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Evaluation of the Membrane Permeability (PAMPA and Skin) of Benzimidazoles with Potential Cannabinoid Activity and their Relation with the Biopharmaceutics Classification System (BCS)

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Abstract

The permeability of five benzimidazole derivates with potential cannabinoid activity was determined in two models of membranes, parallel artificial membrane permeability assay (PAMPA) and skin, in order to study the relationship of the physicochemical properties of the molecules and characteristics of the membranes with the permeability defined by the Biopharmaceutics Classification System. It was established that the PAMPA intestinal absorption method is a good predictor for classifying these molecules as very permeable, independent of their thermodynamic solubility, if and only if these have a Log P oct value <3.0. In contrast, transdermal permeability is conditioned on the solubility of the molecule so that it can only serve as a model for classifying the permeability of molecules that possess high solubility (class I: high solubility, high permeability; class III: high solubility, low permeability).

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Acknowledgments

This work was supported by the Faculty of Chemistry of the Pontificia Universidad Católica de Chile and FONDECYT (grant 1100493).

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Authors and Affiliations

  1. Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Vicuña Mackenna, 4860, Santiago, Chile

    M. Javiera Alvarez-Figueroa, C. David Pessoa-Mahana, M. Elisa Palavecino-González, Jaime Mella-Raipán, Cristián Espinosa-Bustos & Manuel E. Lagos-Muñoz

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  1. M. Javiera Alvarez-Figueroa
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  2. C. David Pessoa-Mahana
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  3. M. Elisa Palavecino-González
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  5. Cristián Espinosa-Bustos
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  6. Manuel E. Lagos-Muñoz
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Correspondence to M. Javiera Alvarez-Figueroa.

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Alvarez-Figueroa, M.J., Pessoa-Mahana, C.D., Palavecino-González, M.E. et al. Evaluation of the Membrane Permeability (PAMPA and Skin) of Benzimidazoles with Potential Cannabinoid Activity and their Relation with the Biopharmaceutics Classification System (BCS). AAPS PharmSciTech 12, 573–578 (2011). https://doi.org/10.1208/s12249-011-9622-1

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  • DOI: https://doi.org/10.1208/s12249-011-9622-1

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