New frontiers in physical form discovery: High-pressure recrystallization of pharmaceuticals and other molecular compounds

NATO Science for Peace and Security Series B: Physics and Biophysics

Volumn , Issue , 2010, Pages 545-558

  Fabbiani, Francesca P A ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Crystallization; DAC; Pharmaceuticals; Physical form discovery

Indexed keywords

EID: 77954239145     PISSN: 18746500     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-90-481-9258-8_45     Document Type: Article

References (76)

1. Almarsson, Ö., and Zaworotko, M.J., 2004, Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem. Commun.: 1889-1896.
2. Bernstein, J. 2002, Polymorphism in Molecular Crystals, Clarendon Press, Oxford.
3. Boldyrev, V.V., 2004, Mechanochemical modification and synthesis of drugs, J. Mater. Sci. 39: 5117-5120, and references therein.
4. Boldyreva, E.V., 2003 High-pressure studies of the anisotropy of structural distortion of molecular crystals, J. Mol. Struct. 647: 159-179, and references therein.
5. Boldyreva, E.V., 2004, Molecules in strained environment, in: High-Pressure Crystallograph, edited by A. Katrusiak and P.F. McMillan, Kluwer, Dordrecht, pp. 495-512.
6. Boldyreva, E.V., 2007a, Crystalline amino acids - a link between chemistry, materials science and biology, In: Models, Mysteries, and Magic of Molecules, edited by J.C.A. Boeyens, J.F. Ogilvie, Springer Verlag, New York, pp. 169-194.
7. Boldyreva, E.V., 2007b, High-pressure polymorphs of molecular solids: when are they formed, and when are they not? Some examples of the role of kinetic control, Cryst. Growth Des. 7(9): 1662-1668, and reference therein.
8. Boldyreva, E.V., 2007c, High-pressure studies of crystalline amino acids and simple peptides/ Proceedings of the IV-th International Conference on High Pressures in Biosciences and Biotechnology, Presented by J-STAGE, Tsukuba, Japan, September, 25th-26th 2006, edited by F. Abe, A. Suzuki, Japan Science and Technology Agency: Saitama, Japan, 1(1): 28-46.
9. Boldyreva, E.V., 2008, High-pressure diffraction studies of molecular organic solids. A personal view, Acta Cryst. A 64: 218-231, and reference therein.
10. Boldyreva, E.V., 2009, Combined X-ray diffraction and Raman spectroscopy studies of phase transitions in crystalline amino acids at low temperatures and high pressures. Selected examples / Phase Transitions, 82(4): 303-321.
11. Boldyreva, E.V., Shakhtshneider, T.P., Vasilchenko, M.A., Ahsbahs, H., and Uchtmann H., 2000, Anisotropic crystal structure distortion of the monoclinic polymorph of acetaminophen at high hydrostatic pressure, Acta Cryst. B. 56: 299-309.
12. Boldyreva, E.V., Shakhtshneider, T.P., Ahsbahs, H., Sowa, H., and Uchtmann, H., 2002, Effect of high pressure on the polymorphs of paracetamol, J. Therm Anal. Calorim. 66: 437-452.
13. Boldyreva, E.V., Dmitriev, V.P., and Hancock, B.C., 2006, Effect of pressure up to 5.5 GPa on dry powder samples of chlorpropamide form-A, Int. J. Pharm. 327: 51-57.
14. Bridgman, P.W., 1931, The Physics of High Pressure, G. Bell & Sons, London.
15. Brittain, H.G., and Fiese, E.F., 1999, Effects of pharmaceutical processing on drug polymorphs and solvates, in: Polymorphism in Pharmaceutical Solids, edited by H.G. Brittain, Marcel Dekker, New York, pp. 331-361.
16. Byrn, S., Pfeiffer, R., Ganey, M., Hoiberg, C., Poochikian, G., 1995, Pharmaceutical solids: a strategic approach to regulatory considerations, Pharm. Res. 12: 945-954.
17. Day, G.M., Cooper, T.G., Cruz-Cabeza, A.J., Hejczyk, K.E., Ammon, H.L., Boerrigter, S.X.M., Tan, J.S., Della Valle, R.G., Venuti, E., Jose, J., Gadre, S.R., Desiraju, G.R., Thakur, T.S., van Eijck, B.P., Facelli, J.C., Bazterra, V.E., Ferraro, M.B., Hofmann, D.W.M., Neumann, M.A., Leusen, F.J.J., Kendrick, J., Price, S.L., Misquitta, A.J., Karamertzanis, P.G., Welch, G.W.A., Scheraga, H.A., Arnautova, Y.A., Schmidt, M.U., van de Streek, J., Wolf, A.K., and Schweizer, B., 2009, Significant progress in predicting the crystal structures of small organic molecules - a report on the fourth blind test, Acta Cryst. B 65: 107-125.
18. Dziubek, K.F., and Katrusiak, A., 2008, Polar symmetry in new high-pressure phases of chloroform and bromoform, J. Phys. Chem. B 112: 12001-12009.
19. Fabbiani, F.P.A., and Pulham, C.R., 2006, High-pressure studies of pharmaceutical compounds and energetic materials, Chem. Soc Rev. 35: 932-942.
20. Fabbiani, F.P.A., Allan, D.R., Dawson, A.D., David, W.I.F., McGregor, P.A., Oswald, I.D.H., Parsons, S., and Pulham, C.R., 2003, Pressure-induced formation of a solvate of paracetamol, Chem. Commun.: 3004-3005.
21. Fabbiani, F.P.A., Allan, D.R., David, W.I.F., Moggach, S.A., Parsons, S., and Pulham, C.R., 2004, High-pressure recrystallisation - a route to new polymorphs and solvates, CrystEngComm. 6: 504-511.
22. Fabbiani, F.P.A., Allan, D.R., Marshall, W.G., Parsons, S., Pulham, C.R., and Smith, R.I., 2005a, High-pressure recrystallisation - a route to new polymorphs and solvates of acetamide and parabanic acid, J. Cryst. Growth 275: 185-192.
23. Fabbiani, F.P.A., Allan, D.R., Parsons, S., and C.R. Pulham, 2005b, An exploration of the polymorphism of piracetam using high pressure, Cryst. Eng. Comm. 7(29): 179-186.
24. Fabbiani, F.P.A., Allan, D.R., Parsons, S., and Pulham, C.R., 2006, Exploration of the highpressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene, Acta Cryst. B 62: 826-842.
25. Fabbiani, F.P.A., Allan, D.R., David, W.I.F., Davidson, A.J., Lennie, A.R., Parsons, S., Pulham, C.R., and Warren, J.E., 2007, High-pressure studies of pharmaceuticals: an exploration of the behavior of piracetam. Cryst. Growth Des. 7(4): 1115-1124.
26. Fabbiani, F.P.A., Dittrich, B., Florence, A.J., Gelbrich, T., Hursthouse, M.B., Kuhs, W.F., Shankland, N., and Sowa, H., 2009, Crystal structures with a challenge: high-pressure crystallisation of ciprofloxacin sodium salts and their recovery to ambient pressure, Cryst. Eng. Comm. 11(7): 1396-1406.
27. Favre-Nicolin, V., and Černý, R., 2002, FOX, free objects for crystallography: a modular approach to ab initio structure determination from powder diffraction J. Appl. Cryst. 35: 734-743.
28. Florence, A.J., Johnston, A., Price, S.L., Nowell, H., Kennedy, A.R., and Shankland, N., 2006, An automated parallel crystallisation search for predicted crystal structures and packing motifs of carbamazepine, J. Pharm. Sci. 95: 1918.
29. Fourme, R., 1968, Appareillage pour études radiocristallographiques sous pression et à température variable, J. Appl. Cryst. 1: 23-30.
30. Gajda, R., Dziubek, K. F., and Katrusiak, A., 2006, Absence of halogen . . . halogen interactions in chlorotrimethylsilane polymorphs, Acta Cryst. B 62: 86-93.
31. Gardner, C.R., Walsh, C.T., and Almarsson, Ö., 2004, Drugs as materials: valuing physical form in drug discovery, Nat. Rev. Drug Discov. 3(11): 926-934.
32. Gavezzotti, A., 2007, Molecular Aggregation: Structure Analysis and Molecular Simulation of Crystals and Liquids, Oxford University Press, Oxford.
33. Gelbrich, T., and Hursthouse, M.B., 2005, A versatile procedure for the identification, description and quantification of structural similarity in molecular crystals, Cryst. Eng. Comm. 7: 324-336.
34. Girard, E., Dhaussy, A.-C., Couzinet, B., Chervin, J.-C., Mezouar, M., Kahn, R., Ascone, I., and Fourme, R., 2007, Toward fully fledged high-pressure macromolecular crystallography, J. Appl. Cryst. 40: 912-918, and references therein.
35. Goryainov, S.V., Boldyreva, E.V., and Kolesnik, E.N., 2006, Raman observation of a new (δ) polymorph of glycine? Chem. Phys. Lett. 419: 496-500.
36. Grant, D.J.W., 1999, Theory and origin of polymorphism, in: Polymorphism in Pharmaceutical Solids, edited by H. G. Brittain, Marcel Dekker, New York, pp. 1-33.
37. Hazen, R.M., and Downs, R.T., (Eds.), 2000, High-Temperature and High-Pressure Crystal Chemistry, The Mineralogical Society of America, Washington, D.C., 41.
38. Hemley, R.J., 2000, Effects of high pressure on molecules, Annu. Rev. Phys. Chem. 51:763-800.
39. Hemley, R.J., and Dera, P., 2000, Molecular crystals, in: High-Temperature and High-Pressure Crystal Chemistry, edited by R.M. Hazen and R.T. Downs, The Mineralogical Society of America, Washington, D.C., 41, pp. 355-420.
40. Hilfiker, R., (Ed.), 2006, Polymorphism in the Pharmaceutical Industry, Wiley-VCH: Weinheim.
41. Kadri, A., Lorber, B., Charron, C., Robert, M.-C., Capelle, B., Damak, M., Jenner, G., and Giegé, R., 2005, Crystal quality and differential crystal-growth behaviour of three proteins crystallized in gel at high hydrostatic pressure, Acta Cryst. D 61: 784-788.
42. Katrusiak, A., 1991, High-pressure X-ray diffraction studies on organic crystals, Cryst. Res. Technol. 26: 523-531, and references therein.
43. Katrusiak, A., 2008, High-pressure crystallography, Acta Cryst. A 64: 135-148.
44. Katrusiak, A., and Dauter, Z., 1996, Compressibility of lysozyme protein crystals by X-ray diffraction, Acta Cryst. D 52: 607-608.
45. Katrusiak, A., and McMillan, P., 2004, (Eds.) High-Pressure Crystallography, Kluwer, Dordrecht.
46. Khankari, R.K., and Grant, D.J.W., 1995 Pharmaceutical hydrates, Thermochim. Acta 248:61-79.
47. Lozano-Casal, P., Allan, D.R., and Parsons, S., 2005, Pressure-induced polymorphism in cyclopropyl-amine, Acta Cryst. B 61: 717-723.
48. Markvardsen, A.J., David, W.I.F., and Shankland, K., 2002, A maximum likelihood method for global optimization based structure solution from powder diffraction data, Acta Cryst. A 58: 316-326.
49. McGregor, P.A., Clark, S.J., Allan, D.R., and Parsons, S., 2006, Hexamer formation in tertiary butyl alcohol (2-methyl-2-propanol, C4H10O), Acta Cryst. B 62: 599-605.
50. McMillan, P.F., 2003, Chemistry of materials under extreme high-pressure-high-temperature conditions, Chem. Commun. 8: 919-923.
51. Meersman, F., Dobson, C.M., and Heremans, K., 2006, Protein unfolding, amyloid fibril formation and configurational energy landscapes under high pressure conditions, Chem. Soc. Rev. 35: 908-917.
52. Moggach, S.A., Parsons, S., and Wood, P.A., 2008, High pressure polymorphism in amino acids, Crystallogr. Rev. 14: 143-184, and references therein.
53. Moggach, S.A., Bennett, T.D. and Cheetham, A.K., 2009, The Effect of Pressure on ZIF-8: increasing pore size with pressure and the formation of a high-pressure phase at 1.47 GPa, Angew. Chem. Int. Ed. 48(38): 7087-7089.
54. Okumura, T., Ishida, M., Takayama, K., and Otsuka, M., 2006, Polymorphic transformation of indomethacin under high pressures, J. Pharm. Sci. 95: 689-700.
55. Olejniczak, A., and Katrusiak, A., 2008, Supramolecular reaction between pressure-frozen acetonitrile phases α and β, J. Phys. Chem. B 112: 7183-7190.
56. Olejniczak, A., Katrusiak, A., and Vij, A., 2009a, Halogenoxygen aggregation and disorder modes in pressure frozen XCF2CF2X:1,4-dioxane (X = Br, I) complexes, Cryst. Eng. Comm. 11(7): 1240-1244.
57. Olejniczak, A., Katrusiak, A., Metrangolo, P., and Resnati, G., 2009b, Molecular association in 2-bromo-2-chloro-1,1,1-trifluoroethane (Halothane), J. Fluor. Chem. 130: 248-253.
58. Oswald, I.D.H., and Pulham, C.R., 2008, Co-crystallisation at high pressure - an additional tool for the preparation and study of co-crystals, Cryst. Eng. Comm. 10: 1114-1116.
59. Oswald, I.D.H., Chataigner, I., Elphick, S., Fabbiani, F.P.A., Lennie, A.R., Maddaluno, J., Marshall, W. G., Pulham, C.R., Prior, T.J., and Smith, R.I., 2009, Putting pressure on elusive polymorphs and solvates, Cryst. Eng. Comm. 11: 359-366.
60. Palatinus, L., Steurer, W., and Chapuis, G., 2007, Extending the charge-flipping method towards structure solution from incomplete data sets, J. Appl. Cryst. 40: 456-462.
61. Podsiadło, M., and Katrusiak, A., 2008, Competing patterns of weak directional forces in pressure-frozen CH2ClI and CH2I2, J. Phys. Chem. B 112: 5355-5362.
62. Prescimone, A., Milios, C. J., Moggach, S. A., Warren, J. E., Lennie, A. R., Sanchez-Benitez, J., Kamenev, K., Bircher, R., Murrie, M., Parsons, S., and Brechin, E. K., 2008, [Mn6] under pressure: a combined crystallographic and magnetic study, Angew. Chem., Int. Ed. 47(15): 2828-2831.
63. Price, S.L., 2009, Computed crystal energy landscapes for understanding and predicting organic crystal structures and polymorphism, Acc. Chem. Res. 42(1): 117-126.
64. Pruzan, P., Chervin, J.C., Thiery, M.M., Itie, J.P., Besson, J.M., Forgerit, J.P., and Revault, M.J., 1990, Transformation of benzene to a polymer after static perssurization to 30 GPa, Chem. Phys. 92: 6910-6915.
65. Rossmann, M.G., 2001, Molecular replacement - historical background, Acta Cryst. D 57: 1360-1366.
66. Sawamura, S., Fujita, N., 2007, High-pressure solubility of fullerene C60 in toluene. Carbon 45(5): 965-970.
67. Shakhtshneider T.P., Boldyreva E.V., Vasilchenko M.A., Ahsbahs, H., Uchtmann, H., 1999, Anisotropy of structural strain in molecular organic crystals on hydrostatic compression, J. Struct. Chem. 40(6): 1140-1148.
68. Shakhtshneider T.P., Boldyreva E.V., Vasilchenko M.A., Ahsbhas, H., Uchtmann, H., 1998, A comparison of the anisotropy of hydrostatic compression of the crystalline structures of paracetamol and phenacetine, Doklady Phys. Chem. 363(6): 783-786.
69. Spackman, M.A., and Jayatilaka, D., 2009, Hirshfeld surface analysis, Cryst. Eng. Comm 11: 19-32.
70. Stahl, P.H., and Wermuth, C.G., (Eds.) 2002, Handbook of Pharmaceutical Salts: Properties, Selection and Use, Wiley-VCH, Chichester.
71. Stahly, G.P., 2007, Diversity in single- and multiple-component crystals. The search for and prevalence of polymorphs and cocrystals, Cryst. Growth Des. 7(6): 1007-1026.
72. Suzuki, Y., Sazaki, G., Miyashita, S., Sawada, T., Tamura, K., Komatsu, H., 2002, Protein crystallization under high pressure, Biochim. Biophys. Acta 1595: 345-356.
73. Tonkov, E.Y., and Ponyatovsky, E.G., 2005, Phase Transformations of Elements under Pressure, CRC Press, Boca Raton, FL.
74. Tozuka, Y., Kawada, D., Oguchi, T., Yamamoto, K., 2003, Supercritical carbon dioxide treatment as a method for polymorph preparation of deoxycholic acid, Int. J. Pharm. 263: 45-50.
75. Wood, P.A., Forgan, R.S., Lennie, A.R., Parsons, S., Pidcock, E., Tasker, P.A., and Warren, J. E., 2008, The effect of pressure and substituents on the size of pseudo-macrocyclic cavities in salicylaldoxime ligands, Cryst. Eng. Comm. 10: 239-251.
76. Yamashita, M., Inomata, S., Ishikawa, K., Kashiwagi, T., Matsuo, H., Sawamura, S., and Kato, M., 2007, A high-pressure polymorph of L-α-leucine, Acta Cryst. E 63: o2762-o2764.