Table 1. Physicochemical Properties of Selected Model Compoundsa.
| compound | Mw (Da) | logP | Tm (°C) | ΔSf (J/mol·K) | TPSA | A/B/N/Am | pKab |
|---|---|---|---|---|---|---|---|
| acitretin | 326.5 | 5.6 | 221 | 115 | 47 | A | 4.2 |
| albendazole | 265.4 | 3.1 | 203 | 95 | 92 | Am | 3.7, 9.926 |
| bezafibrate | 361.9 | 3.8 | 185 | 110 | 76 | A | 3.643 |
| candesartan | 440.5 | 4.6 | 178 | nd | 119 | Am | 2.1, 3.3, 4.544 |
| candesartan cilexetil | 610.7 | 7.4 | 167 | 116 | 143 | Am | 3.0, 2.2 |
| carbamazepine | 236.3 | 2.7 | 173c | nd | 48 | N | na |
| cinnarizine | 368.6 | 5.5 | 119 | 103 | 6 | B | 7.526 |
| clofazimine | 473.4 | 6.9 | 222 | 74 | 42 | B | 9.045 |
| clotrimazole | 344.9 | 5.2 | 142 | 77 | 18 | B | 5.2 |
| danazol | 337.5 | 4.9 | 227 | 63 | 46 | N | na |
| diflunisal | 250.2 | 3.1 | 213 | 76 | 58 | A | 3.145 |
| dipyridamole | 504.7 | 2.5 | 166 | 72 | 145 | B | 6.226 |
| disulfiram | 296.6 | 4.6 | 67 | 84 | 121 | B | 2.5 |
| ethinylestradiol | 296.4 | 4.9 | 183 | 62 | 40 | A | 10.3 |
| felodipine | 384.3 | 3.6 | 143 | 73 | 65 | N | na |
| fenbendazole | 299.4 | 3.8 | 226 | 123 | 92 | B | 5.146 |
| fenofibrate | 360.9 | 5.1 | 79 | 85 | 53 | N | na |
| fenofibric acid | 318.8 | 4.1 | 184 | 99 | 64 | A | 3.5 |
| glibenclamide | 494.1 | 4.1 | 174 | 99 | 122 | A | 5.926 |
| griseofulvin | 352.8 | 2.2 | 217 | 87 | 71 | N | na |
| halofantrine | 500.5 | 8.2 | 77 | 89 | 23 | B | 9.2 |
| haloperidol | 375.9 | 3.9 | 151 | 133 | 41 | B | 8.626 |
| indomethacin | 357.8 | 4.2 | 160 | 80 | 69 | A | 3.926 |
| itraconazole | 705.7 | 6.5 | 166 | 128 | 105 | B | 3.945 |
| mefenamic acid | 241.3 | 4.0 | 230 | 74 | 49 | A | 4.445 |
| naproxen | 230.3 | 2.8 | 155 | 75 | 47 | A | 4.226 |
| niclosamide | 327.1 | 3.6 | 231 | 87 | 95 | A | 10.3, 8.1 |
| noscapine | 413.5 | 3.0 | 175 | 80 | 76 | B | 5.9 |
| perphenazine | 404.0 | 4.2 | 94 | 86 | 60 | B | 7.828 |
| praziquantel | 312.5 | 2.7 | 139 | 72 | 41 | N | na |
| progesterone | 314.5 | 3.6 | 128 | 63 | 34 | N | na |
| saquinavir | 670.9 | 3.9 | nd | nd | 167 | B | 7.447 |
| sulfasalazine | 398.4 | 2.0 | 255 | 99 | 146 | A | 10.9, 8.0, 2.448 |
| tolfenamic acid | 261.7 | 4.1 | 213 | 78 | 49 | A | 4.126 |
| toltrazuril | 425.4 | 6.1 | 192 | 89 | 111 | A | 8.2 |
a
Molecular weight (Mw), logP (displays AlogP), and TPSA (displays TPSA(Tot)) were calculated with DragonX 6.0.16 (Talete, Italy). Melting point (Tm) and entropy of fusion (ΔSf) were determined with differential scanning calorimetry (see Experimental Section). Abbreviations: acid (A); base (B); neutral in the pH range 2–12 (N); ampholyte (Am).
b
pKa data was collected from the literature or, if not available in the literature, predicted through ADMET Predictor v7.1 (Lancaster, CA).
c
Tm of carbamazepine corresponds to form III (see Results).