Abstract
AbstractTo improve the solubility of the fluoroquinolone drug gatifloxacin (GAT), a pharmaceutical salt of GAT with 2,3‐dihydroxybenzoic acid (2,3‐HBA) is designed, synthesized, and characterized. This work is based on previous research into the synthesis of the pharmaceutical salts/cocrystals of fluoroquinolones. A comprehensive assessment of the crystal structure and the molecular electrostatic potential, as well as a Hirshfeld surface analysis, revealed that the H protons of the carboxylic groups in 2,3‐HBA are transferred to the N of the GAT piperazine ring. This results in the ionization of GAT to form charge‐assisted hydrogen bonds (CAHBs) and the construction of a crystal structure. It is precisely the conversion of GAT from a neutral state to an ionic state that results in a significant increase in the solubility of GAT‐2,3‐HBA. Surprisingly, in the process of increasing its solubility, the hygroscopic stability and the antibacterial activities in vitro of GAT‐2,3‐HBA is also superior to GAT. In this study, a pharmaceutical salt of gatifloxacin with targeted structures and desired properties, based on CAHBs is successfully designed and synthesized. These encouraging results suggest that CAHBs play a crucial role in adjusting molecular packing through a co‐crystallization strategy, thus improving the physicochemical properties of fluoroquinolones.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
