Preparation and Physiochemical Analysis of Novel Ciprofloxacin / Dicarboxylic Acid Salts.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
Read More Add to Saved list
  • Additional Information
    • Source:
      Publisher: Elsevier Country of Publication: United States NLM ID: 2985195R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6017 (Electronic) Linking ISSN: 00223549 NLM ISO Abbreviation: J Pharm Sci Subsets: MEDLINE
    • Publication Information:
      Publication: 2016- : New York, NY : Elsevier
      Original Publication: Easton, Pa., American Pharmaceutical Assn.
    • Subject Terms:
      Ciprofloxacin*/pharmacology ; Ciprofloxacin*/chemistry ; Salts*/chemistry; Dicarboxylic Acids/chemistry ; Calorimetry, Differential Scanning ; Solubility ; X-Ray Diffraction ; Spectroscopy, Fourier Transform Infrared
    • Abstract:
      The crystal structures of four novel dicarboxylic acid salts of ciprofloxacin (CFX) with modified physicochemical properties, prepared by mechanochemical synthesis and solvent crystallization, are reported. A series of dicarboxylic acids of increasing molecular weight was chosen, predicted to interact via a carboxylic acid:secondary amine synthon. These were succinic (SA), glutaric (GA), adipic (AA) and pimelic (PA) acids (4, 5, 6, 7 carbon atoms respectively). Characterized by single crystal and powder X-ray diffraction, Fourier-Transform Infrared Spectroscopy, thermogravimetric analysis, differential scanning calorimetry, scanning electron microscopy and aqueous solubility measurements, these salts showed distinct physicochemical properties relative to ciprofloxacin base. Searches of the Cambridge Structural Database (CSD) confirmed CFX-SA, CFX-GA, CFX-AA and CFX-PA to be novel crystal structures. Furthermore, the GA salt has substantially higher solubility than the widely available hydrochloride monohydrate salt (CFX-HCl·H 2 O). CFX-SA, CFX-GA and CFX-AA showed minimum inhibitory concentration (MIC) of 0.008 g/L and CFX-PA showed MIC of 0.004 g/L. The prepared CFX salts retained antibacterial activity exhibiting equivalent antimicrobial activity to CFX-HCl·H 2 O. These salts have positive implications for increasing the application of CFX beyond conventional oral formulations and highlight mechanochemical activation as suitable production method.
      Competing Interests: Conflict of Interest Disclosure The authors declare no conflict of interest.
      (Copyright © 2022 The Authors. Published by Elsevier Inc. All rights reserved.)
    • Contributed Indexing:
      Keywords: Ciprofloxacin; Crystalline salts; Mechanochemical activation; Single crystal; Solubility; Thermal analysis
    • Accession Number:
      5E8K9I0O4U (Ciprofloxacin)
      0 (Salts)
      0 (Dicarboxylic Acids)
    • Publication Date:
      Date Created: 20220810 Date Completed: 20221220 Latest Revision: 20230214
    • Publication Date:
      20240829
    • Accession Number:
      10.1016/j.xphs.2022.08.008
    • Accession Number:
      35948159