The role of CYP2C19 in the metabolism of (+/-) bufuralol, the prototypic substrate of CYP2d6

Drug Metabolism and Disposition

Volumn 27, Issue 9, 1999, Pages 1024-1028

  Mankowski, Dayna C ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUFURALOL; CYTOCHROME P450; MEPHENYTOIN; QUINIDINE; QUININE; RECOMBINANT ENZYME; TICLOPIDINE;

ARTICLE; BACULOVIRUS; DRUG INHIBITION; ENZYME ACTIVITY; ENZYME METABOLISM; HUMAN; HUMAN CELL; HYDROXYLATION; LIVER MICROSOME; MICHAELIS CONSTANT; NONHUMAN; PRIORITY JOURNAL;

ADRENERGIC BETA-ANTAGONISTS; ANTICONVULSANTS; ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 ENZYME SYSTEM; ETHANOLAMINES; HUMANS; KINETICS; MEPHENYTOIN; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; QUINIDINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

CINCHONA PUBESCENS; UNIDENTIFIED BACULOVIRUS;

EID: 0032841888     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Asseffa A, Smith SJ, Nagata K, Gillette J, Gelboin H and Gonzalez FJ (1989) Novel exogenous heme-dependent expression of mammalian cytochrome P-450 using baculovirus. Arch Biochem Biophys 274:481-490.
2. Boobis AR, Murray S, Hampden CE and Davies DS (1985) Genetic polymorphism in drug oxidation: In vitro studies of human debrisoquine 4-hydroxylase and bufuralol 1′-hydroxylase activities. Biochem Pharmacol 34:65-71.
3. Bourrie M, Meunier V, Berger Y and Fabre G (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277:321-332.
4. Ching MS, Blake CL, Ghabrial H, Ellis SW and Lennard MS (1995) Potent inhibition of yeast-expressed CYP2D6 by dihydroquinidine, quinidine, and its metabolites. Biochem Pharmacol 50:833-837.
5. Dayer P, Leeman T, Gut J, Kronbach T, Kupfer A, Francis R and Meyer UA (1985) Steric configuration and polymorphic oxidation of lipophilic beta-adrenoceptor blocking agents: In vivo and in vitro correlations. Biochem Pharmacol 34:399-400.
6. Donahue SR, Flockhart DA, Abemethy DR and Ko J-W (1997) Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19. Clin Pharmacol Ther 62:572-577.
7. Ekins S, VandenBranden M, Ring BJ and Wrighton SA (1997) Examination of purported probes of human CYP2B6. Pharmacogenetics 7:165-179.
8. Gelboin HV, Krausz KW, Shou M, Gonzalez FJ and Yang TJ (1997) A monoclonal antibody inhibitory to human P450 2D6: A paradigm for use in combinatorial determination of individual P450 role in specific drug tissue metabolism. Pharmacogenetics 7:469-477.
9. Guengerich FP (1977) Separation and purification of multiple forms of microsomal cytochrome P450. J Biol Chem 252:3970-3979.
10. Gut J, Catin T, Dayer P, Kronbach T, Zanger U and Meyer UA (1986) Debrisoquine/sparteine-type polymorphism of drug oxidation. Purification and characterization of two functionally different human liver cytochrome P450 isozymes involved in impaired hydroxylation of the prototype substrate bufuralol. J Biol Chem 261:11734-11743.
11. Kimura M, Ieiri I, Mamiya K, Urae A and Higuchi S (1998) Genetic polymorphism of cytochrome P450s, CYP2C19, and CYP2C9 in a Japanese population. Ther Drug Monit 20:243-247.
12. Kivisto KT and Kroemer HK (1997) Use of probe drugs as predictors of drug metabolism in humans. J Clin Pharmacol 37:40S-48S.
13. Ko J-W, Sukhova N, Oakes S and Flockhart DA (1998) Ticlopidine is a potent inhibitor of CYP2C19 and CYP2D6 in vitro (abstract). Clin Pharm Ther 63:175.
14. Kronbach T, Mathys D, Gut J, Catin T and Meyer UA (1987) High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P450 isozymes of human liver. Anal Biochem 162:24-32.
15. th International Symposium on Microsomes and Drug Oxidations, p 176, poster 55; 1996 July 21-24; University of California, Los Angeles.
16. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M and Narimatsu S (1994) Cytochrome P450 isoenzymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as human N-desisopropylase. Drug Metab Dispos 22:909-915.
17. Meyer UA, Gut J, Kronbach T, Skoda C, Meier UT and Catin T (1986) The molecular mechanisms of two common polymorphisms of drug oxidation - Evidence for functional changes in cytochrome P-450 isozymes catalysing bufuralol and mephenytoin oxidation. Xenobiotica 16:449-464.
18. Nakamura K, Goto F, Ray WA, McAllister CB, Jacqz E, Wilkinson G and Branch RA (1985) Interethnic differences in genetic polymorphism of debrisoquin and mephenytoin hydroxylation between Japanese and Caucasian populations. Clin Pharmacol Ther 38:402-408.
19. Newton DJ, Wang RW and Lu AYH (1995) Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 23:154-158.
20. Omura T and Sato R (1964) The carbon monoxide-binding pigment of human liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
21. Ono S, Hatanaka T, Hotta H, Satoh T, Gonzalez FJ and Tsutsu, M (1996) Specificity of substrate and inhibitor probes for cytochrome P450s: Evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica 26:681-693.
22. Otton SV, Gillam EMJ, Leonard MS, Tucker GT and Woods HF (1990) Propranolol oxidation by human liver microsomes - The use of cumene hydroperoxide to probe isoenzyme specificity and regio-and stereoselectivity. Br J Clin Pharmacol 30:751-760.
23. Rendic S and Di Carlo FJ (1997) Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29:413-580.
24. 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.
25. Roussel F, Duignan DB, Lawton MP, Obach RS, Strick CA and Tweedie DJ (1998) Expression and characterization of canine cytochrome P450 2D15. Arch Biochem Biophys 357:27-36.
26. Sowinski KM and Burlew BS (1997) Impact of CYP2D6 poor metabolizer phenotype on propranolol pharmacokinetics and response. Pharmacotherapy 17:1305-1310.
27. Ward SA, Walle T, Walle K, Wilkinson GR and Branch RS (1989) Propranolol's metabolism is determined by both mephenytoin and debrisoquin hydroxylase activities. Clin Pharmacol Ther 45:72-79.
28. Wrighton SA and Stevens JC (1992) The human cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 22:1-21.
29. 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.
30. Yoshimoto K, Echizen H, Chiba K, Tani M and Ishikazi T (1995) Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers: N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol 39:421-431.