Solubility and in vitro drug permeation behavior of ethenzamide cocrystals regulated in physiological pH environments

Diffusivity of a drug across biological membranes can arise not only due to membrane-based efflux mechanisms, but also due to a number of structural and interactive features. We prepared several cocrystals consisting of a BCS class-II drug, ethenzamide, combined with gentisic acid, γ-resorcylic acid...

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Bibliographic Details
Published in:CrystEngComm 2017, Vol.19 (46), p.6992-7000
Main Authors: Khatioda, Rajiv, Saikia, Basanta, Das, Pranab Jyoti, Sarma, Bipul
Format: Article
Language:English
Subjects:
Acids
Diffusivity
Dihydroxybenzoic acid
Efflux
Penetration
Physiology
Solubility
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Summary:Diffusivity of a drug across biological membranes can arise not only due to membrane-based efflux mechanisms, but also due to a number of structural and interactive features. We prepared several cocrystals consisting of a BCS class-II drug, ethenzamide, combined with gentisic acid, γ-resorcylic acid, protocatechuic acid or α-resorcylic acid, and investigated the drug⋯coformer and solute⋯solvent non-covalent interactions, which can play significant roles in understanding drug solubility and permeation behavior. The solubility and membrane diffusion behavior through a cellulose membrane were determined in different physiological pH environments, and enhanced drug absorption, release and distribution was observed in vitro . The change in the lipophilic nature manifested by the conformational adjustment of the parent drug has established a link to explain the enhanced properties that are described herein. Further, this study sheds light upon the trade-off action between solubility and diffusivity, which is crucial for the advancement of pharmaceutical science.
ISSN:1466-8033
1466-8033
DOI:10.1039/C7CE01626C