The structure-property relations are examined for apremilast cocrystals and solvates in this work. A unique and large dataset of multicomponent crystal forms is presented including 7 cocrystals and 12 solvates. In total, 15 of the presented multicomponent forms and their crystal structures are published here for the first time. This dataset is unique owing to the extreme crystal packing similarity of all 19 crystal forms. This fact makes the evaluation of structure-property relations significantly easier and more precise since the differences in the crystal lattice arrangement are close to negligible. Properties of the guest molecules used here can be directly correlated with the macroscopic properties of the corresponding multicomponent forms. Interestingly, a considerable correlation was found between the intrinsic dissolution rate of the multicomponent forms and their solubility, as well as the solubility of their guest molecules in the dissolution medium. The latter is of particular interest as it can aid in the design of multicomponent forms with tuned properties.

Department of Chemical Engineering University of Chemistry and Technology Technická 3 Prague 6 16628 Czech Republic

Department of Solid State Chemistry University of Chemistry and Technology Technická 5 Prague 6 16628 Czech Republic

Institute of Physics of the Czech Academy of Sciences Na Slovance 2 Prague 8 18200 Czech Republic

Zentiva k s U kabelovny 130 Prague 10 10237 Czech Republic

Zobrazit více v PubMed

Aakeröy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474–480.

Afra, T. P., Razmi, T. M. & Dogra, S. (2019). Dermatol. Online J. 10, 1–12. PubMed PMC

Agharkar, S., Lindenbaum, S. & Higuchi, T. (1976). J. Pharm. Sci. 65, 747–749. PubMed

Aguiar, A. J., Krc, J. Jr, Kinkel, A. W. & Samyn, J. C. (1967). J. Pharm. Sci. 56, 847–853. PubMed

Aguiar, A. J. & Zelmer, J. E. (1969). J. Pharm. Sci. 58, 983–987. PubMed

Arlin, J.-B., Florence, A. J., Johnston, A., Kennedy, A. R., Miller, G. J. & Patterson, K. (2011). Cryst. Growth Des. 11, 1318–1327.

Banik, M., Gopi, S. P., Ganguly, S. & Desiraju, G. R. (2016). Cryst. Growth Des. 16, 5418–5428.

Bauer, J., Spanton, S., Henry, R., Quick, J., Dziki, W., Porter, W. & Morris, J. (2001). Pharm. Res. 18, 859–866. PubMed

Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487–1487.

Black, S. N., Collier, E. A., Davey, R. J. & Roberts, R. J. (2007). J. Pharm. Sci. 96, 1053–1068. PubMed

Blagden, N., de Matas, M., Gavan, P. T. & York, P. (2007). Adv. Drug Deliv. Rev. 59, 617–630. PubMed

Cadden, J., Klooster, W. T., Coles, S. J. & Aitipamula, S. (2019). Cryst. Growth Des. 19, 3923–3933.

Chen, H., Khemtong, C., Yang, X., Chang, X. & Gao, J. (2011). Drug Discovery Today, 16, 354–360. PubMed

Chiou, C. T., Freed, V. H., Schmedding, D. W. & Kohnert, R. L. (1977). Environ. Sci. Technol. 11, 475–478.

Collier, E. A., Davey, R. J., Black, S. N. & Roberts, R. J. (2006). Acta Cryst. B62, 498–505. PubMed

de Moraes, L. S., Edwards, D., Florence, A. J., Johnston, A., Johnston, B. F., Morrison, C. A. & Kennedy, A. R. (2017). Cryst. Growth Des. 17, 3277–3286.

Degen, T., Sadki, M., Bron, E., König, U. & Nénert, G. (2014). Powder Diffr. 29, S13–S18.

Dudek, M. K., Kostrzewa, M., Paluch, P. & Potrzebowski, M. J. (2018). Cryst. Growth Des. 18, 3959–3970.

Dudek, M. K., Wielgus, E., Paluch, P., Śniechowska, J., Kostrzewa, M., Day, G. M., Bujacz, G. D. & Potrzebowski, M. J. (2019). Acta Cryst. B75, 803–814. PubMed

Freire, M. G., Razzouk, A., Mokbel, I., Jose, J., Marrucho, I. M. & Coutinho, J. A. P. S. (2005). J. Chem. Eng. Data, 50, 237–242.

Gavhane, Y. N. & Yadav, A. V. (2012). Saudi Pharm. J. 20, 331–344. PubMed PMC

Good, D. J. & Rodríguez-Hornedo, N. (2009). Cryst. Growth Des. 9, 2252–2264.

Goud, N. R., Suresh, K. & Nangia, A. (2013). Cryst. Growth Des. 13, 1590–1601.

Gunnam, A. & Nangia, A. K. (2019). Cryst. Growth Des. 19, 5407–5417.

Isao, S., Masatake, A., Toshio, D. & Hideo, N. (1982). Bull. Chem. Soc. Jpn. 55, 1054–1062.

Jia, L., Zhang, Q., Wang, J.-R. & Mei, X. (2015). CrystEngComm, 17, 7500–7509.

Jirát, J., Ondo, D., Babor, M., Ridvan, L. & Šoóš, M. (2019). Int. J. Pharm. 570, 118639. PubMed

Jirát, J., Zvoníček, V., Babor, M., Ridvan, L., Skořepová, E., Dušek, M. & Šoóš, M. (2020). Cryst. Growth Des. 20, 5785–5795.

Lipinski, C. (2002). Am. Pharm. Rev. 5, 82–85.

Lipinski, C. A. (2000). J. Pharmacol. Toxicol. Methods, 44, 235–249. PubMed

Mannava, M. K. C., Dandela, R., Tothadi, S., Solomon, K. A. & Nangia, A. K. (2020). Cryst. Growth Des. 20, 3064–3076.

Martin, F. A., Pop, M. M., Borodi, G., Filip, X. & Kacso, I. (2013). Cryst. Growth Des. 13, 4295–4304.

Nian, J. (2016). Patent WO 2016141503 A1.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.

Parshad, H., Frydenvang, K., Liljefors, T., Sorensen, H. O. & Larsen, C. (2004). Int. J. Pharm. 269, 157–168. PubMed

Pinnamaneni, S., Das, N. G. & Das, S. K. (2002). Pharmazie, 57, 291–300. PubMed

Qiao, N., Li, M., Schlindwein, W., Malek, N., Davies, A. & Trappitt, G. (2011). Int. J. Pharm. 419, 1–11. PubMed

Rigaku Oxford Diffraction (2019). CrysAlisPro. Rigaku Oxford Diffraction, Yarnton, UK.

Rohlíček, J. & Hušák, M. (2007). J. Appl. Cryst. 40, 600–601.

Rohlíček, J., Skořepová, E., Babor, M. & Čejka, J. (2016). J. Appl. Cryst. 49, 2172–2183.

Sanphui, P., Bolla, G., Nangia, A. & Chernyshev, V. (2014). IUCrJ, 1, 136–150. PubMed PMC

Schultheiss, N. & Newman, A. (2009). Cryst. Growth Des. 9, 2950–2967. PubMed PMC

Stanton, M. K. & Bak, A. (2008). Cryst. Growth Des. 8, 3856–3862.

Stanton, M. K., Tufekcic, S., Morgan, C. & Bak, A. (2009). Cryst. Growth Des. 9, 1344–1352.

Stepanovs, D., Jure, M., Kuleshova, L. N., Hofmann, D. W. M. & Mishnev, A. (2015). Cryst. Growth Des. 15, 3652–3660.

Streng, W. H., Hsi, S. K., Helms, P. E. & Tan, H. G. H. (1984). J. Pharm. Sci. 73, 1679–1684. PubMed

Thakuria, R. & Nangia, A. (2013). Cryst. Growth Des. 13, 3672–3680.

Thayer, A. M. (2010). Chem. Eng. News Arch. 88, 13–18.

Valvanix, S. C., Yalkowsky, S. H. & Roseman, T. J. (1981). J. Pharm. Sci. 70, 502–507. PubMed

Van Arnum, S. D. (2000). Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley.

Wang, F. Y., Zhang, Q., Zhang, Z. Y., Gong, X. Y., Wang, J. R. & Mei, X. F. S. (2018). CrystEngComm, 20, 5945–5948.

Wu, Y. D., Zhang, X. L., Liu, X. H., Xu, J., Zhang, M., Shen, K., Zhang, S. H., He, Y. M., Ma, Y. & Zhang, A. H. (2017). Acta Cryst. C73, 305–313. PubMed

Yalkowsky, R. M. & Dannenfleser, S. H. (1992). Aquasol Database of Aqueous Solubility, version 5. Tucson, AZ: University of Arizona.

Yalkowsky, S. H. & He, Y. (2003). Handbook of Aqueous Solubility Data. Boca Raton, FL: CRC Press.

Yalkowsky, S. H., He, Y. & Jain, P. (2010). Handbook of Aqueous Solubility Data, 2nd ed. Boca Raton, FL: CRC Press.

Zerilli, T. & Ocheretyaner, E. (2015). Pharmacol. Ther. 40, 495–500. PubMed PMC

Zvoníček, V., Skořepová, E., Dušek, M., Žvátora, P. & Šoóš, M. (2018). Cryst. Growth Des. 18, 1315–1326.

Apremilast Cocrystals with Phenolic Coformers