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- W2149758244 abstract "DL-3-hydroxy-3-phenylpentanamide (DL-HEPP) is an anticonvulsant with a broad profile of activity. In order to study if there exists differences in biological activity between its enantiomers, we resolved the racemate from the (-) brucine and (-) 1-phenylethylamine salts of the acids. The optically active acids were then esterified with diazomethane and reacted with ammonia to give (+)-3-hydroxy-3-phenylpentanamide ((+)-HEPP) and (-)-HEPP. The enantiomeric purity of the amides was determined using proton magnetic resonance in the presence of europium tris-[3-(trifluoromethylhydroxymethylene)-(+)camphorate] and chiral high performance liquid chromatography. Optical purity of the amides was greater than 99% enantiomeric excess, impurities were not detected. Pharmacologically, DL-HEPP and its enantiomers have a similar significant anticonvulsant activity at peak drug effect against pentylenetetrazol-induced seizures, but a variation in time between the enantiomers was found with the anticonvulsant activity. In the rotarod ataxia test, the neurotoxicity of the enantiomers of DL-HEPP was also similar. The therapeutic indices of DL-HEPP and its enantiomers against the seizures induced by pentylenetrazol were better than valproate, an antiepileptic widely used in clinics. Key words: Anticonvulsants, DL-3-hydroxy-3-phenylpentanamide enantiomers, DL-HEPP, resolution, (-) HEPP, (+) HEPP, valproate." @default.
- W2149758244 created "2016-06-24" @default.
- W2149758244 creator A5017152384 @default.
- W2149758244 date "2013-09-15" @default.
- W2149758244 modified "2023-10-16" @default.
- W2149758244 title "Anticonvulsant activity and neurotoxicity of the enantiomers of DL-HEPP" @default.
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- W2149758244 doi "https://doi.org/10.5897/ajpp2013.3578" @default.
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