Multinuclear solid state nmr investigation of of two polymorphic forms of Ciprofloxacin-saccharinate.

Y. GARRO LINCK; A. K. CHATTAH; R. GRAF; C. B. ROMAÑUK; M. E. OLIVERA; R. H. MANZO; H. W. SPIESS; G. A. MONTI

Angra Dos Reis

Congreso; AUREMN 2011 (13th NMR Users Meeting); 2011

AUREMN

Multicomponent crystalline pharmaceutical solids, as for example complexes or salts, are usually developed to improve the pharmaceutical performance of a single organic molecule in terms of solubility, stability, bioavailability and/or organoleptic properties.(1,2) On the other hand, the phenomenon of polymorphism and its influence on the chemical and physical properties of molecular crystals is well known.(3) This is especially true for pharmaceutical compounds, where polymorphic changes in the drugs can lead to significant effects on bioavailability. The present multicomponent compound is a new ciprofloxacin saccharinate recently obtained.(4) Ciprofloxacin (CIP), is a widely prescribed, broad-spectrum oral fluoroquinolone antibiotic approved for the treatment of several types of infections. Interestingly, ciprofloxacin saccharinate (CIP-SAC) can exist in two different polymorphic forms, CIP-SAC (I) and CIP-SAC (II).(5) 1H NMR spectra under very fast MAS were recorded for the three samples. 1 R. D. B. Walsh et al.; J. Chem. Commun. 2003, 186. 2 J. F. Remenar et al.; J. Am. Chem. Soc. 2003, 125, 8456. 3 Polymorphism in the Pharmaceutical Industry, Edited by R. Hilfiker, Wiley-VCH, 2006 4 C. B. Romañuk et al.; J. Pharm. Sci. 2009, 98, 3788. 5 C.B. Romañuk et al.; Int. J. of Pharmaceutics 2010, 391, 197.