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Issue 14, 2012
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Tailoring aqueous solubility of a highly soluble compound viacocrystallization: effect of coformer ionization, pHmax and solute–solvent interactions

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Abstract

Cocrystals of a nonionizable, water soluble compound (gababentin lactam (GBPL)) with less soluble coformers, are shown to be 2 to 17 times less soluble than GBPL. Cocrystals of GBPL with gentisic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid and fumaric acid are characterized by carboxylic acid---amide hydrogen bonds between coformer and GBPL, consistent with a previously reported structure of a benzoic acid cocrystal. The lattice and solvation contributions to cocrystal aqueous solubility were evaluated and solvation was found to be the main contribution to solubilization. Cocrystals exhibited pH-dependent solubility and pHmax, both of which are described by coformer pKa and cocrystal Ksp values. These findings have important implications for the characterization and selection of cocrystals for desired drug delivery behavior.

Graphical abstract: Tailoring aqueous solubility of a highly soluble compound via cocrystallization: effect of coformer ionization, pHmax and solute–solvent interactions

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Article information


Submitted
02 Dec 2011
Accepted
29 Mar 2012
First published
21 May 2012

CrystEngComm, 2012,14, 4801-4811
Article type
Paper

Tailoring aqueous solubility of a highly soluble compound via cocrystallization: effect of coformer ionization, pHmax and solute–solvent interactions

C. Maheshwari, V. André, S. Reddy, L. Roy, T. Duarte and N. Rodríguez-Hornedo, CrystEngComm, 2012, 14, 4801
DOI: 10.1039/C2CE06615G

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