Interaction between human serum albumin and the felbamate metabolites 4-hydroxy-5-phenyl-[1, 3] oxazinan-2-one and 2-phenylpropenal

SG Roller, CM Dieckhaus, WL Santos…

Index: Dieckhaus, Christine M.; Roller, Shane G.; Santos, Webster L.; Sofia, R. Duane; Macdonald, Timothy L. Chemical Research in Toxicology, 2001 , vol. 14, # 5 p. 511 - 516

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Citation Number: 23

Abstract

Felbamate is an anti-epileptic drug associated with hepatotoxicity and aplastic anemia. These toxicities are believed to be mediated by the formation of the reactive species 2- phenylpropenal. 4-Hydroxy-5-phenyl-[1, 3] oxazinan-2-one is a metabolic precursor for 2- phenylpropenal. 4-Hydroxy-5-phenyl-[1, 3] oxazinan-2-one exists in equilibrium with 3-oxo-2- phenylpropyl carbamate, which can undergo β-elimination to form 2-phenylpropenal. The ...