Ciprofloxacin salts with benzoic acid derivatives: structural aspects, solid-state properties and solubility performance. Issue 25 (10th June 2020)

• Record Type: Journal Article
• Authors: Surov, Artem O.; Vasilev, Nikita A.; Voronin, Alexander P.; Churakov, Andrei V.; Emmerling, Franziska; Perlovich, German L.
• Is Part Of: CrystEngComm. Volume 22:Issue 25(2020)
• Page Start: 4238
• Page End: 4249
• Publication Date: 2020-06-10
• Subjects: Crystals -- Periodicals; Crystal growth -- Periodicals; Crystallography -- Periodicals; Cristaux -- Périodiques; Cristaux -- Croissance -- Périodiques; Cristallographie -- Périodiques; 548
• DOI: 10.1039/d0ce00514b
• Languages: English
• ISSNs: 1466-8033

Abstract

Abstract : In this work, three new pharmaceutical hydrated salts of ciprofloxacin with selected derivatives of benzoic acid were obtained and systematically investigated by several solid-state analytical techniques. Abstract : In this work, three new pharmaceutical hydrated salts of ciprofloxacin with 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 solid forms' formation under mechanochemical conditions. Crystal structure analysis and a CSD survey allowed us to establish a distinct supramolecular motif formed by infinite columnar stacks of ciprofloxacin dimers arranged in the "head-to-tail" manner. An alternative "head-to-head" packing arrangement was only observed in the crystal of the hydrated 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 hydrated salts and their solubility was observed and discussed.