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Abstract
Cannabidiol
(CBD), a nonpsychotropic constituent of Cannabis
sativa, has recently been approved by the US FDA for the treatment
of certain forms of pediatric epilepsy. The
mechanism by which CBD exerts its antiepileptic effects, however, is not
known. Herein we describe the results of molecular modeling studies
comparing the
stereoelectronic properties of phenytoin (PHT) with those of CBD and its
carboxylic acid
metabolite, as well as of 7-hydroxycannabidivarin. Also, the
cyclohexenecarboxylic acid core of
7-COOH-CBD perfectly mimics the unsaturated bioactive metabolite
of the commonly used antiepileptic valproic acid was also noted. We propose that C–7
oxidized phytocannabinoid metabolites are involved in the phenytoin-like
anticonvulsant effects of the parent phytocannabinoid drugs.
