Characterization of the solubility and solid-state properties of saccharin salts of fluoroquinolones

✍ Scribed by Romañuk, Carolina B. (author);Manzo, Ruben H. (author);Linck, Yamila Garro (author);Chattah, Ana K. (author);Monti, Gustavo A. (author);Olivera, Maria E. (author)

• Publisher: John Wiley and Sons Inc.
• Year: 2009
• Tongue: English
• Weight: 424 KB
• Volume: 98
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.21688

✦ Synopsis

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.