Identification of modified atropaldehyde mercapturic acids in rat and human urine after felbamate administration

Chemical Research in Toxicology

Volumn 10, Issue 4, 1997, Pages 457-462

  Thompson, Charles D ^a   Gulden, Pamela H ^a   Macdonald, Timothy L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; ALDEHYDE; DRUG METABOLITE; FELBAMATE; GLUTATHIONE;

ADOLESCENT; ADULT; ARTICLE; DRUG CONJUGATION; DRUG METABOLISM; DRUG TRANSFORMATION; HUMAN; MALE; MASS SPECTROMETRY; NONHUMAN; NORMAL HUMAN; ORAL DRUG ADMINISTRATION; RAT; REDUCTION; URINALYSIS;

ACETYLCYSTEINE; ADULT; ANIMALS; ANTICONVULSANTS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; PROPYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 0030975561     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960205e     Document Type: Article

References (19)

1. Fraser, A. D. (1996) New drugs for the treatment of epilepsy. Clin. Biochem. 29, 97-110.
2. Leppik, I. E. (1996) Felbamate. In The Treatment of Epilepsy (Shorvon, S., Dreifuss, F., Fish, D., and Thomas, D., Eds.) pp 421-428, Blackwell Science, New York.
3. Swinyard, E. A., Sofia, R. D., and Kupferberg, H. J. (1986) Comparative anticonvulsant activity and neurotoxicity of felbamate and four prototype antiepileptic drugs in mice and rats. Epilepsia 27, 27-34.
4. Pennell, P. B., Ogaily, M. S., and Macdonald, R. L. (1995) Aplastic anemia in a patient receiving felbamate for complex partial seizures. Neurology 45, 456-460.
5. O'Neil, M. G., Perdun, C. S., Wilson, M. D., McGown, S. T., and Patel, S. (1996) Felbamate-associated fatal acute hepatic necrosis. Neurology 46, 1457-1459.
6. Nightingale, S. L. (1994) From the food and drug administration. Recommendation to immediately withdraw patients from treatment with felbamate. J. Am. Med. Assoc. 272, 995.
7. Thompson, C. D., Kinter, M. T., and Macdonald, T. L. (1996) Synthesis and in vitro reactivity of 3-carbamoyl-2-phenylpropionaldehyde and 2-phenylpropenal: Putative reactive metabolites of felbamate. Chem. Res. Toxicol. 9, 1225-1229.
8. Yang, J. T., Adusumalli, V. E., Wong, K. K., Kucharczyk, N., and Sofia, R. D. (1991) Felbamate metabolism in the rat, rabbit, and dog. Drug Metab. Dispos. 19, 1126-1134.
9. Adusumalli, V. E., Choi, Y. M., Romanyshyn, L. A., Sparadoski, R. E., Wichmann, J. K., Wong K. K., Kucharczyk, N., and Sofia, R. D. (1993) Isolation and identification of 3-carbamoyloxy-2-phenylpropionic acid as a major human urinary metabolite of felbamate. Drug Metab. Dispos. 21, 710-716.
10. Vermeulen, N. P. E. (1989) Analysis of mercapturic acids as a tool in biotransformation, biomonitoring and toxicological studies. Trends Pharmacol. Sci. 10, 177-181.
11. Dalcanale, E., and Montanari, F. (1986) Selective oxidation of aldehydes to carboxylic acids with sodium chlorite-hydrogen peroxide. J. Org. Chem. 51, 567-569.
12. Brown, H. C., Narasimhan, S., and Choi, Y. M. (1982) Selective reductions. 30. Effect of cation and solvent on the reactivity of saline borohydrides for reduction of carboxylic esters. Improved procedures for the conversion of esters to alchohols by metal borohydrides. J. Org. Chem. 47, 4702-4708.
13. Gulden, P. H., Fischer, P., III, Sherman, N. E., Wang, W., Engelhard, V. H., Shabanowitz, J., Hunt, D. F., and Pamer, E. G. (1996) A listeria monocytogenes pentapeptide is presented to cytolytic T lymphocytes by the H2-M3 MHC class 1b molecule. Immunity 5, 73-79.
14. Fraiser, L. H., Kanekal, S., Kehrer, J. P. (1991) Cyclophosphamide toxicity characterising and avoiding the problem. Drugs 42, 781-795.
15. Bourdi, M., Chen, W., Peter, R. M., Martin, J. L., Buters, T. M., Nelson, S. D., and Pohl, L. R. (1996) Human cytochrome P450 2E1 is a major autoantigen associated with halothane hepatitis. Chem. Res. Toxicol. 9, 1159-1166.
16. Uetrecht, J. P. (1996) Drug-induced lupus: possible mechanisms and their implications for prediction of which new drugs may induce lupus. Exp. Opin. Invest. Drugs 5, 851-860.
17. 7-Guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane. Biochemistry 25, 2192-2198.
18. Monks, T. J., Anders, M. W., Dekant, W., Stevens, J. L., Lau, S. S., van Bladeren, P. J. (1990) Glutathione conjugate mediated toxicities. Toxicol. Appl. Pharmacol. 106, 1-19.
19. Ramu, K., Fraiser, L. H., Mamiya, B., Ahmed, T., and Kehrer, J. P. (1995) Acrolein mercapturates: synthesis, characterization, and assessment of their role in the bladder toxicity of cyclophosphamide. Chem Res. Toxicol. 8, 515-524.