Prediction of human liver microsomal oxidations of 7-ethoxycoumarin and chlorzoxazone with kinetic parameters of recombinant cytochrome P-450 enzymes

Drug Metabolism and Disposition

Volumn 27, Issue 11, 1999, Pages 1274-1280

  Shimada, Tsutomu ^a   Tsumura, Fujiko ^a   Yamazaki, Hiroshi ^a,b  

^a OSAKA PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXYCOUMARIN; CHLORZOXAZONE; COMPLEMENTARY DNA; CYTOCHROME P450; XENOBIOTIC AGENT;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; KINETICS; LIVER MICROSOME; OXIDATION; PREDICTION; PRIORITY JOURNAL;

CHLORZOXAZONE; COUMARINS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; ISOENZYMES; MICROSOMES, LIVER; OXIDATION-REDUCTION; RECOMBINANT PROTEINS;

TRICHOPLUSIA NI;

EID: 0032734466     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. Andersson T, Miners JO, Veronese ME, Tassaneeyakul W, Meyer UA and Birkett DJ (1993) Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism. Br J Clin Pharmacol 36:521-530.
2. Berthou F, Goasduff T, Lucas D, Dreano Y and Bot M-HL (1995) Interaction between two probes used for phenotyping cytochromes P4501A2 (caffeine) and P4502E1 (chlorzoxazone) in humans. Pharmacogenetics 5:72-79.
3. Carriere V. Goasduff T, Ratanasavanh D, Morel F, Gautier JC, Beaune P and Berthou F (1993) Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chem Res Toxicol 6:852-857.
4. Own L and Yang CS (1996) Effects of cytochrome P450 2E1 modulators on the pharmacokinetics of chlorzoxazone and 6-hydroxychlorzoxazone in rats. Life Sci 58:1575-1585.
5. Chiba K, Kobayashi K, Manabe K, Tani M, Kamataki T and Ishizaki T (1993) Oxidative metabolism of omeprazole in human liver microsomes: Cosegregation with S-mephenytoin 4′-hydroxylation. J Pharmacol Exp Ther 266:52-59.
6. Code EL, Crespi CL, Penman BW, Gonzalez FJ, Chang TK and Waxman DJ (1997) Human cytochrome P4502B6: Interindividual hepatic expression, substrate specificity, and role in procarcinogen activation. Drug Metab Dispos 25:985-993.
7. Crespi CL (1995) Xenobiotic-metabolizing human cells as tools for pharmacological and toxicological research. Adv Drug Res 26:179-235.
8. Crespi CL and Penman BW (1997) Use of cDNA-expressed human cytochrome P450 enzymes to study potential drug-drug interactions. Adv Pharmacol 43:171-188.
9. Crewe HK, Ellis SW, Lennard MS and Tucker GT (1997) Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes. Biochem Pharmacol 53:171-178.
10. Ekins S, Vandenbranden M, Ring BJ, Gillespie JS, Yang TJ, Gelboin HV and Wrighton SA (1998) Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther 286:1253-1259.
11. Engel G, Hofmann U, Heidemann H, Cosme J and Eichelbaum M (1996) Antipyrine as a probe for human oxidative drug metabolism: Identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther 59:613-623.
12. Gonzalez FJ (1990) Molecular genetics of the P-450 superfamily. Pharmacol Ther 45:1-38.
13. Gorski JC, Jones DR, Wrighton SA and Hall SD (1997) Contribution of duman CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 27:243-256.
14. Guengerich FP (1994) Analysis and characterization of enzymes, in Principles and Methods of Toxicology (Hayes AW ed) pp 1259-1313, Raven Press, New York.
15. Guengerich FP (1995) Human cytochrome P450 enzymes, in Cytochrome P450 (Oritiz de Montellano PR ed) pp 473-535, Plenum Press, New York.
16. Guengerich FP (1997) Role of cytochrome P450 enzymes in drug-drug interactions. Adv Pharmacol 43:7-35.
17. Guengerich FP and Shimada T (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 4:391-407.
18. Guengerich FP, Wang P and Davidson NK (1982) Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Biochemistry 21:1698-1706.
19. Hayes CL, Spink DC, Spink BC, Cao JQ, Walker NJ and Sutter TR (1996) 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1. Proc Natl Acad Sci USA 93:9776-9781.
20. Ito K, Iwatsubo T, Kanamitsu S, Nakajima Y and Sugiyama Y (1998) Quantitative prediction of in vivo drug clearance and drug interactions from in vitro data on metabolism, together with binding and transport. Anna Rev Pharmacol Toxicol 38:461-499.
21. Iwatsubo T, Hirota N, Ooie T, Suzuki H, Shimada N, Chiba K, Ishizaki T, Green CE, Tyson CA and Sugiyama Y (1997a) Prediction of in vivo drug metabolism in the human liver from in vitro metabolism data. Pharmacol Ther 73:147-171.
22. Iwatsubo T, Suzuki H, Shimada N, Chiba K, Ishizaki T, Green CE, Tyson CA, Yokoi T, Kamataki T and Sugiyama Y (1997b) Prediction of in vivo hepatic metabolic clearance of YM796 from in vitro data using human liver microsomes and recombinant P-450 isozymes. J Pharmacol Exp Ther 282:909-919.
23. Kawajiri K and Fujii-Kuriyama Y (1991) P450 and human cancer. Jpn J Cancer Res 82:1325-1335.
24. Kim RB, Yamazaki H, Chiba K, O'Shea D, Mimura M, Guengerich FP, Ishizaki T, Shimada T and Wilkinson GR (1996) In vivo and in vitro characterization of CYP2E1 activity in Japanese and Caucasians. J Pharmacol Exp Ther 279:4-11.
25. Lin JH and Lu AYH (1997) Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev 49:403-449.
26. Lowry OH, Rosebrough NJ, Fan AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
27. Mimura M, Baba T, Yamazaki H, Ohmori S, Inui Y, Gonzalez FJ, Guengerich FP and Shimada T (1993) Characterization of cytochrome P450 2B6 in human liver microsomes. Drug Metab Dispos 21:1048-1056.
28. m and V/K in enzyme kinetics. J Chem Educ 75:1153-1157.
29. O'Shea D, Davis SN, Kim RB and Wilkinson GR(1994) Effect of fasting and obesity in humans on the 6-hydroxylation of chlorzoxazone: A putative probe of CYP2E1 activity. Clin Pharmacol Ther 56:359-367.
30. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
31. Ono S, Hatanaka T, Hotta H, Tsutsui M, Satoh T and Gonzalez FJ (1995) Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics 5:143-150.
32. Ono S, Hatanaka T, Miyazawa S, Tsutsui M, Aoyama T, Gonzalez FJ and Satoh T (1996) Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: Role of CYP2B6, 2C19 and the 3A subfamily. Xenobiotica 26:1155-1166.
33. Patten CJ, Thomas PE, Guy RL, Lee M, Gonzalez FJ, Guengerich FP and Yang CS (1993) Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem Res Toxicol 6:511-518.
34. Pearce RE, Rodrigues AD, Goldstein JA and Parkinson A (1996) Identification of the human P450 enzymes involved in lansoprazole metabolism. J Phamacol Exp Ther 277:805-816.
35. Peter R, Böcker R, Beaune PH, Iwasaki M, Guengerich FP and Yang CS (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450 IIE1. Chem Res Toxicol 3:566-573.
36. Pichard L, Curi-Pedrosa R, Bonfils C, Jacqz-Aigrain E, Domergue J, Joyeux H, Cosme J, Guengerich FP and Maurel P (1995) Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Phamacol 47:410-418.
37. Raucy JL, Lasker JM, Lieber CS and Black M (1989) Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys 271:270-283.
38. Rendic S and DiCarlo FJ (1997) Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29:413-580.
39. 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.
40. Sharer JE and Wrighton SA (1996) Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos 24:487-494.
41. Shimada T, Hayes CL, Yamazaki H, Amin S, Hecht SS, Guengerich FP and Sutter TR (1996a) Activation of chemically diverse procarcinogens by human cytochrome P450 1B1. Cancer Res 56:2979-2984.
42. Shimada T, Yamazaki H, Foroozesh M, Hopkins NE, Alworth WL and Guengerich FP (1998) Selectivity of polycyclic inhibitors for human cytochromes P450 1A1, 1A2, and 1B1. Chem Res Toxicol 11:1048-1056.
43. Shimada T, Yamazaki H, Mimura M, Inui Y and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423.
44. Shimada T, Yamazaki H, Mimura M, Wakamiya N, Guengerich FP and Inui Y (1996b) Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs. Drug Metab Dispos 24:515-522.
45. Shimada T, Yun CH, Yamazaki H, Gautier JC, Beaune PH and Guengerich FP (1992) Characterization of human lung microsomal cytochrome P-450 1A1 and its role in the oxidation of chemical carcinogens. Mol Pharmacol 41:856-864.
46. Snawger JE, Roe AL, Benson RW, Casciano DA and Roberts DW (1994) Cytochrome P450-dependent metabolism of acetaminophen in four human transgenic lymphoblastoid cell lines. Pharmacogenetics 4:43-46.
47. Stresser DM and Kupfer D (1999) Monospecific antipeptide antibody to cytochrome P-450 2B6. Drug Metab Dispos 27:517-525.
48. Vesell ES, Seaton TDA and A-Rahim YI (1995) Studies on interindividual variations of CYP2E1 using chlorzoxazone as an in vivo probe. Pharmacogenetics 5:53-57.
49. Williams ML, Lennard MS, Martin IJ and Tucker GT (1994) Interindividuai variation in the isomerization of 4-hydroxytamoxifen by human liver microsomes: Involvement of cytochromes P450. Carcinogenesis 15:2733-2738.
50. Wiseman H and Lewis DFV (1996) 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 17:1357-1360.
51. Wrighton SA, Ring BJ and Vandenbranden M (1995) The use of in vitro metabolism techniques in the planning and interpretation of drug safety studies. Toxicol Pathol 23:199-208.
52. Yamazaki H, Guo Z and Guengerich FP (1995) Selectivity of cytochrome P450 2E1 in chlorzoxazone 6-hydroxylation. Drug Metab Dispos 23:438-440.
53. Yamazaki H, Guo Z, Persmark M, Mimura M, Inoue K, Guengerich FP and Shimada T (1994) Bufuralol hydroxylation by cytochrome P450 2D6 and 1A2 enzymes in human liver microsomes. Mol Pharmacol 46:568-577.
54. Yamazaki H, Inoue K, Mimura M, Oda Y, Guengerich FP and Shimada T (1996) 7-Ethoxycouroarin O-deethylation catalyzed by cytochromes P450 1A2 and 2E1 in human liver microsomes. Biochem Pharmacol 51:313-319.
55. Yamazaki H, Inoue K, Shaw PM, Checovich WJ, Guengerich FP and Shimada T (1997a) Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: Effects of contents of these two forms in individual human samples. J Pharmacol Exp Ther 283:434-442.
56. Yamazaki H, Inoue K, Turvy CG, Guengerich FP and Shimada T (1997b) Effects of freezing, thawing, and storage of human liver samples on the microsomal contents and activities of cytochrome P450 enzymes. Drug Metab Dispos 25:168-174.
57. Yamazaki H, Tanaka M and Shimada T (1999) Highly sensitive high-performance liquid chromatographic assay for coumarin 7-hydroxylation and 7-ethoxycoumarin O-deethylation by human liver cytochrome P450 enzymes. J Chromatogr B 721:13-19.
58. Yang TJ, Krausz KW, Sai Y, Gonzalez FJ and Gelboin HV (1999) Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramtne metabolism. Drug Metab Dispos 27:102-109.
59. Yang TJ, Shou M, Korzekwa KR, Gonzalez FJ, Gelboin HV and Yang SK (1998) Role of cDNA-expressed human cytochrornes P450 in the metabolism of diazepam. Biochem Pharmacol 55:889-896.