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Towards Understanding the Phenytoin-like Antiepileptic Effect of Cannabidiol and Related Phytocannabinoid Metabolites: Insights from Molecular Modeling

preprint
revised on 02.01.2019 and posted on 02.01.2019 by Istvan Ujvary, Antal Lopata
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.

Funding

No funding was received

History

Email Address of Submitting Author

ujvary@iif.hu

Institution

iKem BT

Country

Hungary

ORCID For Submitting Author

0000-0003-2588-5485

Declaration of Conflict of Interest

There is no competing financial interest.

Version Notes

Version 2.0

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