메뉴 건너뛰기




Volumn 14, Issue 11, 2014, Pages 1348-1355

Ritonavir analogues as a probe for deciphering the cytochrome P450 3A4 inhibitory mechanism

Author keywords

Crystal structure; CYP3A4; Inhibitor design; Ligand binding; Pharmacophore; Ritonavir analogues

Indexed keywords

ABT 538 DEAZA RITONAVIR; COBICISTAT; CYTOCHROME P450 3A4; CYTOCHROME P450 REDUCTASE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE; HYDROXYL GROUP; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RITONAVIR; THIAZOLE; UNCLASSIFIED DRUG; CYTOCHROME P450 3A; CYTOCHROME P450 3A INHIBITOR;

EID: 84903709977     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026614666140506120647     Document Type: Review
Times cited : (28)

References (22)
  • 1
    • 0032924934 scopus 로고    scopus 로고
    • Cytochrome P-450 3A4: Regulation and role in drug metabolism
    • Guengerich, F.P. Cytochrome P-450 3A4: regulation and role in drug metabolism. Annu. Rev. Pharmacol. Toxicol., 1999, 39, 1-17.
    • (1999) Annu. Rev. Pharmacol. Toxicol , vol.39 , pp. 1-17
    • Guengerich, F.P.1
  • 2
    • 84873620874 scopus 로고    scopus 로고
    • Understanding the mechanism of cytochrome P450 3A4: Recent advances and remaining problems
    • Sevrioukova, I.F.; Poulos, T.L. Understanding the mechanism of cytochrome P450 3A4: Recent advances and remaining problems. Dalton Trans., 2013, 42(9), 3116-3126.
    • (2013) Dalton Trans , vol.42 , Issue.9 , pp. 3116-3126
    • Sevrioukova, I.F.1    Poulos, T.L.2
  • 6
    • 0031790709 scopus 로고    scopus 로고
    • Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ri-tonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: Mechanism-based inactivation of cytochrome P4503A by ritonavir
    • Koudriakova, T.; Iatsimirskaia, E.; Utkin, I.; Gangl, E.; Vouros, P.; Storozhuk, E.; Orza, D.; Marinina, J.; Gerber, N. Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ri-tonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug. Metab. Dispos., 1998, 26(6), 552-561.
    • (1998) Drug. Metab. Dispos , vol.26 , Issue.6 , pp. 552-561
    • Koudriakova, T.1    Iatsimirskaia, E.2    Utkin, I.3    Gangl, E.4    Vouros, P.5    Storozhuk, E.6    Orza, D.7    Marinina, J.8    Gerber, N.9
  • 7
    • 0033948964 scopus 로고    scopus 로고
    • Potent mechanism-based inhibition of human CYP3A in vitro by am-prenavir and ritonavir: Comparison with ketoconazole
    • von Moltke, L.L.; Durol, A.L.; Duan, S.X.; Greenblatt, D.J. Potent mechanism-based inhibition of human CYP3A in vitro by am-prenavir and ritonavir: comparison with ketoconazole. Eur. J. Clin. Pharmacol., 2000, 56(3), 259-261.
    • (2000) Eur. J. Clin. Pharmacol , vol.56 , Issue.3 , pp. 259-261
    • von Moltke, L.L.1    Durol, A.L.2    Duan, S.X.3    Greenblatt, D.J.4
  • 8
    • 13244299150 scopus 로고    scopus 로고
    • Mechanism-based inac-tivation of CYP3A by HIV protease inhibitors
    • Ernest, C.S., 2nd; Hall, S. D.; Jones, D.R. Mechanism-based inac-tivation of CYP3A by HIV protease inhibitors. J. Pharmacol. Exp. Ther., 2005, 312(2), 583-591.
    • (2005) J. Pharmacol. Exp. Ther , vol.312 , Issue.2 , pp. 583-591
    • Ernest II, C.S.1    Hall, S.D.2    Jones, D.R.3
  • 9
    • 84884693033 scopus 로고    scopus 로고
    • The effect of ritonavir on human CYP2B6 catalytic activity: Heme modification contributes to the mechanism-based inactivation of CYP2B6 and CYP3A4 by ritonavir
    • Lin, H.L.; D'Agostino, J.; Kenaan, C.; Calinski, D.; Hollenberg, P.F. The effect of ritonavir on human CYP2B6 catalytic activity: heme modification contributes to the mechanism-based inactivation of CYP2B6 and CYP3A4 by ritonavir. Drug Metab. Dispos., 2013, 41(10), 1813-1824.
    • (2013) Drug Metab. Dispos , vol.41 , Issue.10 , pp. 1813-1824
    • Lin, H.L.1    D'Agostino, J.2    Kenaan, C.3    Calinski, D.4    Hollenberg, P.F.5
  • 10
    • 84055177551 scopus 로고    scopus 로고
    • Metabolomic screening and identification of the bioactivation pathways of ritonavir
    • Li, F.; Lu, J.; Ma, X. Metabolomic screening and identification of the bioactivation pathways of ritonavir. Chem. Res. Toxicol., 2011, 24(12), 2109-2114.
    • (2011) Chem. Res. Toxicol , vol.24 , Issue.12 , pp. 2109-2114
    • Li, F.1    Lu, J.2    Ma, X.3
  • 12
    • 73349103803 scopus 로고    scopus 로고
    • Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition
    • Sekiguchi, N.; Higashida, A.; Kato, M.; Nabuchi, Y.; Mitsui, T.; Takanashi, K.; Aso, Y.; Ishigai, M. Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition. Drug Metab. Phar-macokinet., 2009, 24(6), 500-510.
    • (2009) Drug Metab. Phar-macokinet , vol.24 , Issue.6 , pp. 500-510
    • Sekiguchi, N.1    Higashida, A.2    Kato, M.3    Nabuchi, Y.4    Mitsui, T.5    Takanashi, K.6    Aso, Y.7    Ishigai, M.8
  • 13
  • 14
    • 0030852009 scopus 로고    scopus 로고
    • Differential inhibition of cytochrome P450 isoforms by the protease inhibitors, ritonavir, saquinavir and indinavir
    • Eagling, V.A.; Back, D.J.; Barry, M.G. Differential inhibition of cytochrome P450 isoforms by the protease inhibitors, ritonavir, saquinavir and indinavir. Br. J. Clin. Pharmacol., 1997, 44(2), 190-194.
    • (1997) Br. J. Clin. Pharmacol , vol.44 , Issue.2 , pp. 190-194
    • Eagling, V.A.1    Back, D.J.2    Barry, M.G.3
  • 15
    • 0030430035 scopus 로고    scopus 로고
    • Cyto-chrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes
    • Kumar, G.N.; Rodrigues, A.D.; Buko, A.M.; Denissen, J.F. Cyto-chrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes. J. Pharmacol. Exp. Ther., 1996, 277(1), 423-431.
    • (1996) J. Pharmacol. Exp. Ther , vol.277 , Issue.1 , pp. 423-431
    • Kumar, G.N.1    Rodrigues, A.D.2    Buko, A.M.3    Denissen, J.F.4
  • 16
    • 0034177465 scopus 로고    scopus 로고
    • In vitro metabolism of trazodone by CYP3A: Inhibition by ketoconazole and human immunodeficiency viral protease inhibitors
    • Zalma, A.; von Moltke, L.L.; Granda, B.W.; Harmatz, J.S.; Shader, R.I.; Greenblatt, D.J. In vitro metabolism of trazodone by CYP3A: inhibition by ketoconazole and human immunodeficiency viral protease inhibitors. Biol. Psychiatry, 2000, 47(7), 655-661.
    • (2000) Biol. Psychiatry , vol.47 , Issue.7 , pp. 655-661
    • Zalma, A.1    von Moltke, L.L.2    Granda, B.W.3    Harmatz, J.S.4    Shader, R.I.5    Greenblatt, D.J.6
  • 17
    • 78649885201 scopus 로고    scopus 로고
    • Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir
    • Sevrioukova, I.F.; Poulos, T.L. Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir. Proc. Natl. Acad. Sci. U S A, 2010, 107(43), 18422-18427.
    • (2010) Proc. Natl. Acad. Sci. U S A , vol.107 , Issue.43 , pp. 18422-18427
    • Sevrioukova, I.F.1    Poulos, T.L.2
  • 18
    • 84859353403 scopus 로고    scopus 로고
    • Interaction of human cytochrome P4503A4 with ritonavir analogs
    • Sevrioukova, I.F.; Poulos, T.L. Interaction of human cytochrome P4503A4 with ritonavir analogs. Arch. Biochem. Biophys., 2012, 520(2), 108-116.
    • (2012) Arch. Biochem. Biophys , vol.520 , Issue.2 , pp. 108-116
    • Sevrioukova, I.F.1    Poulos, T.L.2
  • 19
    • 84877717752 scopus 로고    scopus 로고
    • Pyridine-substituted desoxyrito-navir is a more potent cytochrome P450 3A4 inhibitor than rito-navir
    • Sevrioukova, I.F.; Poulos, T.L. Pyridine-substituted desoxyrito-navir is a more potent cytochrome P450 3A4 inhibitor than rito-navir. J. Med. Chem., 2013, 56(9), 3733-3741.
    • (2013) J. Med. Chem , vol.56 , Issue.9 , pp. 3733-3741
    • Sevrioukova, I.F.1    Poulos, T.L.2
  • 20
    • 77149123315 scopus 로고    scopus 로고
    • Pharmacokinetics and phar-macodynamics of GS-9350: A novel pharmacokinetic enhancer without anti-HIV activity
    • Mathias, A.A.; German, P.; Murray, B.P.; Wei, L.; Jain, A.; West, S.; Warren, D.; Hui, J.; Kearney, B.P. Pharmacokinetics and phar-macodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin. Pharmacol. Ther., 2010, 87(10), 322-329.
    • (2010) Clin. Pharmacol. Ther , vol.87 , Issue.10 , pp. 322-329
    • Mathias, A.A.1    German, P.2    Murray, B.P.3    Wei, L.4    Jain, A.5    West, S.6    Warren, D.7    Hui, J.8    Kearney, B.P.9
  • 21
    • 84880150381 scopus 로고    scopus 로고
    • Dissecting cytochrome P450 3A4-ligand interactions using ritonavir analogues
    • Sevrioukova, I.F.; Poulos, T.L. Dissecting cytochrome P450 3A4-ligand interactions using ritonavir analogues. Biochemistry, 2013, 52(26), 4474-4481.
    • (2013) Biochemistry , vol.52 , Issue.26 , pp. 4474-4481
    • Sevrioukova, I.F.1    Poulos, T.L.2
  • 22
    • 69049094210 scopus 로고    scopus 로고
    • Synthesis and evaluation of inhibitors of cytochrome P450 3A (CYP3A) for pharmacokinetic enhancement of drugs
    • Flentge, C.A.; Randolph, J.T.; Huang, P.P.; Klein, L.L.; Marsh, K.C.; Harlan, J.E.; Kempf, D.J. Synthesis and evaluation of inhibitors of cytochrome P450 3A (CYP3A) for pharmacokinetic enhancement of drugs. Bioorg. Med. Chem. Lett., 2009, 19(18), 5444-5448.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , Issue.18 , pp. 5444-5448
    • Flentge, C.A.1    Randolph, J.T.2    Huang, P.P.3    Klein, L.L.4    Marsh, K.C.5    Harlan, J.E.6    Kempf, D.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.