Detection of 2-hydroxyiminostilbene in the urine of patients taking carbamazepine and its oxidation to a reactive iminoquinone intermediate

Journal of Pharmacology and Experimental Therapeutics

Volumn 288, Issue 1, 1999, Pages 51-56

  Ju, C ^a   Uetrecht, J P ^a,b   Van Koppen, Chris J ^c  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY HOSPITAL ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYCARBAMAZEPINE; 2 HYDROXYIMINOSTILBENE; CARBAMAZEPINE; DRUG METABOLITE; UNCLASSIFIED DRUG;

AGED; ANTICONVULSANT THERAPY; ARTICLE; CASE REPORT; CONVULSION; DRUG INDUCED DISEASE; DRUG METABOLISM; DRUG OXIDATION; DRUG URINE LEVEL; HUMAN; MALE; PRIORITY JOURNAL; TISSUE SPECIFICITY;

EID: 0032912536     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Amore BM, Kalhorn TF, Skiles GL, Hunter AP, Bennett GD, Finnell RH, Nelson SD and Slattery JT (1997) Characterization of carbamazepine metabolism in a mouse model of carbamazepine teratogenicity. Drug Metab Dispos 25:953-962.
2. Askmark H, and Wiholm B (1990) Epidemiology of adverse reactions to carbamazepine as seen in a spontaneous reporting system. Acts Neurol Scand 81:131-140.
3. Cereghino JJ, Brock JT, Van Meter JC, Penry JK, Smith LD and White BG (1974) Carbamazepine for epilepsy. Neurology 24:401-410.
4. Cereghino JJ, Van Meter JC, Brock JT, Penry JK, Smith LD and White BG (1973) Preliminary observations of serum carbamazepine concentration in epileptic patients. Neurology 23:357-366.
5. Chang VHT (1983) Synthesis of 2-hydroxycarbamazepine: a metabolite of carbamazepine. J Heterocyclic Chem 20:237-238.
6. Crill WE (1973) Drugs 5 years later: carbamazepine. Ann Intern Med 79:844-847.
7. Durelli L, Massazza U and Cavallo R (1989) Carbamazepine toxicity and poisoning: incidence, clinical features and management. Med Tax Adv Drug Exp 4:95-107.
8. Eichelbaum M, Jensen C, von Sassen W, Bertilsson L and Tomson T (1984) In vivo and in vitro biotransformation of carbamazepine in man and rat, in Metabolism of Antiepileptic Drugs. (Levy RH, Pitlick WH, Eichelbaum M and Meijer J eds) pp 27-33, Raven Press, New York.
9. Gaedigk A, Spielberg SP and Grant DM (1994) Characterization of the microsomal epoxide hydrolase gene in patients with anticonvulsant adverse drug reactions. Pharmacogenetics 4:142-153.
10. Gerson WT, Fine DG, Spielberg SP and Sensenbrenner LL (1983) Anticonvulsant-induced aplastic anemia: increased susceptibility to toxic drug metabolites in vitro. Blood 61:889-893.
11. Gram L and Jensen PK (1989) Carbamazepine toxicity., in Antiepileptic drugs. (Levy R, Mattson R, Meldrum B, Penry JK and Dreifuss FE eds) pp 555-565, Raven Press, New York.
12. Green VJ, Pirmohamed M, Ketteringham NR, Gaedigk A, Grata DM, Boxer M, Burchell B and Park BK (1995) Genetic analysis of microsomal epoxide hydrolase in patients with carbamazepine hypersensitivity. Biochem Pharmacol 50:1353-1359.
13. Hanzlik RP, Hogberg K and Judson CM (1984) Microsomal hydroxylation of specifically deuterated monosubstituted benzenes: evidence for direct aromatic hydroxylation. Biochemistry 23:3048-3055.
14. Haque KE and Proctor GR (1968) Dibenzo[b, f] azepine-2-one. Chem Commun 22:1412-1413.
15. Horowitz S, Patwardhan B and Marcell E (1988) Hepatotoxic reactions associated with carbamazepine therapy. Epilepsia 29:149-154.
16. Islam I and Skibo EB (1991) Structure-activity studies of antitumor agents based on pyrrolo [1,2-a] benzimidazoles: new reductive alkylating DNA cleaving agents. J Med Chem 34:2954-2961.
17. Ivanetich KM, Ziman MR and Bradshaw JJ (1982) 1,1,1-Trichloropropene-2,3-oxide; an alternate mechanism for its inhibition of cytochrome p-450. Res Commun Chem Path Pharmacol 35:111-119.
18. Kendall PM, Johnson JV and Cook CE (1979) Synthetic route to an aromatic analogue of strigol. J Org Chem 44:1421-1424.
19. Larrey D, Berson A, Habersetzer F, Tinel M, Castot A, Babany G, Letteron P, Frenneaux E, Loeper J, Dansette P and Pessayre D (1989) Genetic predisposition to drug hepatotoxicity: role in hepatitis caused by amineprine, a tricyclic antidepressant. Hepatology 10:168-173.
20. Lertratanangkoon K and Horning MG (1982) Metabolism of carbamazepine. Drug Metab Dispos 10:1-10.
21. Lillibridge JH, Amore BM, Slattery JT, Kalhorn TF, Nelson SD, Finnell RH and Bennett GD (1996) Protein-reactive metabolites of carbamazepine in mouse liver microsomes. Drug Metab Dispos 24:509-514.
22. Madden S, Maggs JL and Park BK (1996) Bioactivation of carbamazepine in the rats in vivo: evidence for the formation of reactive arene oxide(s). Drug Metab Dispos 224:469-479.
23. Maggs JL, Pirmohamed M, Kitteringham NR and Park BK (1997) Characterization of the metabolites of carbamazepine in patient urine by liquid chromatography/ mass spectrometry. Drug Metab Dispos 25:275-280.
24. Pellock JM (1987) Carbamazepine side effects in children and adults. Epilepsia 28:S64-S70.
25. Pirmohamed M, Kitteringham NR, Guenthner TM, Breckenridge AM and Park BK (1992) An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro. Biochem Pharmacol 43:1675-1682.
26. Regnaud L, Sirios G and Chakrabarti S (1988) 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.
27. Rietjens IM, den Besten C, Hanzlik RP and van Bladern PJ (1997) Cytochrome P450-catalyzed oxidations of halobenzene. Chem Res Toxicol 10:629-635.
28. Riley RJ, Kitteringham NR and Park BK (1989) Structural requirements for bioactivation of anticonvulsants to cytotoxic metabolism in vitro. BrJ Clin Pharmacol 28:482-487.
29. Shear NH, Spielberg SP, Cannon M and Miller M (1988) Anticonvulsant hypersensitivity syndrome: in vitro risk assessment. J Clin Invest 82:1826-1832.
30. Spielberg SP, Gordon GB, Blake DA, Mellits ED and Bross DS (1981) Anticonvulsant toxicity in vitro: possible role of arene oxides. J Pharmacol Exp Ther 217:386-389.
31. Uetrecht JP (1996) Reactive metabolites and agranulocytosis. Eur J Haematol 57: S83-S88.