Synthesis and in vitro reactivity of 3-carbamoyl-2- phenylpropionaldehyde and 2-phenylpropenal: Putative reactive metabolites of felbamate

Chemical Research in Toxicology

Volumn 9, Issue 8, 1996, Pages 1225-1229

  Thompson, Charles D ^a   Kinter, Michael T ^a   Macdonald, Timothy L ^a,b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b Chemistry Department   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYNONENAL; ACROLEIN; DRUG METABOLITE; FELBAMATE; GLUTATHIONE;

ALLERGENICITY; ANIMAL CELL; ARTICLE; CHO CELL; CONJUGATION; CONTROLLED STUDY; CYCLIZATION; DRUG CYTOTOXICITY; DRUG HALF LIFE; DRUG STABILITY; NONHUMAN;

ALDEHYDES; ANIMALS; ANTICONVULSANTS; CELL SURVIVAL; CELLS, CULTURED; CRICETINAE; FIBROBLASTS; GUINEA PIGS; HALF-LIFE; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; PROPYLENE GLYCOLS;

ANIMALIA;

EID: 0029849184     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9601566     Document Type: Article

References (22)

1. The Felbamate Study Group in Lennox-Gastaut Syndrome. (1993) Efficacy of felbamate in childhood epileptic encephalopathy (Lennox-Gastaut syndrome). N. Engl. J. Med. 328, 29-33.
2. Burdette, D. E., and Sackellares, J. C. (1994) Felbamate pharmacology and use in epilepsy. Clin. Neuropharmacol. 17, 389-402.
3. Fraser, A. D. (1996) New drugs for the treatment of epilepsy. Clin. Biochem. 29, 97-110.
4. 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.
5. 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.
6. Sachdeo, R., Kramer, L. D., Rosenberg A., and Sachdeo, S. (1992) Felbamate monotherapy: controlled trial in patients with partial onset seizures. Ann. Neurol. 32, 386-392.
7. Bourgeois, B., Leppik, I. E., Sackellares, J. C., Laxer, K., Lesser, R., Messenheimer, J. A., Kramer, L. D., Kamin, M., and Rosenberg, A. (1993) Felbamate: a double-blind controlled trial in patients undergoing presurgical evaluation of partial seizures. Neurology 43, 693-696.
8. Nightingale, S. L. (1994) From the food and drug administration. Recommendation to immediately withdraw patients from treatment with felbamate. JAMA, J. Am. Med. Assoc. 272, 995.
9. 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.
10. Young, N. S., and Alter, B. P. (1994) Aplastic anemia: acquired and inherited, W. B. Saunders, Philadelphia.
11. Brodie, M. J., and Pellock, J. M. (1995) Taming the brain storms: felbamate updated. Lancet 346, 918-919.
12. 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.
13. 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.
14. 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.
15. 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.
16. Grassland, I. (1981) Atropaldehyde. Org. Synth. 60, 6-10.
17. Yang, S. J., Hahn, G. M., and Bagshaw, M. A. (1966) Chromosome aberrations induced by thymidine. Cell Res. 42, 130-135.
18. Kinter, M. T., and Roberts, R. J. (1996) Glutathione consumption and glutathione peroxidase inactivation by 4-hydroxy-2-nonenal in cultured fibroblasts. Free Radical Biol. Med. 21, 457-462.
19. Spitz, D. R., Kinter, M. T., and Roberts, R. J. (1995) Contribution of increased glutathione content to mechansims of oxidative stress resistance in hydrogen peroxide resistant hamster fibroblasts. J. Cell. Phys. 165, 600-609.
20. Cory, A. H., Owen, T. C., Barltrop, J. A., and Cory, J. G. (1991) Use of an aqueous soluble tetrazolium/formazan assay for cell growth assay in culture. Cancer Commun. 3, 207-212.
21. Niwayama, S., Turk, B. E., and Liu, J. O. (1996) Potent inhibition of tumor necrosis factor-α production by tetrafluorothalidomide and tetrafluorophthalimides. J. Med. Chem. 39, 3044-3045.
22. Pohl, L. R., Kenna, J. G., Satoh, H., Christ, D. D., and Martin, J. L. (1989) Neoantigens associated with halothane hepatitis. Drug Metab. Rev. 20, 203-217.