Examination of metabolic pathways and identification of human liver cytochrome P450 isozymes responsible for the metabolism of barnidipine, a calcium channel blocker

Xenobiotica

Volumn 27, Issue 9, 1997, Pages 885-900

  Teramura, T ^a   Fukunaga, Y ^a   Van Hoogdalem, E J ^b   Watanabe, T ^a   Higuchi, S ^a  

^a ASTELLAS PHARMA INC   (Japan)

^b ADME   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMITRIPTYLINE; CALCIUM ANTAGONIST; CHLORZOXAZONE; CIMETIDINE; CYCLOSPORIN A; CYTOCHROME P450 ISOENZYME; DEXTROMETHORPHAN; DIAZEPAM; DICLOFENAC; DRUG METABOLITE; ERYTHROMYCIN; FELODIPINE; GLIBENCLAMIDE; KETOCONAZOLE; MEPIRODIPINE; MEVINOLIN; NITRENDIPINE; ORPHENADRINE; PHENYTOIN; QUINIDINE; SIMVASTATIN; SPARTEINE; SULFAPHENAZOLE; TESTOSTERONE; THEOPHYLLINE; TOLBUTAMIDE; TROLEANDOMYCIN; UNINDEXED DRUG; VERAPAMIL; WARFARIN;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ANALYSIS; HUMAN; HUMAN TISSUE; LIVER MICROSOME;

CALCIUM CHANNEL BLOCKERS; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; DRUG INTERACTIONS; ENZYME INHIBITORS; HUMANS; ISOENZYMES; LIVER; MASS SPECTROMETRY; MICROSOMES, LIVER; NADP; NIFEDIPINE;

EID: 0030770247     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982597240064     Document Type: Article

References (35)

1. AUGUSTO, O., BEILAN, H. and ORTIZ DE MONTELLANO, P., 1982, The catalytic mechanism of cytochrome P-450. Spin-trapping evidence for one-electron substrate oxidation. Journal of Biological Chemistry, 257, 11288-11295.
2. BÄÄRNHIELM, C. and HANSSON, G., 1986, Oxidation of 1,4-dihydropyridines by prostaglandin synthase and peroxidic function of cytochrome P-450. Demonstration of a free radical intermediate. Biochemical Pharmacology 35, 1419-1425.
3. BAILEY, D. G., ARNOLD, J. M. O., STRONG, H. A. and SPENCE, J. D., 1993, Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Clinical and Pharmacological Therapeutics, 54, 589-594.
4. BAILEY, D. G., MUNOZ, C., ARNOLD, J. M. O. and SPENCE, J. D., 1992, Grapefruit juice and naringin interaction with nitrendipine. Clinical Pharmacology and Therapeutics, 51, 156.
5. BAILEY, D. G., SPENCE, J. D., MUNOZ, C. and ARNOLD, J. M. O., 1991, Interaction of citrus juices with felodipine and nifedipine. Lancet 337, 268-269.
6. BÖCKER, R. H. and GUENGERICH, F. P., 1986, Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis (alkoxycarbonyl)-1,4-dihydropyndines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. Journal of Medical Chemistry, 29, 1596-1603.
7. EVENING, M. K., CHANG, R. L., HUANG, M. T., FORTNER, J. G., WOOD, A. W. and CONNEY, A. H., 1981, Activation and inhibition of benzo(a)pyrene and aflatoxin B-1 metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Research, 41, 67-72.
8. COPPACK, S. W., LANT, A. F., MCINTOSH, C. S. and RODGERS, A. V., 1990, Pharmacokinetic and pharmacodynamic studies of glibenclamide in non-insulin dependent diabetes mellitus. British Journal of Clinical Pharmacology, 29, 673-684.
9. GUENGERICH, F. P. and BÖCKER, R. H., 1988, Cytochrome P-450-catalyzed dehydrogenation of 1,4-dihydropyridines. Journal of Biological Chemistry, 263, 8168-8175.
10. GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P., KREMERS, H., WOLFE, P. T. and WAXMAN, D. J., 1986, Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 261, 5051-5060.
11. GUENGERICH, F. P., PETERSON, L. A. and BÖCKER, R. H., 1988, Cytochrome P-450-catalyzed hydroxylation and carboxylic acid ester cleavage of Hantzsch pyridine esters. Journal of Biological Chemistry 263, 8176-8183.
12. HA, H. R., CHEN, J., FREUBURGHAUS, A. U. and FOLLATH, F., 1995, Metabolism of theophylline by cDNA-expressed human cytochromes P-450. British Journal of Clinical Pharmacology 39, 321-326.
13. KANN, J., KROL, G. J., RAEMSCH, K. D., BURKHOLDER, D. E. and LEVITT, M. J., 1984, Bioequivalence and metabolism of nitrendipine administered orally to healthy volunteers. Journal of Cardiovascular Pharmacology, 6, S968-973.
14. KNODELL, R. G., BROUWNE, D. G., GWOZDZ, G. P., BRIAN, W. R. and GUENGERICH, F. P., 1991, Differential inhibition of individual human liver cytochromes P-450 by cimetidine, Gastroenterology, 101, 1680-1691.
15. KONDO, S., KIKUCHI, A., YAMAMOTO, K., AKIMOTO, K., TAKAHASHI, K., AWATA, N. and SUGIMOTO, I., 1980, Identification of nifedipine metabolites and their determination by gas chromatography. Chemical Pharmacological Bulletin, 28, 1-7.
16. KRONBACH, T., FISHER, V. and MEYER, U. A., 1988, Cyclosporin metabolism in human liver: identification of a cytochrome P450III gene family as the major cyclosporin metabolizing enzyme explains interactions of cyclosporin with other drugs. Clinical and Pharmacological Therapeutics, 43, 630-635.
17. KUHNAU, J., 1976, The flavonoids: a class of semi-essential food components. Their role in human nutrition. World Review of Nutrition and Dietetics, 24, 117-191.
18. LEEMANN, T., TRANSON, C. and DAYER, P., 1992, Cytochrome P450TB (CYP2C): a major monooxigenase catalyzing diclofenac 4′-hydroxylation in human liver. Life Sciences 52, 29-34.
19. MINISCALCO, A., LUNDÄHL, J., REGARDH, C. G., EDGAR, B. and ERIKSSON, U. G., 1992, Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. Journal of Pharmacology and Experimental Therapeutics, 261, 1195-1199.
20. PENG, H. M., RANER, G. M., VAZ., A. D. N. and COON, M. J., 1995, Oxidative cleavage of esters and amines to carbonyl products by cytochrome P450. Archives of Biochemistry and Biophysics, 318, 333-339.
21. PENTIKAINEN, P. J., SARAHEIMO, M., SCHWARTZ, J. I., AMIN, R. D., SCHWARTZ., M. S., BRUNNER-FERBER, K. and ROGERS, J. D., 1992, Comparative pharmacokinetics of lovastatin, simvastatin and pravastatin in humans. Journal of Clinical Pharmacology, 32, 136-140.
22. PICHARD, L., FABRE, I., FABRE, G., DOMERGUE, J., AUBERT, B. S., MOURAD, G. and MAUREL, P., 1990, Cyclosporin A drug interactions: screening for inducers and inhibitors of cytochrome P-450 (Cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metabolism and Disposition 18, 595-606.
23. PTACHCINSKI, R. J., VENKATARAMANAN, R. and BURUKART, G. J., 1986, Clinical pharmacokinetics of cyclosporin. Clinical Pharmacokinetics, 11, 107-132.
24. RETTIE, A. E., KORZETWA, K. R., KUNTZE, K. L., LAWRENCE, R. F., EDDY, C. A., AOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J. and TRAGER, W. F. 1992, Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: a role for P4502C9 in the etiology of (S)-warfarin drug interactions. Chemical Research in Toxicology, 5, 54-59.
25. REYER-PFAFF, U., PFANDL, B., NILL, K., NUSSER, E., MONNEY, C., JONZIER-PEREY, M., BAETTIG, D. and BAUMANN, P., 1992, Enantioselective amitriptyline metabolism in patients phenotyped for two cytochrome P450 isozymes. Clinical Pharmacology and Therapeutics, 52, 350-358.
26. SOMOGYI, A. and MUIRHEAD, M., 1987, Pharmacokinetic interactions of cimetidine. Clinical Pharmacokinetics, 12, 321-366.
27. SPATZENEGGER, M. and JAEGER, W., 1995, Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metabolism Reviews, 27, 397-417.
28. STOPHER, D. A., BERESFORD, A. P., MACRAE, P. V. and HUMPHREY, M. J., 1988, The metabolism and pharmacokinetics of amlodipine in humans and animals. Journal of Cardiovascular Pharmacology, 12, S55-59.
29. TAMAZAWA, K., ARIMA, H., KAJIMA, T., ISOMURA, Y., OKADA, M., FUJITA, S., FURUYA, T., TAKENAKA, T., INAGAKI, O. and TERAI, M., 1986, Stereoselectivity of potent calcium antagonist, 1-benzyl-3-pyrrolidinyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. Journal of Medical Chemistry, 29, 2504-2511.
30. TERAMTRA, T., TOKUNAGA, T., MATSUMOTO, H., WATANABE, T. and HIGUCHI, S., 1996, Metabolism of barnidipine hydrochloride, a potent calcium antagonist, in rat and dog. Xenobiotica, 26, 177-187.
31. TERAMURA, T., WATANABE, T., HIGUCHI, S. and HASHIMOTO, K., 1995, Pharmacokinetics of barnidipine hydrochloride, a new calcium channel blocker, in the rat, dog and human. Xenobiotica, 25, 1237-1246.
32. TERAMURA, T., WATANABE, T., HIGUCHI, S. and HASHIMOTO, K., 1997, Metabolism and pharmacokinetics of barnidipine hydrochloride, a calcium channel blocker, in man following oral administration of its sustained release formulation. Xenobiotica, 27, 203-216.
33. VERONESE, M. K., 1991, Tolbutamide and phenytion metabolism by human cytochrome P450s in the CYP2C subfamily. Clinical and Experimental Pharmacology and Physiology 18 (suppl.), 64.
34. WANG, R. W., KARI, P. H., LU, A. Y. H., THOMAS, P. E., GUENGERICH, F. P. and VYAS, K. P., 1991, Biotransformation of lovastatin. IV. Identification of cytochrome P450 3A proteins as the major enzymes responsible for the oxidative metabolism of lovastatin in rat and human liver microsomes. Archives of Biochemistry and Biophysics, 290, 355-361.
35. WEIDORE, L., BORG, K. O. and HOFFMANN, K. J., 1984, Urinary metabolites of felodipine, a new vasodilator drug, in man, dog, rat and mouse. Xenobiotica, 14, 657-666.