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Solid Forms of Ciprofloxacin Salicylate: Polymorphism, Formation Pathways, and Thermodynamic Stability

  • The crystallization of ciprofloxacin - an antibacterial fluoroquinolone compound - with salicylic acid resulted in the isolation of five distinct solid forms of the drug, namely, an anhydrous salt, two polymorphic forms of the salt monohydrate, methanol and acetonitrile solvates, and the salt-cocrystal hydrate. The salicylate salts were investigated by different analytical techniques ranging from powder and single crystal X-ray diffractometry, differential scanning calorimetry, thermogravimetric analysis, variable temperature powder X-ray diffraction, dynamic vapor sorption analysis, dissolution, and solubility investigations. Real-time in situ Raman spectroscopy was used to investigate the mechanochemical formation pathways of the different solid polymorphs of ciprofloxacin salicylate. The mechanism of the phase transformation between the crystalline forms was evaluated under mechanochemical conditions. It was found that the formation pathway and kinetics of the grinding processThe crystallization of ciprofloxacin - an antibacterial fluoroquinolone compound - with salicylic acid resulted in the isolation of five distinct solid forms of the drug, namely, an anhydrous salt, two polymorphic forms of the salt monohydrate, methanol and acetonitrile solvates, and the salt-cocrystal hydrate. The salicylate salts were investigated by different analytical techniques ranging from powder and single crystal X-ray diffractometry, differential scanning calorimetry, thermogravimetric analysis, variable temperature powder X-ray diffraction, dynamic vapor sorption analysis, dissolution, and solubility investigations. Real-time in situ Raman spectroscopy was used to investigate the mechanochemical formation pathways of the different solid polymorphs of ciprofloxacin salicylate. The mechanism of the phase transformation between the crystalline forms was evaluated under mechanochemical conditions. It was found that the formation pathway and kinetics of the grinding process depend on the form of the starting material and reaction conditions. The analysis of the solid-state thermal evolution of the hydrated salts revealed the two-step mechanism of dehydration process, which proceeds through a formation of the distinct intermediate crystalline products.zeige mehrzeige weniger

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Metadaten
Autor*innen:Artem O. Surov, Nikita A. Vasilev, Andrei V. Churakov, Julia StrohORCiD, Franziska EmmerlingORCiD, German L. Perlovich
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Crystal Growth & Design
Jahr der Erstveröffentlichung:2019
Organisationseinheit der BAM:6 Materialchemie
6 Materialchemie / 6.3 Strukturanalytik
Verlag:American Chemical Society
Jahrgang/Band:19
Ausgabe/Heft:5
Erste Seite:2979
Letzte Seite:2990
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Freie Schlagwörter:Ciprofloxacin; Cocrystal; DSC; Polymorphism; XRD
Themenfelder/Aktivitätsfelder der BAM:Chemie und Prozesstechnik
DOI:10.1021/acs.cgd.9b00185
ISSN:1528-7483
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:08.05.2019
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:23.05.2019
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