Optimizing Solubility and Permeability of a Biopharmaceutics Classification System (BCS) Class 4 Antibiotic Drug Using Lipophilic Fragments Disturbing the Crystal Lattice
2013 (English)In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 56, no 6, 2690-2694 p.Article in journal (Refereed) Published
Esterification was used to simultaneously increase solubility and permeability of ciprofloxacin, a biopharmaceutics classification system (BCS) class 4 drug (low solubility/low permeability) with solid-state limited solubility. Molecular flexibility was increased to disturb the crystal lattice, lower the melting point, and thereby improve the solubility, whereas lipophilicity was increased to enhance the intestinal permeability. These structural changes resulted in BCS class 1 analogues (high solubility/high permeability) emphasizing that simple medicinal chemistry may improve both these properties.
Place, publisher, year, edition, pages
2013. Vol. 56, no 6, 2690-2694 p.
IdentifiersURN: urn:nbn:se:uu:diva-199465DOI: 10.1021/jm301721eISI: 000317032200042OAI: oai:DiVA.org:uu-199465DiVA: diva2:620304