A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays

[Display omitted] •New norfloxacin-nicotinic acid cocrystal was obtained by mechanochemical method.•The cocrystal’s thermal behavior was determined by TG-DTA and DSC techniques.•The binary phase diagram was built through the DSC data determining the stoichiometry.•The cocrystal’s solid-state interac...

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Veröffentlicht in:Thermochimica acta 2020-12, Vol.694, p.178782, Article 178782
Hauptverfasser: Ferreira, Patricia Osorio, de Almeida, Amanda Cosmo, dos Santos, Éverton Carvalho, Droppa, Roosevelt, Ferreira, Fabio Furlan, Kogawa, Ana Carolina, Caires, Flávio Junior
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Sprache:eng
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Zusammenfassung:[Display omitted] •New norfloxacin-nicotinic acid cocrystal was obtained by mechanochemical method.•The cocrystal’s thermal behavior was determined by TG-DTA and DSC techniques.•The binary phase diagram was built through the DSC data determining the stoichiometry.•The cocrystal’s solid-state interactions were determined from FTIR and XRPD data.•The crystalline structure was solved from XRPD data. This work reports the mechanochemical synthesis and characterization of a cocrystal formed by norfloxacin (NOR) and nicotinic acid (NCA). The thermal analysis provided the thermal stability and appropriated stoichiometry of NOR-NCA cocrystal. In addition, the crystalline structure and the coordination sites were obtained through Fourier-transform infrared spectroscopy (FTIR) and X-ray powder diffraction (XRPD). This allowed the determination of NOR-NCA interaction in the cocrystal state: the amine group of NOR interacts simultaneously with the aromatic nitrogen and the hydroxyl of the carboxyl group of NCA. Moreover, NOR-NCA crystallized in the monoclinic crystal system, space group Pa, and Z = 4, Z’ = 2. Finally, solubility assays showed an increase of NOR solubility of 2 times in pH 6.1 buffer solution. On the other hand, the cocrystal did not show a significant change in NOR solubility in pH 3.0 buffer solution, while presented a slight decrease in pH 8.5 buffer solution, which shows a pH-dependency.
ISSN:0040-6031
1872-762X
DOI:10.1016/j.tca.2020.178782