9 Pharmaceutical Multicomponent Crystals: Structure, Design …
181
3. Lynn, E.J., Walter, R.G., Harris, L.A., Dendy, R., James, M.J.: Nitrous oxide: it’s a gas.
Psychedelic Drugs 5, 1–7 (1972)
4. Vippagunta, S.R., Brittain, H.G., Grant, D.J.W.: Crystalline solids. Adv. Drug. Deliv. Rev. 48,
3–26 (2001)
5. Shan, N., Zawarotko, M.J.: The role of cocrystals in pharmaceutical science. Drug Discov.
Today 13, 440–446 (2008)
6. Byrn, S.R., Pfeiffer, R.R., Stephenson, G., Grant, D.J.W., Gleason, W.B.: Solid-state pharmaceutical chemistry. Chem. Mater. 6, 1148–1158 (1994)
7. Cheney, M.L., Weyna, D.R., Shan, N., Hanna, M., Wojtas, L., Zawarotko, M.J.: Supramolecular
architectures of meloxicam carboxylic acid cocrystals, a crystal engineering case study. Cryst.
Growth Des. 10, 4401–4413 (2010)
8. Sun, C.C., Hou, H.: improving mechanical properties of caffeine and methyl gallate crystals
by cocrystallization. Cryst. Growth Des. 8, 1575–1579 (2008)
9. Chen, S., Guzei, I.A., Yu, L.: New polymorphs of ROY and new record for coexisting
polymorphs of solved structures. J. Am. Chem. Soc. 127(27), 9881–9885 (2005)
10. Yu, L.: Polymorphism in molecular solids: an extraordinary system of red, orange, and yellow
crystals. Acc. Chem. Res. 43, 1257–1266 (2010)
11. Bryn, S., Pfeiffer, R., Ganey, M., Hoiberg, C., Poochikian, G.: Pharmaceutical solids: a strategic
approach to regulatory considerations. Pharm. Res. 12, 945–954 (1995)
12. Aitipamula, S., Banerjee, R., Bansal, A.K., Biradha, K., Cheney, M.L., Choudhury, A.R.,
Desiraju, G.R., et al.: Polymorphs, salts, and cocrystals: what’s in a name? Cryst. Growth Des.
12, 2147–2152 (2012)
13. Grothe, E., Meekes, H., Vlieg, E., ter Horst, J.H., de Gelder, R.: Solvates, salts, and cocrystals:
a proposal for a feasible classification system. Cryst. Growth Des. 16, 3237–3243 (2016)
14. Kavanagh, O.N., Croker, D.M., Walker, G.M., Zaworotko, M.J.: Pharmaceutical cocrystals:
from serendipity to design to application. Drug Discov. Today 24, 796–804 (2019)
15. Hancock, B.C., Zografi, B.: Characteristics and significance of the amorphous state in
pharmaceutical systems. J. Pharm. Sci. 86, 1–12 (1997)
16. Hancock, B.C., Parks, M.: What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17, 397–404 (2000)
17. Grohganz, H., Lobman, K., Priemel, P., Jensen, K.T., Graeser, K., Rades, T.: Amorphous drugs
and dosage forms. J. Drug. Del. Sci. Tech. 23, 403–408 (2013)
18. Sibik, J., Lobmann, K., Zeitler, T., Rades, J.A.: Predicting crystallization of amorphous drugs
with terahertz spectroscopy. Mol. Pharm. 12, 3062–3068 (2015)
19. Datta, S., Grant, D.J.W.: Crystal structures of drugs: advances in determination, prediction and
engineering. Nat. Rev. Drug Discov. 3, 42–57 (2004)
20. Bernstein, J.: Polymorphism in Molecular Crystals. Clarendon, Oxford (2002)
21. Morissette, S.L., Almarsson, O., Peterson, M.L., Remenar, J.F., Read, M.J., Lemmo, A.V., Ellis,
S., Cima, M.J., Gardner, C.R.: High-throughput crystallization: polymorphs, salts, co-crystals
and solvates of pharmaceutical solids. Adv. Drug. Deliv. Rev. 56, 275–300 (2004)
22. Hilfiker, R.: Polymorphism in the Pharmaceutical Industry. Wiley, Weinheim (2006)
23. Seddon, K.R.: Pseudopolymorph: a polemic. Cryst. Growth Des. 4, 1087–1087 (2004)
24. Bernstein, J.: …And another comment on pseudopolymorphism. Cryst. Growth Des. 5, 1661–
1662 (2005)
25. Putra, O.D., Pettersen, A., Lill, S.O.N., Umeda, D., Yonemochi, E., Nugraha, Y.P., Uekusa,
H.: Capturing a new hydrate polymorph of amodiaquine dihydrochloride dihydrate via
heterogeneous crystallization. Cryst. Eng. Commun. 2019(21), 2053–2057 (2019)
26. Healy, A.M., Worku, Z.A., Kumar, D., Madi, A.M.: Pharmaceutical solvates, hydrates and
amorphous forms: a special emphasis on cocrystals. Adv. Drug Deliv. Rev. 117, 25–46 (2017)
27. Vioglio, P.C., Chierotti, M.R., Gobetto, R.: Pharmaceutical aspects of salt and cocrystal forms
of APIs and characterization challenges. Adv. Drug Deliv. Rev. 117, 86–110 (2017)
28. Desiraju, G.R., Vittal, J.J., Ramanan, A.: Crystal Engineering: A Textbook. World Scientific,
Singapore (2011)
181
3. Lynn, E.J., Walter, R.G., Harris, L.A., Dendy, R., James, M.J.: Nitrous oxide: it’s a gas.
Psychedelic Drugs 5, 1–7 (1972)
4. Vippagunta, S.R., Brittain, H.G., Grant, D.J.W.: Crystalline solids. Adv. Drug. Deliv. Rev. 48,
3–26 (2001)
5. Shan, N., Zawarotko, M.J.: The role of cocrystals in pharmaceutical science. Drug Discov.
Today 13, 440–446 (2008)
6. Byrn, S.R., Pfeiffer, R.R., Stephenson, G., Grant, D.J.W., Gleason, W.B.: Solid-state pharmaceutical chemistry. Chem. Mater. 6, 1148–1158 (1994)
7. Cheney, M.L., Weyna, D.R., Shan, N., Hanna, M., Wojtas, L., Zawarotko, M.J.: Supramolecular
architectures of meloxicam carboxylic acid cocrystals, a crystal engineering case study. Cryst.
Growth Des. 10, 4401–4413 (2010)
8. Sun, C.C., Hou, H.: improving mechanical properties of caffeine and methyl gallate crystals
by cocrystallization. Cryst. Growth Des. 8, 1575–1579 (2008)
9. Chen, S., Guzei, I.A., Yu, L.: New polymorphs of ROY and new record for coexisting
polymorphs of solved structures. J. Am. Chem. Soc. 127(27), 9881–9885 (2005)
10. Yu, L.: Polymorphism in molecular solids: an extraordinary system of red, orange, and yellow
crystals. Acc. Chem. Res. 43, 1257–1266 (2010)
11. Bryn, S., Pfeiffer, R., Ganey, M., Hoiberg, C., Poochikian, G.: Pharmaceutical solids: a strategic
approach to regulatory considerations. Pharm. Res. 12, 945–954 (1995)
12. Aitipamula, S., Banerjee, R., Bansal, A.K., Biradha, K., Cheney, M.L., Choudhury, A.R.,
Desiraju, G.R., et al.: Polymorphs, salts, and cocrystals: what’s in a name? Cryst. Growth Des.
12, 2147–2152 (2012)
13. Grothe, E., Meekes, H., Vlieg, E., ter Horst, J.H., de Gelder, R.: Solvates, salts, and cocrystals:
a proposal for a feasible classification system. Cryst. Growth Des. 16, 3237–3243 (2016)
14. Kavanagh, O.N., Croker, D.M., Walker, G.M., Zaworotko, M.J.: Pharmaceutical cocrystals:
from serendipity to design to application. Drug Discov. Today 24, 796–804 (2019)
15. Hancock, B.C., Zografi, B.: Characteristics and significance of the amorphous state in
pharmaceutical systems. J. Pharm. Sci. 86, 1–12 (1997)
16. Hancock, B.C., Parks, M.: What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17, 397–404 (2000)
17. Grohganz, H., Lobman, K., Priemel, P., Jensen, K.T., Graeser, K., Rades, T.: Amorphous drugs
and dosage forms. J. Drug. Del. Sci. Tech. 23, 403–408 (2013)
18. Sibik, J., Lobmann, K., Zeitler, T., Rades, J.A.: Predicting crystallization of amorphous drugs
with terahertz spectroscopy. Mol. Pharm. 12, 3062–3068 (2015)
19. Datta, S., Grant, D.J.W.: Crystal structures of drugs: advances in determination, prediction and
engineering. Nat. Rev. Drug Discov. 3, 42–57 (2004)
20. Bernstein, J.: Polymorphism in Molecular Crystals. Clarendon, Oxford (2002)
21. Morissette, S.L., Almarsson, O., Peterson, M.L., Remenar, J.F., Read, M.J., Lemmo, A.V., Ellis,
S., Cima, M.J., Gardner, C.R.: High-throughput crystallization: polymorphs, salts, co-crystals
and solvates of pharmaceutical solids. Adv. Drug. Deliv. Rev. 56, 275–300 (2004)
22. Hilfiker, R.: Polymorphism in the Pharmaceutical Industry. Wiley, Weinheim (2006)
23. Seddon, K.R.: Pseudopolymorph: a polemic. Cryst. Growth Des. 4, 1087–1087 (2004)
24. Bernstein, J.: …And another comment on pseudopolymorphism. Cryst. Growth Des. 5, 1661–
1662 (2005)
25. Putra, O.D., Pettersen, A., Lill, S.O.N., Umeda, D., Yonemochi, E., Nugraha, Y.P., Uekusa,
H.: Capturing a new hydrate polymorph of amodiaquine dihydrochloride dihydrate via
heterogeneous crystallization. Cryst. Eng. Commun. 2019(21), 2053–2057 (2019)
26. Healy, A.M., Worku, Z.A., Kumar, D., Madi, A.M.: Pharmaceutical solvates, hydrates and
amorphous forms: a special emphasis on cocrystals. Adv. Drug Deliv. Rev. 117, 25–46 (2017)
27. Vioglio, P.C., Chierotti, M.R., Gobetto, R.: Pharmaceutical aspects of salt and cocrystal forms
of APIs and characterization challenges. Adv. Drug Deliv. Rev. 117, 86–110 (2017)
28. Desiraju, G.R., Vittal, J.J., Ramanan, A.: Crystal Engineering: A Textbook. World Scientific,
Singapore (2011)