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Title: Lipophilicity of amphoteric and zwitterionic compounds: a comparative study of determination methods
Author: Ràfols Llach, Clara
Subirats i Vila, Xavier
Rubio, Javier
Rosés Pascual, Martí
Bosch, Elisabeth
Keywords: Lipofília
Química farmacèutica
Pharmaceutical chemistry
Issue Date: 10-Oct-2016
Publisher: Elsevier B.V.
Abstract: Common drugs intended for action in plasma (antibacterials, antiallergics, diuretics¿) often display both acidic and basic behavior, and some of these amphoteric compounds can appear as zwitterions. In such cases, accurate profiling of lipophilicity vs. pH, which plays a fundamental role in drug pharmacokinetics, might be complex. In the present work two common lipophilicity estimation methods based on the drug distribution between 1-octanol and aqueous buffer i.e. phase equilibration (shake-flask) and two-phase titration (potentiometry), were compared with a high-throughput lipophilicity index, the Chromatographic Hydrophobicity Index (CHI). The results were also compared with log Do/w pH-profiles calculated by different algorithms from ACD/Labs. Accurate and similar results were obtained for both octanol-water approaches but, due to the lower determination times and the absence of different ion-pairing buffers, potentiometry was shown to be the most convenient method. CHI vs. pH profiles provide rapid and efficient information, which is very convenient for lipophilicity screening purposes, but may differ slightly from shake-flask and potentiometric results.
Note: Versió postprint del document publicat a:
It is part of: Talanta, 2016, vol. 162, p. 293-299
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ISSN: 0039-9140
Appears in Collections:Articles publicats en revistes (Enginyeria Química i Química Analítica)

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