The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazine neuroleptics

European Neuropsychopharmacology

Volumn 12, Issue 5, 2002, Pages 371-377

  Daniel, W A ^a   Syrek, M ^a   Haduch, A ^a  

^a INSTITUTE OF PHARMACOLOGY   (Poland)

Author keywords

Cytochrome P 450 isoenzymes; Metabolism; Perazine; Promazine; Specific inhibitors; Thioridazine

Indexed keywords

ALPHA NAPHTHOFLAVONE; CYTOCHROME P450 1A2; CYTOCHROME P450 2B2; CYTOCHROME P450 ISOENZYME; ERYTHROMYCIN; NEUROLEPTIC AGENT; PERAZINE; PHENOTHIAZINE DERIVATIVE; PROMAZINE; QUININE; SULFAPHENAZOLE; THIORIDAZINE;

ANIMAL CELL; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG METABOLISM; DRUG TRANSFORMATION; LIVER MICROSOME; MALE; METHYLATION; NONHUMAN; PRIORITY JOURNAL; RAT;

ALCOHOL OXIDOREDUCTASES; ANALGESICS, NON-NARCOTIC; ANIMALS; ANTIPSYCHOTIC AGENTS; ARYL HYDROCARBON HYDROXYLASES; BENZOFLAVONES; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG INTERACTIONS; ENZYME INHIBITORS; ISOENZYMES; KINETICS; MALE; METHYLATION; METYRAPONE; MICROSOMES, LIVER; OXIDATION-REDUCTION; OXIDOREDUCTASES, N-DEMETHYLATING; PERAZINE; PROMAZINE; QUININE; RATS; RATS, WISTAR; STEROID HYDROXYLASES; SUBSTRATE SPECIFICITY;

EID: 0036787071     PISSN: 0924977X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0924-977X(02)00053-6     Document Type: Article

References (33)

1. Baldwin S.J., Bloomer J.C., Smith G.J., Ayrton A.D., Clarke S.E., Chenery R.J. Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica. 25:1995;261-270.
2. Blake B.L., Rose R.L., Mailman R.B., Levi P.E., Hodgson E. Metabolism of thioridazine by microsomal monooxygenases: relative roles of P-450 and flavin-containing monooxygenase. Xenobiotica. 25:1995;377-393.
3. Boobis A.R., Sesardic D., Merray B.P., Edwards R.J., Singleton A.M., Rich K.J., Murray S., De La Torre R., Segura J., Pelkonen O., Pasanen O., Kobayashi S., Zhi-Guang T., Davies D.S. Species variation in the response of the cytochrome P-450-dependent monooxygenase system to inducers and inhibitors. Xenobiotica. 11:1990;1139-1161.
4. Breyer U. Urinary metabolites of 10-[3′-(4″-methylpiperazinyl)-propyl]-phenothiazine (Perazine) in psychiatric patients - I. Isolation, identification and determination of metabolites. Biochem. Pharmacol. 18:1969;777-788.
5. Cashman J.R., Yang Z., Yang L., Wrighton S. Stereo- and regioselective N- and S-oxidation of tertiary amines and sulfides in the presence of adult human liver microsomes. Drug Metab. Dispos. 21:1993;492-501.
6. Dahl M.L., Bertilsson L. Genetically variable metabolism of antidepressant and neuroleptic drugs. Pharmacogenetics. 3:1993;61-70.
7. Dahl-Puustinen M.L., Liden A., Alm C., Nordin C., Bertilsson L. Disposition of perphenazine is related to the polymorphic hydroxylation in human beings. Clin. Pharmacol. Ther. 46:1989;78-81.
8. Daniel W.A., Syrek M., Janczar L., Boksa J. The pharmacokinetics of promazine and its metabolites after acute and chronic administration to rats - A comparison with the pharmacokinetics of imipramine. Pol. J. Pharmacol. 47:1995;127-136.
9. Daniel W.A., Syrek M., Haduch A. The effects of selective cytochrome P-450 inhibitors on the metabolism of thioridazine. In vitro studies. Pol. J. Pharmacol. 51:1999;435-442.
10. Daniel W.A., Syrek M., Haduch A., Wójcikowski J. Different effects of amitriptyline and imipramine on the pharmacokinetics and metabolism of perazine in rats. J. Pharm. Pharmacol. 52:2000;1473-1481.
11. Daniel W.A., Syrek M., Wójcikowski J. The influence of selective serotonin reuptake inhibitors on the plasma and brain pharmacokinetics of the simplest phenothiazine neuroleptic promazine in the rat. Eur. Neuropsychopharmacol. 9:1999;337-344.
12. Daniel W.A., Syrek M., Mach A., Wójcikowski J., Boksa J. Pharmacokinetics of thioridazine and its metabolites in blood plasma and the brain of rats after acute and chronic treatment. Pol. J. Pharmacol. 49:1997;439-452.
13. i. Biochem. J. 129:1972;197-202.
14. Ealing V.A., Tjia I.F., Back D.J. Differential selectivity of cytochrome P-450 inhibitors against probe substrates in human and rat liver microsomes. Br. J. Clin. Pharmacol. 45:1998;107-114.
15. Ghosal A., Satoh H., Thomas P., Bush E., Moore D. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab. Dispos. 24:1996;940-947.
16. Goldenberg H., Fishman F., Heaton A. A detailed evaluation of promazine metabolism. J. Pharmacol. Exp. Ther. 150:1965;122-128.
17. Jerling M., Dahl M.-L., Aberg-Wisted A., Liljenberg B., Landell N.-E., Bertilsson L. The CYP2D6 genotype predicts the oral clearance of the neuroleptic agents perphenazine and zuclopenthixol. Clin. Pharmacol. Ther. 59:1996;423-428.
18. Kanig K., Breyer U. Urinary metabolites of 10-[3′-(4″-methylpiperazinyl)-propyl]-phenothiazine (Perazine) in psychiatric patients - II. Individual metabolite patterns and their changes in the course of treatment. Psychopharmacologia (Berl.). 14:1969;211-220.
19. Kobayashi S., Murray S., Watson D., Sesardic D., Davies D.S., Boobis A.R. 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;2795-2799.
20. Llerna A., Herraiz A.G., Cobaleda J., Johansson I., Dahl M-L. Debrisoquin and mephenytoin hydroxylation phenotypes and CYP2D6 genotype in patients treated with neuroleptic and antidepressant agents. Clin. Pharmacol. Ther. 54:1996;606-611.
21. Meyer J.W., Woggon B., Baumann P., Meyer U.A. Clinical implications of slow sulphoxidation of thioridazine in a poor metabolizer of the debrisoquine type. Eur. J. Clin. Pharmacol. 39:1990;613-614.
22. Murray M., Reidy G.F. Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents. Pharmacol. Rev. 42:1990;85-101.
23. Okey A.B. Enzyme induction in the cytochrome P450 system. Pharmacol. Ther. 45:1990;241-298.
24. Parmar D., Dhawan A., Seth P.K. Evidence for O-dealkylation of 7-pentoxyresorufin by cytochrome P450 2B1/2B2 isoenzymes in brain. Mol. Cell. Biochem. 189:1998;201-205.
25. Sesardic D., Boobis A.R., Murray B.P., Murray S., Segura J., De La Torre R., Davies D.S. Furafylline is a potent and selective inhibitor of cytochrome P4501A2 in man. Br. J. Pharmacol. 29:1990;651-663.
26. Shimada T., Yamazaki H., Mimura M., Inui Y., Guengerich F.P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogenes and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther. 270:1994;414-423.
27. Shimojo N., Ishizaki T., Imaoka S., Funae Y., Fujii S., Okuda K. Changes in amounts of cytochrome P450 isoenzymes and levels of catalytic activities in hepatic and renal microsomes of rats with streptozotocin-induced diabetes. Biochem. Pharmacol. 46:1993;621-627.
28. Steiner E., Dumond E., Spina E., Dahlqvist R. Inhibition of desipramine 2-hydroxylation by quinidine and quinine. Clin. Pharmacol. Ther. 43:1988;577-581.
29. Störmer E., Bröckmöller J., Roots I., Schmieder J. Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro. Psychopharmacology. 151:2000;312-320.
30. Syvälahti E.K.G., Lindberg R., Kallio J., De Vocht M. Inhibitory effects of neuroleptics on debrisoquine oxidation in man. Br. J. Pharmacol. 22:1986;89-92.
31. Valoti M., Frosini M., Palmi M., De Matteis F., Sgaragli G. N-Dealkylation of chlorimipramine and chlorpromazine by rat liver microsomal cytochrome P450 isoenzymes. J. Pharm. Pharmacol. 50:1998;1005-1011.
32. Wrighton S.A., Stevens J.C. The human hepatic cytochromes P450 involved in drug metabolism. Crit. Rev. Toxicol. 22:1992;1-21.
33. Zhi-Guang T., Murray B., Sesardic D., Kobayashi S., Murray S., Davies D.S., Boobis A.R. Quinidine discriminates between rat and human debrisoquine 4-hydroxylase. Br. J. Clin. Pharmacol. 25:1988;674.