Ciprofloxacin salt and salt co-crystal with di-hydroxy-benzoic acids

Yuda Prasetya Nugraha; Haruki Sugiyama; Hidehiro Uekusa

doi:10.1107/S2056989022001177

Ciprofloxacin salt and salt co-crystal with di-hydroxy-benzoic acids

Acta Crystallogr E Crystallogr Commun. 2022 Feb 3;78(Pt 3):259-263. doi: 10.1107/S2056989022001177. eCollection 2022 Feb 1.

Authors

Yuda Prasetya Nugraha¹, Haruki Sugiyama^{2

3}, Hidehiro Uekusa⁴

Affiliations

¹ Department of Pharmaceutics, School of Pharmacy, Bandung Institute of Technology, Bandung 40132, Indonesia.
² Research and Education Center for Natural Sciences, Keio University, Hiyoshi, 4-1-1, Kohoku, Yokohama 223-8521, Japan.
³ Department of Life and Coordination-Complex Molecular Science, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan.
⁴ Department of Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8551, Japan.

Abstract

The crystal structure of two multi-component crystals of ciprofloxacin [systematic name: 1-cyclo-propyl-6-fluoro-4-oxo-7-(piperazin-1-yl)quinoline-3-carb--oxy-lic acid], a fluoro-quinolone anti-biotic, namely, ciprofloxacin 2,6-di-hydroxy-benzoate salt, C₁₇H₁₉FN₃O₃ ⁺·C₇H₅O₄ ^-, (I), and ciprofloxacin hydro-chloride-3,5-di-hydroxy-benzoic-water (1/1/1), C₁₇H₁₉FN₃O₃ ⁺·Cl^-·C₇H₆O₄·H₂O, (II), were determined. In (I) and (II), the ciprofloxacin cations are connected via head-to-tail N-H⋯O hydrogen bonding. Both structures show an alternating layered arrangement between ciprofloxacin and di-hydroxy-benzoic acid.

Keywords: antibiotic; ciprofloxacin; crystal structure; dihydroxybenzoic acid; fluoroquinolone; salt co-crystal.