2024
DOI: 10.1021/acs.jmedchem.4c00596
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Nonclassical Zwitterions as a Design Principle to Reduce Lipophilicity without Impacting Permeability

Henrik Möbitz,
Birger Dittrich,
Stephane Rodde
et al.

Abstract: The ionization of bioactive molecules impacts many ADME-relevant physicochemical properties, in particular, solubility, lipophilicity, and permeability. Ampholytes contain both acidic and basic groups and are distinguished as ordinary ampholytes and zwitterions. An influential review states that zwitterions only exist if the acidic pK a is significantly lower than the basic pK a. Through concordance of measured and calculated pK a and log P, we show that the zwitterionic behavior of several marketed drugs and … Show more

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