Crystal Packing Arrangement, Chain Conformation, and Physicochemical Properties of Gemfibrozil Amine Salts

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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.
LanguageEnglish
Pages3743-3750
Number of pages8
JournalCrystal Growth and Design
Volume17
Issue number7
DOIs
Publication statusPublished - 13 Jun 2017

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Gemfibrozil
Amines
Conformations
amines
Salts
salts
Crystals
crystals
Carboxylic Acids
Carboxylic acids
carboxylic acids
drugs
Pharmaceutical Preparations
Drug products
melting points
Melting point
Enthalpy
molecular weight
Melting
solubility

Cite this

Ramirez, Miren ; David, Sarah E. ; Schwalbe, Carl H. ; Asare-Addo, Kofi ; Conway, Barbara ; Timmins, Peter. / Crystal Packing Arrangement, Chain Conformation, and Physicochemical Properties of Gemfibrozil Amine Salts. In: Crystal Growth and Design. 2017 ; Vol. 17, No. 7. pp. 3743-3750.
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Crystal Packing Arrangement, Chain Conformation, and Physicochemical Properties of Gemfibrozil Amine Salts. / Ramirez, Miren; David, Sarah E.; Schwalbe, Carl H.; Asare-Addo, Kofi; Conway, Barbara; Timmins, Peter.

In: Crystal Growth and Design, Vol. 17, No. 7, 13.06.2017, p. 3743-3750.

Research output: Contribution to journalArticle

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