Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-450 2C8 and P-450 3A4 in human liver microsomes

Drug Metabolism and Disposition

Volumn 27, Issue 11, 1999, Pages 1260-1266

  Yamazaki, Hiroshi ^a   Shibata, Ayaka ^a   Suzuki, Mikie ^a   Nakajima, Miki ^a   Shimada, Noriaki ^b   Guengerich, F Peter ^c   Yokoi, Tsuyoshi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b DAIICHI PURE CHEMICALS CO LTD   (Japan)

^c VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDIABETIC AGENT; COMPLEMENTARY DNA; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; KETOCONAZOLE; TROGLITAZONE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DIABETES MELLITUS; DRUG METABOLISM; DRUG OXIDATION; ENZYME ACTIVITY; HUMAN; HUMAN CELL; LIVER METABOLISM; LIVER MICROSOME; PHARMACOKINETICS; PRIORITY JOURNAL;

ARYL HYDROCARBON HYDROXYLASES; CATALYSIS; CHROMANS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HUMANS; HYPOGLYCEMIC AGENTS; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; OXIDATION-REDUCTION; QUINONES; RECOMBINANT PROTEINS; STEROID 16-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES; THIAZOLES; THIAZOLIDINEDIONES;

EID: 0032725398     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Bort R, Ponsoda X, Jover R, Gomez-Lechon MJ and Castell JV (1999) Diclofenac toxicity to hepatocytes: A role for drug metabolism in cell toxicity. J Pharmacol Exp Ther 288:65-72.
2. Brian WR, Srivastava PK, Umbenhauer DR, Lloyd RS and Guengerich FP (1989) Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in Saccharomyces cerevisiae. Biochemistry 28:4993-4999.
3. Fu Y, She C, Fujita T and Foote CS (1996) Photooxidation of troglitazone, a new antidiabetic drug. Photochem Photobiol 63:615-620.
4. Gillam E, Baba T, Kim B-R, Ohmori S and Guengerich FP (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch Biochem Biophys 305:123-131.
5. Gonzalez FJ and Gelboin HV (1994) Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metab Rev 26:165-183.
6. Guengerich FP (1994) Analysis and characterization of enzymes, in Principles and Methods of Toxicology (Hayes AW ed) pp 1259-1313, Raven Press, New York.
7. Guengerich FP (1995) Human cytochrome P450 enzymes, in Cytochrome P450 (Oritiz de Montellano PR ed) pp 473-535, Plenum Press, New York.
8. Guengerich FP and Shimada T (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 4:391-407.
9. 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.
10. Guengerich FP, Wang P and Mason PS (1981) Immunological comparison of rat, rabbit, and human liver NADPH-cytochrome P-450 reductase. Biochemistry 20:2379-2385.
11. Inoue K, Yamazaki H, Imiya K, Akasaka S, Guengerich FP and Shimada T (1997) Relationship between CYP2C9 and 2C19 genotypes and tolbutamide methyl hydroxylation and S-mephenytoin 4′-hydroxylation activities in livers of Japanese and Caucasian populations. Pharmacogenetics 7:103-113.
12. Izumi T, Enomoto S, Hoshiyama K, Sasahara K and Sugiyama Y (1997a) Pharmacokinetic stereoselectivity of troglitazone, an antidiabetic agent, in the KK mouse. Biopharm Drug Dispos 18:305-324.
13. Izumi T, Hoshiyama K, Enomoto S, Sasahara K and Sugiyama Y (1997b) Pharmacokinetics of troglitazone, an antidiabetic agent: Prediction of in vivo stereoselective sulfation and glucuronidation from in vitro data. J Pharmacol Exp Ther 280:1392-1400.
14. Jeppesen U, Gram LF, Vistisen K, Loft S, Poulsen HE and Brøsen K (1996) Dose-dependent inhibition of CYP1A2, CYP2C19, and CYP2D6 by citalopram, fluoxetine, fluvoxamine and paroxetine. Eur J Clin Pharmacol 51:73-78.
15. Kaplan B, Friedman G, Jacobs M, Viscuso R, Lyman N, DeFranco P, Bonomini L and Mulgaonkar SP (1998) Potential interaction of troglitazone and cyclosporine. Transplantation 65:1399-1400.
16. Kawai K, Kawasaki-Tokui Y, Odaka T, Tsuruta F, Kazui M, Iwabuchi H, Nakamura T, Kinoshita T, Ikeda T, Yoshioka T, Komai T and Nakamura K (1997) Disposition and metabolism of the new oral antidiabetic drug troglitazone in rats, mice and dogs. Arzneim-Forsch 47:356-368.
17. Kawai K, Odala T, Tsuruta F, Tokui T, Ikeda T and Nakamura K (1998) Stereoselective metabolism of new oral anti-diabetic agent troglitazone stereoisomers in liver. Xenobio Metab Dispos 13:362-368.
18. Koup JR, Anderson GD and Loi CM (1998) Effect of troglitazone on urinary excretion of 6β-hydroxycortisol. J Clin Pharmacol 38:815-818.
19. Kuramoto K, Shimizu N and Toda G (1998) Liver dysfunction associated with troglitazone (Noscal®). Rinsho-Iyaku 14:461-466.
20. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
21. Mancy A, Dijols S, Poli S, Guengerich FP and Mansuy D (1996) Interaction of sulfaphenazole derivatives with human liver cytochromes P450 2C: Molecular origin of the specific inhibitory effects of sulfaphenazole on CYP2C9 and consequences for the substrate binding site topology of CYP2C9. Biochemistry 35:16205-16212.
22. Odaka T, Kawai K, Tsuruta F, Ikeda T. Kinoshita T, Nakamura K, Shimada M and Yamazoe Y (1995) Pharmacokinetics of troglitazone (CS-045), a new oral antidiabetic drug: Phase I and phase II metabolism in female rats. Xenobio Metab Dispos 10 (Suppl): S386.
23. 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.
24. Otton SV, Kalow W and Seeman P (1984) High affinity of quinidine for a stereoselective microsomal binding site as determined by a radioreceptor assay. Experientia 40:973-974.
25. Parikh A, Gillam EMJ and Guengerich FP (1997) Bacterial catalysis of reactions important in mammalian drug and xenobiotic metabolism: Functional co-expression of six human microsomal cytochrome P450 enzymes with NADPH-cytochrome P450 reductase in Escherichia coli. Nat Biotechnol 15:784-788.
26. Physicians' Desk Reference (1999) Rezulin™, in Physicians' Desk Reference, 53rd ed., pp 2310-2314, Medical Economics Company, Inc., Montvale, NJ.
27. Pumford NR and Halmes NC (1997) Protein targets of xenobiotic reactive intermediates. Annu Rev Pharmacol Toxicol 37:91-117.
28. Rahman A, Korzekwa KR, Grogan J, Gonzalez FJ and Harris JW (1994) Selective biotransformation of taxol to 6α-hydroxytaxol by human cytochrome P450 2C8. Cancer Res 54:5543-5546.
29. 5. Arch Biochem Biophys 348:107-115.
30. Shimada T, Misono KS and Guengerich FP (1986) Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction. J Biol Chem 261:909-921.
31. Shimada T and Yamazaki H (1998) Cytochrome P450 reconstitution systems, in Methods in Molecular Biology (Phillips IR and Shephard EA eds) pp 85-93, Humana Press, Totowa, NJ.
32. 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.
33. Sparano N and Seaton TL (1998) Troglitazone in type II diabetes mellitus. Pharmacotherapy 18:539-548.
34. Summary Basis for Approvals (1997) Summary Basis for Approvals, no. 9, Troglitazone. The Society of Japanese Pharmacopoeia, Tokyo.
35. Walle T (1996) Assays of CYP2C8-and CYP3A4-mediated metabolism of taxol in vivo and in vitro. Methods Enzymol 272:145-151.
36. Watkins PB and Whitcomb RW (1998) Hepatic dysfunction associated with troglitazone. N Engl J Med 338:916-917.
37. Wrighton SA and Stevens JC (1992) The human hepatic cytochtomes P450 involved in drug metabolism. Crit Rev Toxicol 22:1-21.
38. Yamazaki H, Inoue K, Shaw PM, Checovich WJ, Guengerich FP and Shimada T (1997) 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.
39. Yamazaki H, Shaw PM, Guengerich FP and Shimada T (1998) Roles of cytochrome P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes. Chem Res Toxicol 11:659-665.
40. Yamazaki H, Ueng Y-F, Shimada T and Guengerich FP (1995) Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxin, and oxygen surrogates. Biochemistry 34:8380-8389.