A.5    Dickmann, L.J.6
  • 22
    • 0030969352 scopus 로고    scopus 로고
    • Reciprocal size-effect relationship of the key residues in determining regio- And stereospecificities of DHEA hydroxylase activity in P450 2a5
    • DOI 10.1021/bi962654j
    • Uno T, Mitchell E, Aida K, Lambert MH, Darden TA, Pedersen LG, and Negishi M (1997) Reciprocal size-effect relationship of the key residues in determining regio-and stereospecificities of dhea hydroxylase activity in P450 2A5. Biochemistry 36:3193-3198. (Pubitemid 27142391)
    • (1997) Biochemistry , vol.36 , Issue.11 , pp. 3193-3198
    • Uno, T.1    Mitchell, E.2    Aida, K.3    Lambert, M.H.4    Darden, T.A.5    Pedersen, L.G.6    Negishi, M.7
  • 25
    • 0042265520 scopus 로고    scopus 로고
    • Crystal structure of human cytochrome P450 2C9 with bound warfarin
    • DOI 10.1038/nature01862
    • Williams PA, Cosme J, Ward A, Angove HC, Matak Vinkoviæ D, and Jhoti H (2003) Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature 424:464-468. (Pubitemid 36917499)
    • (2003) Nature , vol.424 , Issue.6947 , pp. 464-468
    • Williams, P.A.1    Cosme, J.2    Ward, A.3    Angove, H.C.4    Vinkovic, D.M.5    Jhoti, H.6
  • 26
    • 0037100519 scopus 로고    scopus 로고
    • Leu208Val and ILe181Leu variants of cytochrome P450 CYP2C9 are not related to the acenocoumarol dose requirement in a Spanish population [3]
    • DOI 10.1182/blood-2002-03-0821
    • Zarza J, Hermida J, Montes R, Alberca I, López ML, and Rocha E (2002) Leu208Val and Ile181Leu variants of cytochrome P450 CYP2C9 are not related to the acenocoumarol dose requirement in a Spanish population. Blood 100:734. (Pubitemid 34761151)
    • (2002) Blood , vol.100 , Issue.2 , pp. 734
    • Zarza, J.1    Hermida, J.2    Montes, R.3    Alberca, I.4    Lopez, M.L.5    Rocha, E.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.