Journal
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
Volume 161, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.ejps.2021.105802
Keywords
bRo5; Drug discovery; Ionization; Lipophilicity; Nonpolar environments; Zwitterion
Categories
Funding
- University of Torino
- Estonian Research Council [PRG690]
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This study characterized the ionization and lipophilicity properties of rifampicin using experimental methods in various media, finding that the neutral and cationic states of rifampicin have different impacts on its lipophilicity in different environments.
Ionization and lipophilicity in early drug discovery are commonly characterized in water and octanol/water, respectively and thus do not consider the non-polar features of the biomembrane core. This is particularly limiting for bRo5 compounds which may adapt their properties (e.g. ionization and lipophilicity) to the environment. In this paper we used experimental methods to characterize rifampicin for its ionization properties in various water/cosolvent mixtures and in pure MeCN and its lipophilicity in octanol/water and toluene/water systems. Moreover, we also measured log k?80 PLRP-S, a chromatographic index of lipophilicity in non-polar media. Results show that the existence domain of neutral rifampicin is limited compared to the zwitterion, but the lipophilic cationic species is extremely relevant in non-polar environments.
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