Molecular modelling and quantitative structure-activity relationship studies on the interaction of omeprazole with cytochrome P450 isozymes

Toxicology

Volumn 125, Issue 1, 1998, Pages 31-44

  Lewis, David F V ^a   Lake, Brian G ^b  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b BIBRA INTERNATIONAL   (United Kingdom)

Author keywords

Molecular modelling; Omeprazole; QSAR

Indexed keywords

ANTIULCER AGENT; CYTOCHROME P450 ISOENZYME; OMEPRAZOLE;

ARTICLE; DNA POLYMORPHISM; DRUG METABOLISM; DRUG PROTEIN BINDING; ENZYME ACTIVE SITE; ENZYME SUBSTRATE COMPLEX; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SITE DIRECTED MUTAGENESIS;

ANTI-ULCER AGENTS; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; ISOENZYMES; LIVER; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; OMEPRAZOLE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032536171     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0300-483X(97)00159-5     Document Type: Article

References (58)

1. Andersson T. Omeprazole drug interaction studies. Clin. Pharm. 21:1991;195-212.
2. Andersson T., Miners J.O., Veronese M.E., Tassaneeyakul W., Tassaneeyakul W., Meyer U.A., Birkett D.J. Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism. Br. J. Clin. Pharmacol. 36:1993;521-530.
3. Ashby J. Consideration of CASE predictions of genotoxic carcinogenesis for omeprazole, methapyrilene and azathioprine. Mutat. Res. 272:1992;1-7.
4. Beresford A.P. CYPlA1: friend or foe? Drug Metab. Rev. 25:1993;503-517.
5. Birkett D.J., Andersson T., Miners J.O. Assays of omeprazole metabolism as a substrate probe for human CYP isoforms. Methods Enzymol. 272:1996;132-139.
6. Chenery R.J., Ayrton A., Oldham H.G., Norman S.J., Standring P. The interaction of omeprazole with rat liver cytochrome P450-mediated monoxygenase reactions in vitro and in vivo. Biochem. Pharmacol. 37:1988;1407-1414.
7. Chiba K., Kobayashi K., Manabe K., Tani M., Kamataki T., Ishizaki T. Oxidative metabolism of omeprazole in human liver microsomes: cosegregation with S-mephenytoin 4′-hydroxylation. J. Pharmacol. Exp. Ther. 266:1993;52-59.
8. Curi-Perosa R., Pichard L., Bonfils C., Jacqz-Aigrain E., Maurel P. Major implication of cytochrome P4503A4 in the oxidation metabolism of the antisecretory drugs omeprazole and lansoprazole in human liver microsomes and hepatocytes. Br. Clin. Pharmacol. 36:1993;156P.
9. Curi-Pedrosa R., Daujat M., Pichard L., Ourlin J.C., Clair P., Gervot L., Lesca P., Domergue J., Joyeuz H., Fourtanier G., Maurel P. Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J. Pharmacol. Exp. Ther. 269:1994;384-392.
10. Daujat M., Peryt B., Lesca P., Fourtanier G., Domergue J., Maurel P. Omeprazole an inducer of human CYPlA1 and 1A2 is not a ligand for the Ah receptor. Biochem. Biophys. Res. Commun. 188:1992;820-825.
11. Diaz D., Fabre I., Daujat M., Saint-Aubert B., Bories P., Michel H., Maurel P. Omeprazole is an aryl hydrocarbon-like inducer of human hepatic cytochrome P450. Gastroenterology. 99:1990;737-747.
12. Ekman L., Hausson E., Havu N., Carlsson E., Lundberg C. Toxicological studies on omeprazole. Scand. J. Gastroenterol. 20(Suppl. 108):1985;53-59.
13. Farrell G. P4501A2 and omeprazole. Gastroenterology. 102:1992;1822-1823.
14. Farrell G.C., Murray M. Human cytochrome P450 isoforms: their genetic heterogeneity and induction by omeprazole. Gastroenterology. 99:1990;885-889.
15. Furihata C., Hirose K., Matsushima T. Genotoxicity and cell proliferative activity of omeprazole in rat stomach mucosa. Mutat. Res. 262:1991;73-76.
16. Funck-Bretano C., Becquemont L., Lenevue A., Roux A., Jaillon P., Beaune P. Inhibition by omeprazole of proguanil metabolism: mechanism of the interaction in vitro and prediction of in vivo results from the in vitro experiments. J. Pharmacol. Exp. Ther. 280:1997;730-738.
17. Goldstein J.A., de Morais S.M.F. Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics. 4:1994;285-299.
18. Gonzalez F.J., Gelboin H.V. Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metab. Rev. 26:1994;165-183.
19. Guengerich F.P. Roles of cytochrome P450 enzymes in chemical carcinogenesis and cancer chemotherapy. Cancer Res. 48:1988;2946-2954.
20. Hsu M.-H., Griffm K.J., Wang Y., Kemper B., Johnson E.F. A single amino acid substitution congers progesterone 6β-hydroxylase activity to rabbit cytochrome P4502C3. J. Biol. Chem. 268:1993;6939-6944.
21. Humphries T.J. Clinical implications of drug interactions with the cytochrome P-450 enzyme system associated with omeprazole. Dig. Dis. Sci. 36:1991;1665-1669.
22. Ibeanu G.C., Ghanayem B.I., Linko P., Li L., Pedersen L.G., Goldstein J.A. Identification of residues 99, 220, and 221 of human cytochrome P4502C19 as key determinants of omeprazole hydroxylase activity. J. Biol. Chem. 271:1996;12496-12501.
23. Ioannides C., Parke D.V. Induction of cytochrome P4501 as an indicator of potential chemical carcinogenesis. Drug Metab. Rev. 25:1993;485-501.
24. Jensen J.C., Gugler R. Inhibition of human liver enzyme cytochrome P-450 by omeprazole. Br. J. Clin. Pharmacol. 21:1986;328-330.
25. Karam W.G., Goldstein J.A., Lasker J.M., Ghanayem B.I. Human CYP2C19 is a major omeprazole 5-hydroxylase, as demonstrated with recombinant cytochrome P450 enzymes. Drug Metab. Dispos. 24:1996;1081-1087.
26. Ko J.-W., Sukhova N., Thacker D., Chen P., Flockhart D.A. Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug. Metab. Dispos. 25:1997;853-862.
27. Krusekopf S., Kleeberg U., Hildebrandt A.G., Ruckpaul K. Effects of benzimidazole derivatives in cytochrome P450 lA1 expression in a human hepatoma cell line. Xenobiotica. 27:1997;1-9.
28. bm3). Xenobiotica. 25:1995;333-366.
29. Lewis, D.F.V., 1996. Cytochromes P450: Structure, Function and Mechanism. Taylor and Francis, London.
30. Lewis D.F.V. Quantitative structure-activity relationships in substrates, inducers and inhibitors of cytochrome P4501 (CYP1). Drug Metab. Rev. 29:1997;589-650.
31. Lewis D.F.V., Lake B.G. Molecular modelling of CYP1A subfamily members based on an alignment with CYP102: rationalization of CYP1A substrate specificity in terms of active site amino acid residues. Xenobiotica. 26:1996;723-753.
32. Lewis D.F.V., Eddershaw P.J., Goldfarb P.S., Tarbit M.H. Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica. 26:1996;1067-1086.
33. Lewis D.F.V., Eddershaw P.J., Goldfarb P.S., Tarbit M.H. Molecular modelling of cytochrome P4502D6 (CYP2D6) based on an alignment with CYP102: structural studies on specific CYP2D6 substrate metabolism. Xenobiotica. 27:1997;319-340.
34. Lewis, D.F.V., Dickins, M., Weaver, R.J., Eddershaw, P.J., Tarbit, M.H., Goldfarb, P.S., 1997. Molecular modelling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily. Xenobiotica (in press).
35. Lucier G.W., Thompson C.L., Hoel D.J. Omeprazole, cytochrome P450, and chemical carcinogenesis. Gastroenterology. 102:1992;1823-1824.
36. Mereto E., Ghia M., Martelli A., Brambilla G. Lack of evidence of omeprazole genotoxicity in Sprague-Dawley rats. Mutagenesis. 8:1993;379-386.
37. Miners, J.O., 1995. In vitro approaches for the prediction of oxidative drug metabolism in vivo. Proc. 4th Int. ISSX Meeting, Seattle, WA, August 27-31, 1995, p.2.
38. Murray M., Ryan A.J. The binding to oxidized cytochromes P450 and inhibition of mixed-function oxidases by aryl-substituted benzimidazoles and related compounds. Chem.-Biol. Interact. 43:1983;341-351.
39. Okudaira, K., Akiyama, T., Iiyama, Y., Nagasaka, Y., Chiba, K., Hayashi, M., 1995. Prediction of intrinsic clearance of omeprazole in humans: in vivo-in vitro correlation and interspecies scaling. Proc. 4th Int. ISSX Meeting, Seattle, WA, August 27-31, 1995, p.63.
40. Parkinson A., Hurwitz A. Omeprazole and the induction of human cytochrome P-450: a response to concerns about potential adverse effects. Gastroenterology. 100:1991;1157-1164.
41. Phillips D.H., Hewer A., Osborne M.R. Interaction of omeprazole with DNA in rat tissues. Mutagenesis. 7:1992;277-283.
42. Ravichandran K.G., Boddupalli S.S., Hasemann C.A., Peterson J.A., Deisenhofer J. Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450s. Science. 261:1993;731-736.
43. Rekker R.F., ter Laak A.M., Mannhold R. On the reliability of calculated log P values: Rekker, Hansch/Leo and Suzuki approach. Quant. Struc. Act. Relatsh. 12:1993;152-157.
44. Richardson T.H., Johnson E.F. Alterations of the regio-specificity of progesterone metabolism by the mutagenesis of two key amino acid residues in rabbit cytochrome P4502C3v. J. Biol. Chem. 269:1994;23937-23943.
45. Rosenkranz H.S., Klopman G. Omeprazole: an exploration of its reported genotoxicity. Mutagenesis. 6:1991;381-384.
46. Rost K.L., Roots I. Accelerated caffeine metabolism after omeprazole treatment is indicated by urinary metabolise ratios: coincidence with plasma clearance and breath test. Clin. Pharmacol. Ther. 55:1994;402-411.
47. 13C-[N-3-methy] caffeine breath test in poor and extensive metabolizers of S-mephenytoin. Clin. Pharmacol. Ther. 52:1992;170-180.
48. Rost K.L., Brösicke H., Heinmeyer G., Roots I. Specific and dose-dependent enzyme induction by omeprazole in human beings. Hepatology. 20:1994;1204-1212.
49. + ATPase. Ann. Rev. Pharmacol. Toxicol. 35:1995;277-305.
50. Sharp K.A., Nicholls A., Fine R.F., Honig B. Reconciling the magnitude of the microscopic and macroscopic hydrophobic effects. Science. 252:1991;106-109.
51. Shimada T., Iwasaki M., Martin M.V., Guengerich F.P. Human liver microsomal cytochrome P450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response to Salmonella tryphimurium TA 1535/pSK1002. Cancer Res. 49:1989;3218-3228.
52. Shimada T., Yamazaki H., Mimura M., Inui Y., Guengerich F.P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals. J. Pharmacol. Exp. Ther. 270:1994;414-423.
53. VandenBranden M., Ring B.J., Binkley S.N., Wrighton S.A. Interaction of human liver cytochromes P450 in vitro with LY307640, a gastric proton pump inhibitor. Pharmacogenetics. 6:1996;81-91.
54. Wedlund P.J., Wilkinson G.R. In vivo and in vitro measurement of CXYP2C19 activity. Methods Enzymol. 272:1996;105-114.
55. Williams D.H., Cox J.P.L., Doig A.J., Gardner M., Gerhard V., Kaye P.T., Lal A.R., Nicholls I.A., Salter C.J., Mitchell R.C. Toward the semiquantitative estimation of binding constants: guides for peptide-peptide binding in aqueous solution. J. Am. Chem. Soc. 113:1991;7020-7030.
56. Wiseman H., Lewis D.F.V. The metabolism of tamoxifen by human cytochromes P450 is rationalized by molecular modelling of the enzyme-substrate interactions: potential importance to its proposed anti-carcinogenic/carcinogenic actions. Carcinogenesis. 17:1996;1357-1360.
57. Zomorodi K., Houston J.B. Selectivity of omeprazole inhibition towards rat liver cytochromes P450. Xenobiotica. 27:1997;49-58.
58. Zomorodi K., Houston J.B. Diazepam-omeprazole inhibition interaction: an in vitro investigation using human liver microsomes. Br. J. Clin. Pharmacol. 42:1996;157-162.