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


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.

Publication DOI:
Divisions: College of Health & Life Sciences > Aston Pharmacy School
Additional Information: 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
Uncontrolled Keywords: Chemistry(all),Materials Science(all),Condensed Matter Physics
Publication ISSN: 1528-7505
Last Modified: 06 May 2024 07:20
Date Deposited: 09 Aug 2017 08:25
Full Text Link:
Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2017-06-13
Accepted Date: 2017-05-30
Authors: Ramirez, Miren
David, Sarah E.
Schwalbe, Carl H.
Asare-Addo, Kofi
Conway, Barbara R.
Timmins, Peter



Version: Accepted Version

| Preview

Export / Share Citation


Additional statistics for this record