title: Characterization of the solubility and solid-state properties of saccharin salts of fluoroquinolones.
abstract: Saccharinates salts of the fluoroquinolone antibiotics norfloxacin, ciprofloxacin, ofloxacin, and enrofloxacin were obtained as pure crystalline anhydrous solids with sweet taste. The products were characterized by one- ((13)C) and two-dimensional ((1)H-(13)C) dimensions solid state Nuclear Magnetic Resonance and infrared spectroscopy showing ionic interactions between the saccharine amide and the fluoroquinolone piperazine. Several intermolecular bindings were also identified. Thermal behavior and powder X-ray diffraction provided complementary evidences of salt formation. The series of products showed improved properties with respect to water solubility. A solubility model was developed. These salts would be a good way forward to developing more suitable formulations of these APIs.
authors.affiliation: Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
authors.forename: Carolina B
authors.initials: CB
authors.lastname: Romañuk
authors.forename: Ruben H
authors.initials: RH
authors.lastname: Manzo
authors.forename: Yamila Garro
authors.initials: YG
authors.lastname: Linck
authors.forename: Ana K
authors.initials: AK
authors.lastname: Chattah
authors.forename: Gustavo A
authors.initials: GA
authors.lastname: Monti
authors.forename: Maria E
authors.initials: ME
authors.lastname: Olivera
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002152:Calorimetry, Differential Scanning; D003460:Crystallization; D004055:Differential Thermal Analysis; D024841:Fluoroquinolones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012439:Saccharin / Q000737:chemistry*; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013818:Thermogravimetry; D014961:X-Ray Diffraction
chemical_list: D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D012439:Saccharin