Table 2.
Examples of the transferability of cocrystallization landscapes characterizing the potential for the cocrystallization of various dicarboxylic acids with a few representative phenylpiperazine drugs
| API | (0) | (1) | (2) | (3) | (4) | (5) | (6) | (7) | (8) |
|---|---|---|---|---|---|---|---|---|---|
| Isoniazid | FADGEY | FADGIC | FADGOI | FADGUO | FADHAV | SETRUG | SETROA | ||
| + | (2:1) | (1:2) | (1:1) | (1:2) | (1:1) | (2:1) | + | (2:1) | |
| −2.61 | −0.53 | −0.89 | −0.90 | −0.79 | −0.72 | −0.73 | −0.62 | −0.53 | |
| Praziquantel | TELCOE | TELDEV | TELDAR | TELDIZ | TELCAQ | 54] | |||
| (1:1) | (1:1) | (1:1) | (1:1) | (1:2) | (1:1) | + | + | + | |
| −3.31 | −0.90 | −1.30 | −1.51 | −1.42 | −1.40 | −1.55 | −1.44 | −1.29 | |
| Caffeine | GANXUP | GANYAW | EXUQUJ | CESKAN | [55] | ||||
| (1:2) | (1:2) | + | (1:1) | (1:1) | + | (1:1) | + | + | |
| −2.47 | −0.42 | −0.63 | −0.80 | −0.69 | −0.64 | −0.73 | −0.61 | −0.45 | |
| Pyrazine | GUDSUV | GUDTAC | VAXWAU | GUDTOQ | GUDVAE | ||||
| (1:1) | (1:1) | (1:1) | (1:1) | (1:1) | + | + | + | + | |
| −3.35 | −0.92 | −1.38 | −1.45 | −1.31 | −1.29 | −1.37 | −1.27 | −1.10 | |
| Carbamazepine | MOXWUS | MOXVUR | XOBCIB | MOXVOL | MOXVEB | ||||
| (1:1) | (1:1) | (0.5:1) | (1:1) | (0.5:1) | + | + | + | + | |
| −1.48 | −0.32 | −0.48 | −0.56 | −0.52 | −0.50 | −0.54 | −0.48 | −0.43 | |
| Pyrazinamide | SIHRAE | LATTOR | SIHQOR | [17] | [17] | ||||
| + | (1:1) | (0.5:1) | (1:1) | (1:1) | + | + | + | (1:1) | |
| −2.25 | −0.43 | −0.70 | −0.71 | −0.60 | −0.55 | −0.55 | −0.45 | −0.34 | |
| Phenazine | XAPMIK | ZUPLEB | WOQBOT | WOQBUZ | |||||
| (1:1) | (2:1) | (1:1) | (2:1) | + | + | + | + | + | |
| −3.24 | −0.71 | −1.19 | −1.43 | −1.34 | −1.28 | −1.44 | −1.30 | −1.17 | |
| Urotropine | MIPVEM | IJETOG | FITQII | EKECOM | |||||
| + | + | + | + | (1:1) | (1:1) | + | (1:1) | (1:1) | |
| −5.21 | −2.61 | −2.82 | −2.99 | −2.83 | −2.78 | −2.92 | −2.78 | −2.54 | |
| Theophylline | XEJWUF | XEJXAM | XEJXIU | ||||||
| (1:2) | (1:1) | + | (1:1) | + | + | + | + | + | |
| −1.99 | −0.30 | −0.47 | −0.58 | −0.48 | −0.42 | −0.48 | −0.37 | −0.26 | |
| Lamivudine | VISWAX | ||||||||
| + | – | + | – | – | (1:2) | – | – | – | |
| −1.24 | −0.17 | −0.21 | −0.17 | −0.14 | −0.05 | 0.01 | 0.09 | 0.09 |
The codes FADGEY, FADGIC, etc. relate to the record for this cocrystal in the Cambridge Structural Database (CSD). The data given for each cocrystal below the CSD code (if present; sometimes a relevant reference is cited instead, and sometimes there is no code nor reference for the cocrystal) are the stoichiometry of the cocrystals (if known; otherwise a “plus” symbol is shown) and the computed value of H mix (in kcal/mol). The numbers heading the columns are consistent with the DCA numbering scheme used in Fig. 1