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

CAROLINA B. ROMAÑUK; YAMILA GARRO LINCK; ANA K. CHATTAH; GUSTAVO A. MONTI; RUBÉN H. MANZO; MARÍA E. OLIVERA

JOURNAL OF PHARMACEUTICAL SCIENCES

JOHN WILEY & SONS INC

Año: 2009 vol. 98 p. 3788 - 3801

0022-3549

Saccharinates salts of the fluoroquinolone antibiotics norfloxacin, ciprofloxacin,ofloxacin, and enrofloxacin were obtained as pure crystalline anhydrous solidswith sweet taste. The products were characterized by one- (13C) and two-dimensional(1H-13C) 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 behaviorand 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.