Effect of ethanol on spectral binding, inhibition, and activity of CYP3A4 with an antiretroviral drug nelfinavir

Biochemical and Biophysical Research Communications

Volumn 402, Issue 1, 2010, Pages 163-167

  Kumar, Santosh ^a   Earla, Ravinder ^a   Jin, Mengyao ^a   Mitra, Ashim K ^a   Kumar, Anil ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

Alcohol; CYP3A4; Inhibition; Metabolism; Nelfinavir; Spectral binding

Indexed keywords

2 PROPANOL; ALCOHOL; CYTOCHROME P450 3A4; ISOBUTANOL; ISOPENTYL ALCOHOL; METHANOL; NELFINAVIR;

ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; CONCENTRATION RESPONSE; DRUG ALCOHOL INTERACTION; DRUG METABOLISM; DRUG PROTEIN BINDING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; IC 50; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL;

ALCOHOLISM; ANTI-RETROVIRAL AGENTS; BINDING SITES; CYTOCHROME P-450 CYP3A; ETHANOL; HIV INFECTIONS; HUMANS; LIVER; METABOLIC DETOXICATION, DRUG; NELFINAVIR; PROTEIN BINDING;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 78049311288     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2010.10.014     Document Type: Article

References (35)

1. Anzenbacher P., Anzenbacherová E. Cytochromes P450 and metabolism of xenobiotics. Cell Mol. Life Sci. 2001, 58:737-747.
2. Walubo A. The role of cytochrome P450 in anti-retroviral drug interactions. Expert Opin. Drug Toxicol. 2007, 3:583-598.
3. Granfors M.T., Wang J.S., Kajosaari L.I., Laitila J., Neuvonen P.J., Backman J.T. Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Clin. Pharmacol. Toxicol. 2006, 98:79-85.
4. Pal D., Mitra A.K. MDR- and CYP3A4-mediated drug-drug interactions. J. Neuroimmune Pharmacol. 2006, 1:323-339.
5. Xu L., Desai M.C. Pharmacokinetic enhancers for HIV drugs. Curr. Opin. Investig. Drugs 2009, 10:775-786.
6. Weathermon R., Crabb D.W. Alcohol and medication interactions. Alcohol Res. Health 1999, 23:40-54.
7. Fraser A.G. Pharmacokinetic interactions between alcohol and other drugs. Clin. Pharmacokinet. 1997, 33:79-90.
8. Asai H., Imaoka S., Kuroki T., Monna T., Funae Y. Microsomal ethanol oxidizing system activity by human hepatic cytochrome P450s. J. Pharmacol. Exp. Ther. 1996, 277:1004-1009.
9. Jin M., Arya P., Patel K., Singh B., Silverstein P., Bhat H., Kumar A., Kumar S. Effect of alcohol on drug efflux protein and drug metabolic enzymes in U937 macrophages. Alcohol Clin. Exp. Res. 2011, 35:1-8.
10. Gavegnano C., Schinazi R.F. Antiretroviral therapy in macrophages: implication for HIV eradication. Antivir. Chem. Chemother. 2009, 20:63-78.
11. Dwyer D.S., Bradley R.J. Chemical properties of alcohols and their protein binding sites. Cell Mol. Life Sci. 2000, 57:265-275.
12. Park H., Lee S., Suh J. Structural and dynamical basis of broad substrate specificity, catalytic mechanism, and inhibition of cytochrome P450 3A4. J. Am. Chem. Soc. 2005, 127:13634-13642.
13. Davydov D.R., Baas B.J., Sligar S.G., Halpert J.R. Allosteric mechanisms in cytochrome P450 3A4 studied by high-pressure spectroscopy: pivotal role of substrate-induced changes in the accessibility and degree of hydration of the heme pocket. Biochemistry 2007, 46:7852-7864.
14. De Clercq E. Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV. Int. J. Antimicrob. Agents 2009, 33:307-320.
15. Brüning A., Gingelmaier A., Friese K., Mylonas I. New prospects for nelfinavir in non-HIV-related diseases. Curr. Mol. Pharmacol. 2010, 3:91-97.
16. Domanski T.L., He Y.A., Khan K.K., Roussel F., Wang Q., Halpert J.R. Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity. Biochemistry 2001, 40:10150-10160.
17. Harlow G.R., Halpert J.R. Analysis of human cytochrome P450 3A4 cooperativity: construction and characterization of a site-directed mutant that displayes hyperbolic steroids hydroxylation kinetics. Proc. Natl. Acad. Sci. USA 1998, 95:6636-6641.
18. Talakad J.C., Kumar S., Halpert J.R. Decreased susceptibility of the cytochrome P450 2B6 variant K262R to inhibition by several clinically important drugs. Drug Metab. Dispos. 2009, 37:644-650.
19. Kumar S., Liu H., Halpert J.R. Engineering of cytochrome P450 3A4 for enhanced peroxide-mediated substrate oxidation using directed evolution and site-directed mutagenesis. Drug Metab. Dispos. 2006, 34:1958-1965.
20. Vuppugalla R., Chang S.Y., Zhang H., Marathe P.H., Rodrigues D.A. Effect of commonly used organic solvents on the kinetics of cytochrome P450 2B6- and 2C8-dependent activity in human liver microsomes. Drug Metab. Dispos. 2007, 35:1990-1995.
21. Nishiya Y., Nakamura K., Okudaira N., Abe K., Kobayashi N., Okazaki O. Effects of organic solvents on the time-dependent inhibition of CYP3A4 by diazepam. Xenobiotica 2010, 40:1-8.
22. Lillibridge J.H., Liang B.H., Kerr B.M., Webber S., Quart B., Shetty B.V., Lee C.A. Characterization of the selectivity and mechanism of human cytochrome P450 inhibition by the human immunodeficiency virus-protease inhibitor nelfinavir mesylate. Drug Metab. Dispos. 1998, 26:609-616.
23. T.M. Sandoval, H.M. Grettenberger, and K.E. Zhang, Metabolism of nelfinavir mesylate and HIV-1 protease inhibitor by human liver microsomes and recombinant human isoforms, XII Annual Meeting and Exposition of the American Association of Pharmaceutical Scientists; 1998, San Francisco. Abstract 1096. American Association of Pharmaceutical Scientists, Arlington, VA.
24. Wu E.Y., Sandoval T.M., Lee C.A., Zhang K., Liang B.H., Shetty B.V. In vitro metabolism studies with the HIV-1 protease inhibitor, Viracept (AG1343). ISSX Proc. 1996, 10:326.
25. Hirani V.N., Raucy J.L., Lasker J.M. Conversion of the HIV protease inhibitor nelfinavir to a bioactive metabolite by human liver CYP2C19. Drug Metab. Dispos. 2004, 32:1462-1467.
26. K.E. Zhang, E. Wu, A.K. Patick, B. Kerr, M. Zorbas, A. Lankford, T. Kobayashi, Y. Maeda, B. Shetty, S. Webber, Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities, Antimicrob. Agents Chemother. 45 (2001) 1086-1093. Erratum in: Antimicrob. Agents Chemother. 45 (2001) 2405.
27. Chiba M., Nshime J.A., Lin J.H. In vitro metabolism of indinavir in the human fetal liver microsomes. Drug Metab. Dispos. 1997, 25:1219-1222.
28. Koudriakova T., Iatsimirskaia E., Utkin I., Gangl E., Vouros P., Storozhuk E., Orza D., Marinina J., Gerbe N. Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug Metab. Dispos. 1998, 26:552-561.
29. Kumar G.N., Rodrigues A.D., Buko A.M., Denissen J.F. Cytochrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes. J. Pharmacol. Exp. Ther. 1996, 277:423-431.
30. Fitzsimmons M.E., Collins J.M. Selective biotransformation of the human immunodeficiency virus protease inhibitor saquinavir by human small-intestinal cytochrome P4503A4: potential contribution to high first-pass metabolism. Drug Metab. Dispos. 1997, 25:256-266.
31. Flexner C.W., Cargill V.A., Sinclair J., Kresina T.F., Cheever L. Alcohol use can result in enhanced drug metabolism in HIV pharmacotherapy. AIDS Patient Care STDS 2001, 15:57-58.
32. Miguez M.J., Shor-Posner G., Morales G., Rodriguez A., Burbano X. HIV treatment in drug abusers: impact of alcohol use. Addiction Biology, Blackwell Publishing Limited 2003, 8:33-37.
33. Shibata N., Kageyama M., Kimura K., Tadano J., Hukushima H., Namiki H., Yoshikawa Y., Takada K. Evaluation of factors to decrease plasma concentration of an HIV protease inhibitor, saquinavir in ethanol-treated rats. Biol. Pharm. Bull. 2004, 27:203-209.
34. Kresina T.F., Flexner C.W., Sinclair J., Correia M.A., Stapleton J.T., Adeniyi-Jones S. Alcohol Use and HIV Pharmacotherapy. AIDS Res. Hum. Retrovir. 2001, 18:757-770.
35. Kalichman S.C., Amaral C.M., White D., Swetsze C., Pope H., Kalichman M.O., Cherry C., Eaton L. Prevalence and clinical implications of interactive toxicity beliefs regarding mixing alcohol and antiretroviral therapies among people living with HIV/AIDS. AIDS Patient Care STDS 2009, 23:449-454.