Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties

Abstract

Ciprofloxacin (CfH, C 17 H 18 FN 3 O 3 ) crystallizes with 2-thiobarbituric (H 2 tba) and barbituric acid (H 2 ba) in the aqueous solution to yield salt CfH 2 (Htba)·3H 2 O (1), salt cocrystal CfH 2 (Hba)(H 2 ba)·3H 2 O (2), and salt CfH 2 (Hba)·H 2 O (3). The compounds are structurally characterized by the Xray single-crystal diffraction. The numerous intermolecular hydrogen bonds N-H⋯O and O-H⋯O formed by water molecules, Htba − /Hba − and CfH 2 + ions, and H 2 ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π-π interactions in 1 to 3.The compounds have been characterized by powder X-ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C. KEYWORDS barbituric and thiobarbituric acids, ciprofloxacin, infrared spectroscopy, salt cocrystal, thermal stability, X-ray diffraction Electronic supplementary information (ESI) available.

Enhancing Dissolution Rate and Antibacterial Efficiency of Azithromycin through Drug-Drug Cocrystals with Paracetamol

“…Due to the complex FTIR spectrum of cocrystal (AZT-PCM) the unambiguous assignment of peaks is very tough task. However, attenuation, broadening and slight change in position of peaks can give a hint for Van der Waals interactions [ 49 , 50 ]. An abnormally broad peak formed in the region of 3600–3015 cm −1 indicates some new set of H-bond interactions [ 51 , 52 ], while no such peak formation is observed in the physical mixture spectrum.…”

Application of 1-Hydroxy-4,5-Dimethyl-Imidazole 3-Oxide as Coformer in Formation of Pharmaceutical Cocrystals

“…The TBA 2 and BA 3, as well as their derivatives, commonly known as barbiturates, play an important role in pharmaceutical industry because of their hypnotic, sedative, anticonvulsant, antimicrobial, anesthetic, anticancer and antitumor properties [41]. Due to the unique structure of 3 and their ability to form keto-enol tautomers, it is widely used as a valuable building block in organic synthesis and advanced materials including cocrystals [42,43].…”

Antimicrobial Activities of Highly Bioavailable Organic Salts and Ionic Liquids from Fluoroquinolones

“…The formation of organic salts based on cationic fluoroquinolones (mostly comprising ciprofloxacin (Cip), but also norfloxacin (Nor)) has been widely explored by the academic community by protonation of the drugs' amine group(s). More precisely, these fluoroquinolones have been combined with dicarboxylic acids (malonic and tartaric [31], adipic, fumaric [32] and maleic [33,34], succinic [35]), citric acid [32], saccharine [36,37] and acesulfame [36], as well as with other drugs (diflunisal and ibuprofen [38], salicylic [39] and barbituric acids [40]). Some works involve the combination of ciprofloxacin or enrofloxacin as cations and/or as anions with amino acids [41] and ionic polymers [42,43].…”