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Ciprofloxacin salts with benzoic acid derivatives: structural aspects, solid-state properties and solubility performance

Abstract

In this work, three new pharmaceutical salts of ciprofloxacin with the selected derivatives of benzoic acid, namely 4-hydroxybenzoic acid, 4-aminobenzoic acid and gallic acid, were obtained and systematically investigated by several solid-state analytical techniques. In situ Raman spectroscopy was applied to elucidate the alternative pathways of the salts’ formation under mechanochemical conditions. A crystal structure analysis and a CSD survey allowed us to establish a distinct supramolecular motive formed by the infinite columnar stacks of the ciprofloxacin dimers arranged in the “head-to-tail” manner. An alternative “head-to-head” packing arrangement was only observed in the crystal of ciprofloxacin salt with 4-aminobenzoic acid. In addition, the pH-solubility behavior of the solid forms was thoroughly investigated. Furthermore, a distinct structure-property relationship between the specific features of the supramolecular organization of the salts and their solubility was observed and discussed

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Supplementary files

Article information


Submitted
04 Apr 2020
Accepted
13 May 2020
First published
14 May 2020

CrystEngComm, 2020, Accepted Manuscript
Article type
Paper

Ciprofloxacin salts with benzoic acid derivatives: structural aspects, solid-state properties and solubility performance

A. O. Surov, N. Vasilev, A. P. Voronin, C. Andrei, F. Emmerling and G. L. Perlovich, CrystEngComm, 2020, Accepted Manuscript , DOI: 10.1039/D0CE00514B

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