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Preparation and characterization of amorphous ciprofloxacin-amino acid salts

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Show simple item record Mesallati, Hanah Conroy, Daryl Hudson, Sarah P. Tajber, Lidia 2017-10-31T16:16:34Z 2017
dc.description peer-reviewed en_US
dc.description.abstract The amorphization of the poorly soluble drug ciprofloxacin (CIP) may be facilitated by the use of a suitable stabilizer. In this study seven amino acids, with various side chain properties, were evaluated in this regard. Solid dispersions were prepared by ball milling 1:1 molar ratios of CIP with the amino acids, and their solid-state and pharmaceutical properties were then examined. Fully X-ray amorphous solid dispersions were obtained with aspartic acid, glutamic acid, cysteine and arginine. In each case, evidence of salt formation between the drug and amino acids was found via Fourier transform infrared spectroscopy and solid-state nuclear magnetic resonance. In contrast, semi-crystalline solid dispersions were obtained with serine, alanine and glycine. The glass transition temperatures of the amorphous salts were significantly higher than those of the starting materials, and they remained fully X-ray amorphous during long-term stability studies. Significant improvements in the solubility of CIP were also observed with the amorphous salts in water and simulated biological fluids, over and above that of the corresponding physical mixtures. In permeability studies on the other hand, the amorphous aspartate and glutamate salts were found to be less permeable than the pure drug, whereas formulation as an amorphous salt containing cysteine or arginine increased the permeability of CIP. Therefore, while amorphous salt formation with amino acids appears to be a suitable means of improving the thermal stability and solubility of CIP, in some cases this is associated with a decrease in permeability. en_US
dc.language.iso eng en_US
dc.publisher Elsevier en_US
dc.relation.ispartofseries European Journal of Pharmaceutics and Biopharmaceutics;121, pp. 73-89
dc.rights This is the author’s version of a work that was accepted for publication inEuropean Journal of Pharmaceutics and Biopharmaceutics . Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in European Journal of Pharmaceutics and Biopharmaceutics, 2017, 121, pp. 73-89, en_US
dc.subject ciprofloxacin en_US
dc.subject amorphous salt en_US
dc.subject amino acid en_US
dc.subject ball milling en_US
dc.subject stability en_US
dc.subject solubility en_US
dc.subject permeability en_US
dc.title Preparation and characterization of amorphous ciprofloxacin-amino acid salts en_US
dc.type info:eu-repo/semantics/article en_US
dc.type.supercollection all_ul_research en_US
dc.type.supercollection ul_published_reviewed en_US
dc.identifier.doi 10.1016/j.ejpb.2017.09.009
dc.contributor.sponsor SFI en_US
dc.relation.projectid 12/RC/2275 en_US 2018-09-15
dc.embargo.terms 2018-09-15 en_US
dc.rights.accessrights info:eu-repo/semantics/embargoedAccess en_US
dc.internal.rssid 2729372

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