Crystal packing arrangement, chain conformation, and physicochemical properties of gemfibrozil amine salts

Miren Ramirez, Sarah E. David, Carl H. Schwalbe, Kofi Asare-Addo, Barbara R. Conway, Peter Timmins*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Salt formation is used to optimize pharmaceutical properties for carboxylic acid drugs, but selection can often be empirical. An extended series of salts of the anti-hyperlipidaemia carboxylic acid drug gemfibrozil was prepared using a related series of amine counterions to gain a molecular insight into the impact of crystal packing arrangements on their physicochemical properties. With only a few exceptions, the salts had similar crystal packing motifs. Although there was no discernible relationship between melting point of the salt form and the aqueous solubility of the salt across the whole data set, there were trends within structurally related series of salts relating increasing melting enthalpy with increasing molecular weight of the counterion.

Original languageEnglish
Pages (from-to)3743-3750
Number of pages8
JournalCrystal Growth and Design
Volume17
Issue number7
DOIs
Publication statusPublished - 13 Jun 2017

Bibliographical note

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.cgd.7b00352

Fingerprint Dive into the research topics of 'Crystal packing arrangement, chain conformation, and physicochemical properties of gemfibrozil amine salts'. Together they form a unique fingerprint.

  • Cite this

    Ramirez, M., David, S. E., Schwalbe, C. H., Asare-Addo, K., Conway, B. R., & Timmins, P. (2017). Crystal packing arrangement, chain conformation, and physicochemical properties of gemfibrozil amine salts. Crystal Growth and Design, 17(7), 3743-3750. https://doi.org/10.1021/acs.cgd.7b00352