From a binary salt to salt co-crystals of antibacterial agent lomefloxacin with improved solubility and bioavailability

The cocrystallization of lomefloxacin (Lf) with barbituric acid (HBA) and/or isophthalic acid (H(2)ip) leads to novel binary and ternary salts via hydrogenbonding recognition. X-ray single-crystal diffraction analyses show that zwitterionic lomefloxacin can adjust itself to fulfill a different supramolecular array in either binary salts or ternary salt co-crystals, formulated as [HLf]center dot[Hip]center dot H2O (1), [HLf]center dot[BA]center dot[HBA]center dot H2O (2) and [HLf]center dot[BA]center dot[H(2)ip]center dot CH3OH center dot H2O (3). These pharmaceutical agents present uniform charge-assisted hydrogen-bonding networks between HLf cations and acidic coformers with the lattice capturing water molecules. Structural comparison of (2) and (3) indicated that a delicate balance of geometries and hydrogenbonding partners is required for stacking to favor the formation of ternary salt co-crystals. Cocrystallization was able to overcome the water insolubility of lomefloxacin. Both the salt co-crystals display enhanced solubility and better pharmaceutical applicability.