Bioactivation of carbamazepine in the rat in vivo: Evidence for the formation of reactive arene oxide(s)

Drug Metabolism and Disposition

Volumn 24, Issue 4, 1996, Pages 469-479

  Madden, Stephen ^a   Maggs, James L ^a   Park, B Kevin ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMAZEPINE; EPOXIDE HYDROLASE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BILIARY EXCRETION; BIOTRANSFORMATION; CONTROLLED STUDY; DNA ADDUCT; DRUG MECHANISM; DRUG METABOLISM; GLUCURONIDATION; HYDROLYSIS; IN VIVO STUDY; NONHUMAN; OXYGENATION; PRIORITY JOURNAL; RAT; TRIGEMINUS NEURALGIA;

ANIMALS; BILE; CARBAMAZEPINE; CHROMATOGRAPHY, LIQUID; GLUCURONATES; MALE; MASS SPECTROMETRY; RATS; RATS, WISTAR; SULFIDES; TISSUE DISTRIBUTION;

EID: 0029926719     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. L. Bertilsson and T. Tomson: Clinical pharmacokinetics and pharmacological effects of carbamazepine and carbamazepine-10,11-epoxide. An update. Clin. Pharmacokinet. 11, 177-198 (1986).
2. T. Tomson, G. Tybring, and L. Bertilsson: Single-dose kinetics and metabolism of carbamazepine-10,11-epoxide. Clin. Pharmacol. Ther. 33, 58-65 (1983).
3. F. N. Johnson and M. J. Brodie: Pharmacokinetics of CBZ: implications for clinical use. Rev. Contemp Pharmacother. 1, 85-98 (1990).
4. K. L. Jones, R. V. Lacro, K. A. Johnson, and J. Adams: Pattern of malformation in the children of women treated with carbamazepine during pregnancy. N. Engl. J. Med. 320, 1661-1666 (1989).
5. B. K. Park, M. Pirmohamed, and N. R. Kitteringham: Idiosyncratic drug reactions: a mechanistic evaluation of risk factors. Br. J. Clin. Pharmacol. 34, 377-395 (1992).
6. P. S. Friedmann, I. Strickland, M. Pirmohamed, and B. K. Park: Investigation of mechanisms of toxic epidermal necrolysis induced by carbamazepine. Arch. Dermatol. 130, 598-604 (1994).
7. S. Horowitz, B. Patwardhan, and E. Marcell: Hepatotoxic reactions associated with carbamazepine therapy. Epilepsia 29, 149-154 (1988).
8. D. Lindhout, R. J. Hoppener, and H. Meinardi: Teratogenicity of antiepileptic drug combinations with special emphasis on epoxidation (of carbamazepine). Epilepsia 25, 77-83 (1984).
9. M. Pirmohamed, N. R. Kitteringham, T. M. Guenthner, A. M. Breckenridge, and B. K. Park: An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro. Biochem. Pharmacol. 43, 1675-1682 (1992).
10. N. R. Kitteringham, M Pirmohamed, A. Gaedigk, D. M. Grant, and B. K. Park: Carbamazepine idiosyncratic toxicity: investigation of the role of microsomal epoxide hydrolase. Can. J. Physiol. Pharmacol. 72, 318 (abstr.) (1994).
11. R. K. Lynn, R. G. Smith, R. M. Thompson, M. L. Deinzer, D. Griffin, and N. Gerber: Characterization of glucuronide metabolites of carbamazepine in human urine by gas chromatography and mass spectrometry. Drug Metab. Dispos. 6, 494-501 (1978).
12. K. Lertratanangkoon and M. G. Horning: Metabolism of carbamazepine. Drug Metab. Dispos. 10, 1-10 (1982).
13. M. Eichelbaum, T. Tomson, G. Tybring, and L. Bertilsson: Carbamazepine metabolism in man: induction and pharmacogenetic aspects. Clin. Pharmacokinet. 10, 80-90 (1985).
14. C. Beyer and G. Spiteller: A new Carbamazepine metabolite in uraemic filtrate. Xenobiotica 22, 1029-1035 (1992).
15. P. L. Graver: Pathways involved in the metabolism and activation of polycyclic hydrocarbons. Xenobiotica 16, 915-931 (1986).
16. A. M. Jeffrey, H. J. C. Yeh, D. M. Jerina, R. M. De Marinis, C. H. Foster, D. E. Piccolo, and G. A. Berchtold: Stereochemical course in reactions between nucleophiles and arene oxides. J. Am. Chem. Soc. 96, 6929-6937 (1974).
17. J. M. te Koppele and G. J. Mulder: Stereoselective glutathione conjugation by subcellular fractions and purified glutathione S-transferases. Drug Metab. Rev. 23, 331-354 (1991).
18. A. Durand, J. P. Thenot, G. Bianchetti, and P. L. Morselli: Comparative pharmacokinetic profile of two imidazopyridine drugs: zolpidem and alpidem. Drug Metab. Rev. 24, 239-266 (1992).
19. Z. Gregus, C. Madhu, and C. D. Klaassen: Species variation in toxication and detoxication of acetaminophen in vivo: a comparative study of biliary and urinary excretion of acetaminophen metabolites. J. Pharmacol. Exp. Ther. 224, 91-99 (1988).
20. H. Jewell, J. L. Maggs, A. C. Harrison, P. M. O'Neill, J. E. Ruscoe, and B. K. Park: The role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica 25, 199-217 (1995).
21. D. Williams, J. L. Maggs, M. Pirmohamed, and B. K. Park: Bioactivation of clozapine in vitro and in vivo: implications for drug-induced agranulocytosis. Br. J. Clin. Pharmacol. 40, 182P (abstr.) (1995).
22. K. Lertratanangkoon, M. G. Horning, B. S. Middleditch, W.-S. Tsang, and G. W. Griffin: Urinary bivalent sulfur metabolites of phenanthrene excreted by the rat and guinea-pig. Drug Metab. Dispos. 10, 614-623 (1982).
23. J. E. Bakke: Metabolites derived from glutathione conjugation. In "Intermediary Xenobiotic Metabolism" (D. H. Hutson, J. Caldwell, and G. D. Paulson, eds.), pp. 205-224. Taylor and Francis, London, 1989.
24. M. Buonarati, A. D. Jones, and A. Buckpitt: In vivo metabolism of isomeric naphthalene oxide glutathione conjugates. Drug Metab. Dispos. 18, 183-189 (1990).
25. A. E. Mutlib and F. S. Abbott: Isolation and characterization of carbinolamide and phenolic glucuronide conjugates of (±)-N-methyl-N-(1-methyl-3,3-diphenylpropyl)formamide and N-formylmethamphetamine by FAB/MS. LC/MS/MS and NMR. Drug Metab. Dispos. 20, 451-460 (1992).
26. A. R. Buckpitt, N. Castagnoli, S. D. Nelson, A. D. Jones, and L. S. Bahnson: Stereoselectivity of naphthalene epoxidation by mouse, rat and hamster pulmonary, hepatic and renal microsomal enzymes. Drug Metab. Dispos. 15, 491-498 (1987).
27. 1 murine isolated perfused liver. Drug Metab. Dispos. 23, 129-136 (1995).
28. J. Zheng and R. P. Hanzlik: Premercapturic acid metabolites of bromobenzene derived via its 2-, 3- and 3,4-oxide metabolites. Xenobiotica 21, 535-546 (1991).
29. C. M. Murphy, C. Fenselau, and P. L. Gutierrez: Fragmentation characteristic of glutathione conjugates activated by high-energy collisions. J. Am. Soc. Mass. Spectrom. 3, 815-822 (1992).
30. L. D. Betowski, W. A. Korfmacher, J O. Lay, D. W. Potter, and J. A. Hinson: Direct analysis of rat bile for acetaminophen and two of its conjugated metabolites via thermospray liquid chromatography/mass spectrometry. Biomed. Environ. Mass Spectrom. 14, 705-709 (1987).
31. C. F. Fenselau and L. P. Johnson: Analysis of intact glucuronides by mass spectrometry and gas chromatography-mass spectrometry. Drug Metab. Dispos. 8, 274-283 (1980).
32. A. Frigerio, R. Fanelli, P. Biandrate, G. Passerini, P. L. Morselli, and S. Garattini: Mass spectrometric characterization of carbamazepine-10,11-epoxide, a carbamazepine metabolite isolated from human urine. J. Pharm. Sci. 61, 1144-1147 (1972).
33. T. A. Baille and M. R. Davis: Mass spectrometry in the analysis of glutathione conjugates. Biol. Mass. Spectrom. 22, 319-325 (1993).
34. N. H. Shear, S. P. Spielberg, M. Cannon, and M. Miler: Anticonvulsant hypersensitivity syndrome: in vitro risk assessment. J. Clin. Invest. 82, 1826-1832 (1988).
35. M. Pirmohamed, R. Allott, V. J. Green, N. R. Kitteringham, D. Chadwick, and B. K. Park: Lymphocyte microsomal epoxide hydrolase in patients on carbamazepine therapy. Br. J. Clin. Pharmacol. 37, 577-581 (1994).
36. S. M. Furst, P. Sukhai, R. A. McClelland, and J. P. Uetrecht: Covalent binding of carbamazepine oxidative metabolites to neutrophils. Drug Metab. Dispos. 23, 590-594 (1995).
37. L. Regnaud, G. Sirios, and S. Chakrabarti: Effect of four-day treatment with carbamazepine at different dose levels on microsomal enzyme induction, drug metabolism and drug toxicity. Pharmacol. Toxicol. 62, 3-6 (1988).
38. M. L. Bernal, J. Gazulla, M. A. Saenz, J. Lanuza, M. Bartolome, and B. Sinues: Sister-chromatid exchanges, chromosome aberrations, proliferating rate index and urinary thiothers in patients undergoing long-term therapy with carbamazepine. Mutat. Res. 271, 188 (abstr.) (1992).
39. H. R. Sullivan and R. B. Franklin: In vitro thiomethylation: studies with flumezapine. Drug Metab. Dispos. 13, 276-278 (1985).
40. R. P. Hanzlik, K. Hogberg, and C. M. Judson: Microsomal hydroxylation of specifically deuterated monosubstituted benzenes: evidence for direct aromatic hydroxylation. Biochemistry 23, 3048-3055 (1984).
41. B. Baier-Weber, A. Prox, H. Wachsmuth, and U. Breyer-Pfaff: Glucuronides of hydroxylated metabolites of amitriptyline and nortriptyline isolated from rat bile. Drug Metab. Dispos. 16, 490-496 (1988).
42. F. Oesch, N. Kaubisch, D. M. Jerina, and J. W. Daly: Hepatic epoxide hydrolase: structure-activity relationships for substrates and inhibitors. Biochemistry 10, 4858-4866 (1971).
43. A. Astrom, S. Maner, and J. W. De Pierre: Induction of liver epoxide hydolase, UDP-glucuronyl transferase and cytosolic glutathione transferase in different rodent species by 2-acetylaminofluorene or 3-methylcholanthrene. Xenobiotica 17, 155-163 (1987).
44. J. E. Bakke, J. K. Huwe, D. J. Mulford, and A. Bergman: Metabolism of 1,2.4-trichlorobenzene in rats: examination of thiol formation. Xenobiotica 22, 199-210 (1992).
45. M. Akagi, I. Aoki, and T. Uematsu: Studies on food additives. X. The metabolism of p-ethoxyphenylurea in the rabbit. Chem. Pharm. Bull. 14, 1-9 (1966).
46. J. V. Anderson, L. Dalgaard, and S. H. Hansen: Enzymic synthesis of two glucuronides of the hydroxyisoxazole GABA-agonist. THIP, and the in vivo glucuronidation of THIP in rats. Xenobiotica 19, 1399-1406 (1989).
47. N. J. Howard, C. D. Davis, R. L. Allort, S. Madden, M. Pirmohamed, N. R Kitteringham, and B. K. Park: Species variation in microsomal epoxide hydrolase activity. Br. J. Clin. Pharmacol. 40, 509P (abstr.) (1995).
48. B. M. Kerr, K. E. Thummel, C. J. Wurden, S. M. Klein, D. L. Kroetz, F. G. Gonzalez, and R. H. Levy: Human liver carbamazepine metabolism: role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochem. Pharmacol. 47, 1969-1979 (1994).
49. T. Ehmer and B. Burchill: Substrate specificites of two stably expressed human liver UDP-glucuronyltransferases of the UGT1 gene family. Drug Metab. Dispos. 21, 50-55 (1993).
50. M. D. Green, W. P. Bishop, and T. R. Tephly: Expressed human UGT1.4 protein catalyses the formation of quaternary ammonium glucuronides. Drug Metab. Dispos. 23, 299-302 (1995).