Metabolism of carteolol by cDNA-expressed human cytochrome P450

European Journal of Clinical Pharmacology

Volumn 52, Issue 6, 1997, Pages 479-485

  Kudo, S ^a   Uchida, M ^a   Odomi, M ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

8 hydroxycarteolol,; Biotransformation; Carteolol; CDNA expressed microsomes; CYP2D6

Indexed keywords

BIPERIDEN; BUFURALOL; CARTEOLOL; CHLORZOXAZONE; CYTOCHROME P450 ISOENZYME; DEXTROMETHORPHAN; DRUG METABOLITE; MEPHENYTOIN; NORTRIPTYLINE; PROPRANOLOL; QUINIDINE; SPARTEINE; TESTOSTERONE; TOLBUTAMIDE; WARFARIN;

ARTICLE; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; PRIORITY JOURNAL;

CARTEOLOL; CELL LINE; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; HUMANS; HYDROXYLATION; MICROSOMES;

EID: 0030766298     PISSN: 00316970     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002280050322     Document Type: Article

References (45)

1. Nakagawa K, Murakami N, Yoshizaki S, Tominaga M, Mori H, Yabuuchi Y, Shintani S (1974) Derivatives of 3,4-dihydrocarbostyril as β-adrenergic blocking agents. J Med Chem 17: 529-533
2. Yabuuchi Y, Kinoshita D (1974) Cardiovascular studies of 5-(3-tert-butylamino-2-hydroxy) propoxy-3,4-dihydrocarbostyril hydrochloride (OPC-1085), a new potent β-adrenergic blocking agent. Jpn J Pharmacol 24: 853-861
3. Kamimura M, Aoba A, Yamaguchi N, Tsuneizumi T, Takagi H, Chishima T, Sakai T, Negishi K, Morokawa Y, Takeshita T, Ohta T, Kishiro M, Hirakawa Y, Hasegawa K (1992) The clinical effect of carteolol hydrochloride on neuroleptic-induced akathisia. St Marianna Med J 20: 173-181
4. Fleischhacker WW, Roth SD, Kane JM (1990) The pharmacologic treatment of neuroleptic-induced akathisia. J Clin Psychopharmacol 10: 12-21
5. Mori H, Kido M, Murakami N, Morita S, Kohri H, Nakagawa K, Uno T, Ishihara T (1977) Metabolic fate of carteolol hydrochloride [5-(3-tert-butylamino-2-hydroxy-propoxy)-3,4-dihydrocarbostyril hydrochloride, OPC-1085], a new β-blocker. V. Identification of metabolites in rat, dog and human. Yakagaku Zasshi 97: 350-358
6. Wrighton SA, Stevens JC (1992) The human hepatic cytochrome P450 involved in drug metabolism. Crit Rev Toxicol 22: 1-21
7. Gonzalez FJ, Gelhoin HV (1993) Role of human cytochrome P450s in risk assessment and susceptibility to environmentally based disease. J Toxicol Environ Health 40: 289-308
8. Birkett DJ, Mackenzie PI, Veronese ME, Miners JO (1993) In vitro approaches can predict human drug metabolism. Trends Pharmacol Sci 14: 292-294
9. Tarbit MH, Bayliss MK, Herriott D, Hood SR, Hutson JL, Park GR, Serabjit-Singh CJ (1993) Applications of molecular biology and in vitro technology to drug metabolism studies: an industrial perspective. Biochem Soc Trans 21: 1018-1023
10. Morita S, Iinuma M, Kido M, Sakuragi S, Kohri H, Nishino H (1977) Metabolic fate of carteolol hydrochloride, (OPC-1085) VIII, a new β-adrenergic blocking agent. Arzneimittelforschung 27: 2380-2383
11. West BD, Preis S, Schroeder CH, Link KP (1961) Studies on the 4-hydroxycoumarins. XVII. The resolution and absolute configuration of warfarin. J Am Chem Soc 83: 2676-2679
12. Otton SV, Inaba T, Kalow W (1984) Competitive inhibition of sparteine oxidation in human liver by β-adrenoceptor antagonists and other cardiovascular drugs. Life Sci 34: 73-80
13. Inaba T, Jurima M, Mahon WA, Kalow W (1985) In vitro inhibition studies of two isozymes of human liver cytochrome P-450. Mephenytoin p-hydroxylase and sparteine monooxygenase. Drug Metab Dispos 13: 443-448
14. Guengerich FP, Müller-Enoch D, Blair IA (1986) Oxidation of quinidine by human liver cytochrome P-450. Mol Pharmacol 30: 287-295
15. Gut J, Catin T, Dayer P, Kronbach T, Zanger LJ, Meyer UA (1986) Debrisoquine/sparteine-type polymorphism of drug oxidation. Purification and characterization of two functionally different human liver cytochrome P-450 isozymes involved in impaired hydroxylation of the prototype substrate bufuralol. J Biol Chem 261: 11734-11743
16. Otton SV, Crewe HK, Lennard MS, Tucker GT, Woods HF (1988) Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. J Pharmacol Exp Ther 247: 242-247
17. Bresen K, Zeugin T, Meyer UA (1991) Role of P450IID6, the target of the sparteine-debrisoquine oxidation polymorphism, in the metabolism of imipramine. Clin Pharmacol Ther 49: 609-617
18. 2 and cumene hydroperoxide-supported reactions. Drug Metab Dispos 24: 112-118
19. Pfandl B, Morike K, Winne D, Schareck W, Breyer-Pfaff U (1992) Stereoselective inhibition of nortriptyline hydroxylation in man by quinidine. Xenobiotica 22: 721-730
20. Wu D, Otton SV, Morrow P, Inaba T, Kalow W, Sellers EM (1993) Human hepatic cytochrome P450 2D6-like activity in nonhuman primates: catalytic characterization in vitro. J Pharmacol Exp Ther 266: 715-719
21. Tyndale RF, Inaba T, Kalow W (1989) Evidence in humans for variant allozymes of the nondeficient sparteine/debrisoquine monooxygenase (P450IID1) in vitro. Drug Metab Dispos 17: 334-340
22. Minder EI, Meier PJ, Müller HK, Minder C, Meyer UA (1984) Bufuralol metabolism in human liver: a sensitive probe for the debrisoquine-type polymorphism of drug oxidation. Eur J Clin Invest 14: 184-189
23. Kahn GC, Boobis AR, Murray S, Brodie MJ, Davies DS (1982) Assay and characterisation of debrisoquine 4-hydroxylase activity of microsomal fractions of human liver. Br J Clin Pharmacol 13: 637-645
24. Marre F, Fabre G, Lacarelle B, Bourrie M, Catalin J, Berger Y, Rahmani R, Cano JP (1992) Involvement of the cytochrome P-450IID subfamily in minaprine 4-hydroxylation by human hepatic microsomes. Drug Metab Dispos 20: 316-321
25. Appanna G, Tang BK, Müller R, Kalow W (1996) A sensitive method for determination of cytochrome P4502D6 activity in vitro using bupranolol as substrate. Drug Metab Dispos 24: 303-306
26. Tyndale RF, Kalow W, Inaba T (1991) Oxidation of reduced haloperidol to haloperidol: involvement of human P450IID6 (sparteine/debrisoquine monooxygenase). Br J Clin Pharmacol 31:655-660
27. Rettie AK, Korzekwa KR, Kunze KL, Lawrence RF, Eddy AC, Aoyama T, Gelboin HV, Gonzalez FJ, Trager WF (1992) Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: a role for P-450 2C9 in the etiology of (S)-warfarin-drug interactions. Chem Res Toxicol 5: 54-59
28. Hollmann M, Brode E, Greger G, Müller-Peltzer H, Wetzelsberger N (1984) Biperiden effects and plasma levels in volunteers. Eur J Clin Pharmacol 27: 619-621
29. Grimaldi R, Perucca E, Ruberto G, Gelmi C, Trimarchi F, Hollmann M, Crema A (1986) Pharmacokinetic and pharmacodynamic studies following the intravenous and oral administration of the antiparkinsonian drug biperiden to normal subjects. Eur J Clin Pharmacol 29: 735-737
30. Parkinson A (1996) Biotransformation of xenobiotics. In: DD Kloassen (ed) Casarett and Doull's Toxicology, the basic science of poisons. McGraw-Hill, New York, pp. 113-186
31. Shimada T, Yamazaki H, Mimura M, Inui Y, 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
32. Guengerich FP (1989) Polymorphism of cytochrome P-450 in humans. Trends Pharmacol Sci 10: 107-109
33. Relling MV (1989) Polymorphic drug metabolism. Clin Pharm 8: 852-863
34. Meyer UA, Zanger UM, Grant D, Blum M (1990) Genetic polymorphisms of drug metabolism. Adv Drug Res 19: 198-241
35. Back DJ, Sutcliffe F, Tjia JF (1984) Tolbutamide as a model drug for the study of enzyme induction and enzyme inhibition in the rat. Br J Pharmacol 81: 557-562
36. Brian WR, Srivastava PK, Umbenhauer DR, Lloyd RS, Guengerich FP (1989) Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in Saccharomyces cerevisiae. Biochemistry 28: 4993-4999
37. Relling MV, Aoyama T, Gonzalez FJ, Meyer UA (1990) Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. J Pharmacol Exp Ther 252: 442-447
38. Jurima M, Inaba T, Kalow W (1985) Mephenytoin metabolism in vitro by human liver. Drug Metab Dispos 13: 151-155
39. Peter R, Böcker R, Beaune PH, Iwasaki M, Guengerich FP, Yang CS (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem Res Toxicol 3: 566-573
40. Tassaneeyakul W, Veronese ME, Birkett DJ, Gonzalez FJ, Miners JO (1993) Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem Pharmacol 46: 1975-1981
41. Carriere V, Goasduff T, Ratanasavanh D, Morel F, Gautier JC, Guillouzo A, Beaune P, Berthou F (1993) Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chem Res Toxicol 6: 852-857
42. Waxman DJ, Attisano C, Guengerich FP, Lapenson DP (1988) Human liver microsomal steroid metabolism: identification of the major microsomal steroid hormone 6β-hydroxylase cytochrome P-450 enzyme. Arch Biochem Biophys 263: 424-436
43. Brian WR, Sari MA, Iwasaki M, Shimada T, Kaminsky LS, Guengerich FP (1990) Catalytic activities of human liver cytochrome P-450IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry 29: 11280-11292
44. Newton DJ, Wang RW, 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
45. Lennard MS (1989) The polymorphic oxidation of beta-adrenoceptor antagonists. Pharmacol Ther 41: 461-477