title: Physicochemical properties of lomefloxacin, levofloxacin, and moxifloxacin relevant to the biopharmaceutics classification system.
abstract: The aim of this investigation was to identify the impact of physicochemical properties of three fluoroquinolones (second, third, and fourth generation) on bioavailability in relation to the Biopharmaceutics Classification System (BCS) by in silico and in vitro methods. These properties were estimated by analyzing the electrostatic potential pattern and values of the free energy of solvation as well as the distribution coefficients and true partition coefficients of the studied compounds. This study was based on theoretical quantum-chemical methods and the in vitro shake-flask technique with two immiscible phases (n-octanol and phosphate buffer) as well as the experimental potentiometric method to estimate protonation macro- and micro-constants. Properties identified in the in vitro and in silico studies were similar and indicated high lipophilic properties of the studied molecules as well as their good solubility in a polar medium. It appears that both the theoretical methods and simple in vitro studies are useful tools for predicting the bioavailability of medicinal substances based on the BCS principles.
authors.forename: Ewa
authors.initials: E
authors.lastname: Kłosińska-Szmurło
authors.forename: Monika
authors.initials: M
authors.lastname: Grudzień
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Betlejewska-Kielak
authors.forename: Franciszek
authors.initials: F
authors.lastname: Pluciński
authors.forename: Joanna
authors.initials: J
authors.lastname: Biernacka
authors.forename: Aleksander Paweł
authors.initials: AP
authors.lastname: Mazurek
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry; D001702:Biopharmaceutics / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D004563:Electrochemistry / Q000379:methods; D024841:Fluoroquinolones / Q000737:chemistry*; D041981:Gastrointestinal Tract / Q000187:drug effects; D006801:Humans; D006863:Hydrogen-Ion Concentration; D064704:Levofloxacin / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D000077266:Moxifloxacin; D010539:Permeability; D010710:Phosphates / Q000737:chemistry; D011199:Potentiometry; D011522:Protons; D011789:Quantum Theory; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D055672:Static Electricity; D013696:Temperature
chemical_list: D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D010710:Phosphates; D011522:Protons; D012997:Solvents; D064704:Levofloxacin; C053091:lomefloxacin; D000077266:Moxifloxacin