Rabel SR, Patel M, Sun S and Maurin MB Electronic and Resonance Effects on the Ionization of Structural Analogues of Efavirenz AAPS PharmSci 2001;
3
(4)
article 28
(https://www.pharmsci.org/scientificjournals/pharmsci/journal/01_28.html).
Figures and Tables
Figure 1.Chemical structure of efavirenz and 4 efavirenz analogues.
Figure 2.pH-Solubility profile of Compound I. The data points (squares) represent experimentally determined values and the theoretical line (dotted line) represents the theoretical solubility profile generated using an ionization constant of 2.43 x 10-10 and an intrinsic solubility of 2.8 µg/mL.
Figure 3.pH-Solubility profile of Compound II. The data points (squares) represent experimentally determined values, and the theoretical line (dotted line) represents the theoretical solubility profile generated using an ionization constant of 4.34 x 10-11 and an intrinsic solubility of 1.6 µg/mL.
Figure 4.pH-Solubility profile of Compound III. The data points (squares) represent experimentally determined values, and the theoretical line (dotted line) represents the theoretical solubility profile generated using an ionization constant of 3.16 x 10-12 and an intrinsic solubility of 1.3 µg/mL.
Figure 5.pH-Solubility profile of Compound IV. The data points (squares) represent experimentally determined values, and the theoretical line (dotted line) represents the theoretical solubility profile generated using an ionization constant of 6.71 x 10-14 and an intrinsic solubility of 4400 µg/mL.
Table 1.
Summary of the Linear Regression and Ionization Constants from Equation 1
Table 2.
Electronegativities Associated with Atoms and Substituents on Efavirenz and Analogues of Efavirenz*
Figure 6.Correlation between the total electronegativity of substituents associated with each compound as a function of pKa .
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