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Ciprofloxacin (CIP) can exist in two different forms: the zwitterion and the un-ionized form. While the crystal structure of each has been described independently, the ability of CIP to transform from one form to the other in the solid state has not been described. The crystal structures of un-ionized and zwitterionic CIP were therefore compared using computational methods, including their packing arrangement, hydrogen bonding, packing energy, intermolecular potentials, and highest occupied molecular orbital/lowest occupied molecular orbital energy gap. The pure amorphous form of CIP has also never been prepared or studied. Ball milling, cryomilling, and spray drying were used in this study to prepare partially and fully amorphous CIP for the first time. The physical characteristics were examined by powder X-ray diffraction, Fourier transform infrared spectroscopy, and differential scanning calorimetry. CIP proved to be very difficult to amorphize, and only spray drying in pure water resulted in a fully a...

Two Faces of Ciprofloxacin: Investigation of Proton Transfer in Solid State Transformations