Hostname: page-component-586b7cd67f-r5fsc Total loading time: 0 Render date: 2024-11-22T21:41:41.315Z Has data issue: false hasContentIssue false

Pharmaceutical Cocrystals: An Emerging Approach to Physical Property Enhancement

Published online by Cambridge University Press:  31 January 2011

Get access

Abstract

Pharmaceutical cocrystals are crystalline molecular complexes containing therapeutic molecules. They represent an emerging class of pharmaceutical materials offering the prospect of optimized physical properties. This article highlights important opportunities and challenges associated with the design and synthesis of pharmaceutical cocrystals. Cocrystallization is first placed into context with the more established approaches to physical property optimization of polymorph, hydrate, and salt selection. A directed, intermolecular-interaction-based approach to cocrystal design is described. The enhancement of specific physical properties, such as dissolution rate and physical stability, is illustrated by summarizing several recent reports. Synthetic approaches to cocrystallization are considered; in particular, the selectivity and screening-related opportunities afforded by solid-state grinding and solvent-drop grinding methods are discussed. Finally, an outlook on future developments summarizes the growth potential in this field, especially with regard to targeted, informatics-driven cocrystal screening approaches.

Type
Research Article
Copyright
Copyright © Materials Research Society 2006

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1. Datta, S. and Grant, D.J.W.Nat. Rev. Drug Disc. 3 (2004) p. 42.CrossRefGoogle Scholar
2. McCrone, W.C. in Physics and Chemistry of the Organic Solid State, Vol. II, edited by Fox, D., Labes, M.M. and Weissberger, A. (Interscience, New York, 1965).Google Scholar
3. Rodríguez-Spong, B., Price, C.P.Jayasankar, A.Matzger, A.J. and Rodríguez-Hornedo, N., Adv. Drug Deliv. Rev. 56 (2004) p. 241.CrossRefGoogle Scholar
4. Bernstein, J.Polymorphism in Molecular Crystals (Oxford University Press, Oxford, 2002).Google Scholar
5. Morissette, S.L.Almarsson, Ö., Peterson, M.L.Remenar, J.F.Read, M.J.Lemmo, A.V.Ellis, S.Cima, M.J. and Gardner, C.R.Adv. Drug Deliv. Rev. 56 (2004) p. 275.CrossRefGoogle Scholar
6. Motherwell, W.D.S.Ammon, H.L.Dunitz, J.D.Dzyabchenko, A.Erk, P.Gavezzotti, A.Hofmann, D.W.M.Leusen, F.J.J.Lommerse, J.P.M.Mooij, W.T.M.Price, S.L.Scheraga, H.Schweizer, B.Schmidt, M.U.Eijck, B.P.V.Verwer, P. and Williams, D.E.Acta Crystallogr. B58 (2002) p. 647.CrossRefGoogle Scholar
7. Khankari, R.K. and Grant, D.J.W.Thermochim. Acta 248 (1995) p. 61.CrossRefGoogle Scholar
8. Byrn, S.R.Pfeiffer, R.R. and Stowell, J.G.Solid-State Chemistry of Drugs, 2nd Ed. (SSCI, West Lafayette, IN, 1999).Google Scholar
9. Vippagunta, S.R.Brittain, H.G. and Grant, D.J.W.Adv. Drug Deliv. Rev. 48 (2001) p.3.CrossRefGoogle Scholar
10. Gillon, A.L.Feeder, N.Davey, R.J. and Storey, R.A.Cryst. Growth Des. 3 (2003) p.663.CrossRefGoogle Scholar
11. Gould, P.L.Int. J.Pharm. 33 (1986) p.201.CrossRefGoogle Scholar
12. Bighley, L.D.Berge, S.M. and Monkhouse, D.C. in Encyclopedia of Pharmaceutical Technology, Vol. 13, edited by Swarbrick, J. and Boylan, J.C. (Marcel Dekker, New York, 1996).Google Scholar
13. Bastin, R.J.Bowker, M.J. and Slater, B.J.Org. Process Res. Dev. 4 (2000) p.427.CrossRefGoogle Scholar
14. Stahl, P.H. and Wermuth, C.G.Handbook of Pharmaceutical Salts: Properties, Selection and Use (Verlag Helvetica Chimica Acta, Zurich, 2002).Google Scholar
15. Stahl, P.H. and Wermuth, C.G. Eds., Monographs on Acids and Bases, in Handbook of Pharmaceutical Salts: Properties, Selection and Use (Verlag Helvetica Chimica Acta, Zurich, 2002).Google Scholar
16. Etter, M.C.J. Phys. Chem. 95 (1991) p. 4601.CrossRefGoogle Scholar
17. Etter, M.C.Acc. Chem. Res. 23 (1990) p. 120.CrossRefGoogle Scholar
18. Allen, F. H., Acta Crystallogr. B58 (2002) p.380.CrossRefGoogle Scholar
19. Almarsson, Ö. and Zaworotko, M.J.Chem. Commun. (2004) p.1889.CrossRefGoogle Scholar
20. Oswald, I.D.H.Allan, D.R.McGregor, P.A.Motherwell, W.D.S.Parsons, S. and Pul-ham, C.R., Acta Crystallogr. B58 (2002) p.1057.CrossRefGoogle Scholar
21. Walsh, R.D. Bailey, Bradner, M.W.Fleisch-man, S., Morales, L.A.Moulton, B.Rodriguez-Hornedo, N., and Zaworotko, M.J.Chem. Commun. (2003) p.186.CrossRefGoogle Scholar
22. Fleischman, S.G.Kuduva, S.S.McMa-hon, J.A., Moulton, B.Walsh, R.D.B.Rodriguez-Hornedo, N., and Zaworotko, M.J.Cryst. Growth Des. 3 (2003) p.909.CrossRefGoogle Scholar
23. Remenar, J.F.Morissette, S.L.Peterson, M.L.Moulton, B.MacPhee, J.M.Guzmán, H.R., and Almarsson, Ö., J. Am. Chem. Soc. 125 (2003) p.8456.CrossRefGoogle Scholar
24. Childs, S.L.Chyall, L.J.Dunlap, J.T.Smolenskaya, V.N.Stahly, B.C. and Stahly, G.P.J.Am. Chem. Soc. 126 (2004) p.13335.CrossRefGoogle Scholar
25. Trask, A.V.Motherwell, W.D.S. and Jones, W.Cryst. Growth Des. 5 (2005) p.1013.CrossRefGoogle Scholar
26. Caira, M.R.Nassimbeni, L.R. and Wildervanck, A.F.J.Chem. Soc., Perkin Trans. 2 (1995) p.2213.CrossRefGoogle Scholar
27. Trask, A.V. and Jones, W. in Topics in Current Chemistry, Vol. 254, edited by Toda, F. (Springer, New York, 2005).Google Scholar
28. Chemburkar, S.R.Bauer, J.Deming, K.Spiwek, H.Patel, K.Morris, J., Henry, R.Span-ton, S., Dziki, W.Porter, W.Quick, J.Bauer, P.Donaubauer, J.Narayanan, B.A.Soldani, M.Riley, D. and McFarland, K.Org. Process Res. Dev. 4 (2000) p. 413.CrossRefGoogle Scholar
29. Trask, A.V.Streek, J. van de, Mother-well, W.D.S., and Jones, W.Cryst. Growth Des. 5 (2005) p. 2233.CrossRefGoogle Scholar
30. Shan, N.Toda, F. and Jones, W.Chem. Com-mun. (2002) p. 2372.CrossRefGoogle Scholar
31. Trask, A.V.Motherwell, W.D.S. and Jones, W.Chem. Commun. (2004) p. 890.CrossRefGoogle Scholar
32. Trask, A.V.Shan, N.Motherwell, W.D.S.Jones, W.Feng, S.Tan, R.B.H. and Carpenter, K.J.Chem. Commun. (2005) p.880.Google Scholar
33. Trask, A.V.Haynes, D.A.Motherwell, W.D.S. and Jones, W.Chem. Commun. (2006) p.51.CrossRefGoogle Scholar