Optimizing solubility and permeability of a biopharmaceutics classification system (BCS) class 4 antibiotic drug using lipophilic fragments disturbing the crystal lattice

Ulrika Tehler, Jonas H Fagerberg, Richard Svensson, Mats Larhed, Per Artursson, Christel A S Bergström

Research output: Contribution to journalArticleResearchpeer-review

20 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)2690-2694
Number of pages5
JournalJournal of Medicinal Chemistry
Issue number6
Publication statusPublished - 28 Mar 2013
Externally publishedYes

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