Comparative study of the oxidation of propranolol enantiomers in hepatic and small intestinal microsomes from cynomolgus and marmoset monkeys

Chemico-Biological Interactions

Volumn 183, Issue 1, 2010, Pages 67-78

  Shimizudani, Takeshi ^a   Nagaoka, Kenjiro ^a   Hanioka, Nobumitsu ^a   Yamano, Shigeru ^b   Narimatsu, Shizuo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b FUKUOKA UNIVERSITY   (Japan)

Author keywords

Antibody; Cynomolgus monkey; Hepatic and small intestinal microsomes; Inhibitor; Marmoset; Propranolol enantiomer

Indexed keywords

4 HYDROXYPROPRANOLOL; 5 HYDROXYPROPRANOLOL; CYTOCHROME; CYTOCHROME P450 1A; CYTOCHROME P450 2C; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D; CYTOCHROME P450 2D6; CYTOCHROME P450 3A; CYTOCHROME P450 3A4; DEISOPROPYLPROPRANOLOL; DRUG METABOLITE; DRUG METABOLIZING ENZYME; ENZYME ANTIBODY; N DEISOPROPYLASE; OXYGENASE; PROPRANOLOL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME SUBSTRATE; LIVER MICROSOME METABOLISM; MARMOSET; MICROSOME; MONKEY; SMALL INTESTINE;

ANIMALS; ANTIBODIES; CALLITHRIX; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; INTESTINE, SMALL; KINETICS; LIVER; MACACA FASCICULARIS; MICROSOMES; OXIDATION-REDUCTION; PROPRANOLOL; STEREOISOMERISM;

MACACA FASCICULARIS; MARMOSETS;

EID: 71349085539     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2009.10.007     Document Type: Article

References (31)

1. Stevens J.C., Shipley L.A., Cashman J.R., Vandenbranden M., and Wrighton S.A. Comparison of human and rhesus monkey in vitro phase I and phase II hepatic drug metabolism activities. Drug Metab. Dispos. 21 (1993) 753-760
2. Sharer J.E., Shipley L.A., Vandenbranden M.R., Binkley S.N., and Wrighton S.A. Comparisons of phase I and phase II in vitro hepatic enzyme activities of human, dog, rhesus monkey, and cynomolgus monkey. Drug Metab. Dispos. 23 (1995) 1231-1241
3. Guengerich F.P. Comparisons of catalytic selectivity of cytochrome P450 subfamily enzymes from different species. Chem. Biol. Interact. 106 (1997) 161-182
4. Shimada T., Mimura M., Inoue K., Nakamura S., Oda H., Ohmori S., and Yamazaki H. Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys, and humans. Arch. Toxicol. 71 (1997) 401-408
5. Weaver R.J., Dickins M., and Burke M.D. A comparison of basal and induced hepatic microsomal cytochrome P450 monooxygenase activities in the cynomolgus monkey (Macaca fascicularis) and man. Xenobiotica 29 (1999) 467-482
6. Narimatsu S., Gotoh M., Masubuchi Y., Horie T., Ohmori S., Kitada M., Kageyama T., Asaoka K., Yamamoto I., and Suzuki T. Stereoselectivity in bunitrolol 4-hydroxylation in liver microsomes from marmosets and Japanese monkeys. Biol. Pharm. Bull. 19 (1996) 1429-1433
7. Narimatsu S., Kobayashi N., Masubuchi Y., Horie T., Kakegawa T., Kobayashi H., Hardwick J.P., Gonzalez F.J., Shimada N., Ohmori S., Kitada M., Asaoka K., Kataoka H., Yamamoto S., and Satoh T. Species difference in enantioselectivity for the oxidation of propranolol by cytochrome P450 2D enzymes. Chem. Biol. Interact. 127 (2000) 73-90
8. Narimatsu S., Kobayashi N., Asaoka K., Masubuchi Y., Horie T., Hosokawa M., Ishikawa T., Ohmori S., Kitada M., Miyano J., Kataoka H., and Yamamoto S. High-performance liquid chromatographic analysis of the sulfation of 4-hydroxypropranolol enantiomers by monkey liver cytosol. Chirality 13 (2001) 140-147
9. Hichiya H., Takemi C., Tsuzuki D., Yamamoto S., Asaoka K., Suzuki S., Satoh T., Shinoda S., Kataoka H., and Narimatsu S. Complementary DNA cloning and characterization of cytochrome P450 2D29 from Japanese monkey liver. Biochem. Pharmacol. 64 (2002) 1101-1110
10. Narimatsu S., Oda M., Hichiya H., Isobe T., Asaoka K., Hanioka N., Yamano S., Shinoda S., and Yamamoto S. Molecular cloning and functional analysis of cytochrome P450 1A2 from Japanese monkey liver: comparison with marmoset cytochrome P450 1A2. Chem. Biol. Interact. 152 (2005) 1-12
11. Hanioka N., Takeda Y., Jinno H., Tanaka-Kagawa T., Naito S., Koeda A., Shimizu T., Nomura M., and Narimatsu S. Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A6 enzymes. Chem. Biol. Interact. 164 (2006) 136-145
12. Hanioka N., Yamamoto M., Iwabu H., Jinno H., Tanaka-Kagawa T., Naito S., Shimizu T., Masuda K., Katsu T., and Narimatsu S. Functional characterization of human and cynomolgus monkey cytochrome P450 2E1 enzymes. Life Sci. 81 (2007) 1436-1445
13. Hanioka N., Hayashi K., Shimizudani T., Nagaoka K., Koeda A., Naito S., and Narimatsu S. Stereoselective glucuronidation of propranolol in human and cynomolgus monkey liver microsomes: role of human hepatic UDP-glucuronosyltransferase isoforms, UGT1A9, UGT2B4 and UGT2B7. Pharmacology 82 (2008) 293-303
14. Hichiya H., Kuramoto S., Yamamoto S., Shinoda S., Hanioka N., Narimatsu S., Asaoka K., Miyata A., Iwata S., Nomoto M., Satoh T., Kiryu K., Ueda N., Naito S., Tucker G.T., and Ellis S.W. Cloning and functional expression of a novel marmoset cytochrome P450 2D enzyme, CYP2D30: comparison with the known marmoset CYP2D19. Biochem. Pharmacol. 68 (2004) 165-175
15. Narimatsu S., Torigoe F., Sumada T., Tsuneto Y., Saito K., Hanioka N., Masuda K., Katsu T., Yamamoto S., Yamano S., Baba T., and Miyata A. Cloning of a cDNA encoding a novel marmoset CYP2C enzyme, expression in yeast cells and characterization of its enzymatic functions. Biochem. Pharmacol. 72 (2006) 1738-1748
16. Barret A.M., and Cullim V.A. The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias. Br. J. Pharmacol. 34 (1968) 43-55
17. Silber B., and Riegelman S. Stereospecific assay for (-)- and (+)-propranolol in human and dog plasma. J. Pharmacol. Exp. Ther. 25 (1980) 643-648
18. Nies A.S., and Shand D.G. Clinical pharmacology of propranolol. Circulation 52 (1975) 6-15
19. Walle T., Walle U.K., and Olanoff L.S. Quantative metabolic fate of prorpanolol metabolism in urine of normal man. Drug Metab. Dispos. 13 (1985) 204-209
20. Walle T. Stereochemistry of in vivo disposition and metabolism of propranolol in dog and man using deuterium-labeled pseudoracemates. Drug Metab. Dipsos. 13 (1985) 279-282
21. Silber B., Holford N.H., and Riegelman S. Stereoselective disposition and glucuronidation of propranolol in human. J. Pharm. Sci. 71 (1982) 699-704
22. Masubuchi Y., Hosokawa S., Horie T., Suzuki T., Ohmori S., Kitada M., and Narimatsu S. Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes: the role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-deisopropylase. Drug Metab. Dispos. 22 (1994) 909-915
23. Ding X., and Kaminsky L.S. Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu. Rev. Pharmacol. Toxicol. 43 (2002) 149-173
24. Pal D., and Mitra A.K. MDR- and CYP3A4-mediated drug-drug interaction. J. Neuroimmunol. Pharmacol. 1 (2006) 323-339
25. Clarke S.E., Ayrton A.D., and Chenery R.J. Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica 24 (1994) 517-526
26. Walsky R.L., Obach R.S., Gaman E.A., Gleeson J.P., and Proctor W.R. Selective inhibition of human cytochrome P4502C8 by montelukast. Drug Metab. Dispos. 33 (2004) 413-418
27. Suzuki H., Kneller B., Haining R.L., Trager W.F., and Rettie A.E. (+)-N-3-Benzylnirvanol and (+)-N-3-benzylphenobarbital: new potent and selective in vitro inhibitors of CYP2C19. Drug Metab. Dispos. 30 (2002) 235-239
28. Kobayashi S., Murray S., Watson D., Serardic D., Davies D.S., and Boobis A.R.E. The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochem. Pharmacol. 38 (1989) 2795-2797
29. Mankowski D.C., Laddison K.J., Christopherson P.A., Ekins S., Tweedie D.J., and Lawton M.P. Molecular cloning, expression, and characterization of CYP2D17 from cynomolgus monkey liver. Arch. Biochem. Biophys. 372 (1999) 189-196
30. Hichiya H., Takemi C., Tsuzuki D., Yamamoto S., Asaoka K., Suzuki S., Satoh T., Shinoda S., Kataoka H., and Narimatsu S. Cloning and functional expression of a novel marmoset cytochrome P450 2D enzyme, CYP2D30: comparison with the known marmoset CYP2D19. Biochem. Pharmacol. 68 (2004) 165-175
31. Nishimura M., Koeda A., Suganuma Y., Suzuki E., Shimizu T., Nakayama M., Satoh T., Narimatsu S., and Naito S. Comparison of inducibility of CYP1A and CYP3A mRNAs by prototypical inducers in primary cultures of human, cynomolgus monkey, and rat hepatocytes. Drug Metab. Pharmacokinet. 22 (2007) 178-186