A solubility comparison of neutral and zwitterionic polymorphs

Crystal Growth and Design

Volumn 14, Issue 4, 2014, Pages 1865-1881

  Kumar, S Sudalai ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DIFFERENTIAL SCANNING CALORIMETRY; DISSOLUTION; FUNCTIONAL GROUPS; HYDROGEN BONDS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE ANALYSIS; X RAY DIFFRACTION;

5-AMINOSALICYLIC ACIDS; ATTRACTIVE INTERACTIONS; CRYSTALLINE POLYMORPHS; FOURIER TRANSFORM INFRA REDS; POWDER X RAY DIFFRACTION; POWDER X-RAY DIFFRACTION (PXRD); SOLUBILITY ENHANCEMENT; X RAY CRYSTAL STRUCTURES;

SOLUBILITY;

EID: 84897491466     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg5000205     Document Type: Article

References (138)

1. López-Mejías, V.; Kampf, J.; Matzger, A. J. Am. Chem. Soc. 2012, 134, 9872
2. Haleblian, J.; McCrone, W. J. Pharm. Sci. 2006, 58, 911
3. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid-State Chemistry of Drugs, 2 nd ed.; SSCI Inc.: West Lafayette, 1999.
4. Dunitz, J.; Gavezzotti, A. J. Phys. Chem. B 2012, 116, 6740
5. Allen, K.; Davey, R. J.; Ferrari, E.; Towler, C.; Tiddy, G. J.T.; Jones, M.; Pritchard, R. G. Cryst. Growth Des. 2002, 2, 523
6. Kitamura, M. CrystEngComm 2009, 11, 949
7. Allen, F. H. Acta. Crystallogr., Sect. B 2002, B58, 380
8. Grant, D. J. W. Polymorphism in Pharmaceutical Solids; Brittain, H. G., Ed.; Marcel Dekker Inc.: New York, 1999; pp 1-32.
9. Mullin, J. W. Crystallization, 4 th ed.; Butterworth-Heinemann: Oxford, U.K., 2001.
10. McCrone, W. C. Polymorphism in Physics and Chemistry of the Organic Solid-State; Fox, D.; Labes, M. M.; Weissberger, A., Eds.; Wiley-Interscience: New York, 1965; Vol. 2, p 725.
11. Braga, D.; Grepioni, F. Making Crystals by Design; John-Wiley: New York, 2007; p 348.
12. Maher, A.; Rasmuson, Å. C.; Croker, D. M.; Hodnett, B. K. J. Chem. Eng. Data 2012, 57, 3525
13. Bartolomei, M.; Bertocchi, P.; Ramusino, M. C.; Santucci, N.; Valvo, L. J. Pharm. Biomed. Anal. 1999, 21, 299
14. Avdeef, A. Solubility, in Absorption and Drug Development: Solubility, Permeability, and Charge State, 2 nd ed.; John-Wiley: New York, 2012; p 251.
15. Lipinski, C.; Lombardo, F.; Dominy, B.; Feeney, P. Adv. Drug Delivery Rev. 2001, 46, 3
16. Lipinski, C. J. Pharmacol. Toxicol. Methods 2000, 44, 235
17. Urakami, K.; Shono, Y.; Higashi, A.; Umemoto, K.; Godo, M. Bull. Chem. Soc. Jpn. 2002, 75, 1241
18. Abramov, Y. A.; Pencheva, K. Thermodynamics and Relative Solubility Prediction of Polymorphic Systems, In Chemical Engineering in the Pharmaceutical Industry: R&D to Manufacturing; am Ende, D. J., Ed.; John-Wiley: New York, 2010; p 477.
19. Bauer, J.; Spanton, S.; Henry, R.; Quick, J.; Dziki, W.; Porter, W.; Morris, J. Pharm. Res. 2001, 18, 859
20. Sanphui, P.; Sarma, B.; Nangia, A. J. Pharm. Sci. 2011, 100, 2287
21. Cherukuvada, S.; Thakuria, R.; Nangia, A. Cryst. Growth Des. 2010, 10, 3931
22. Johnson, S. R.; Chen, X.-Q.; Murphy, D.; Gudmundsson, O. Mol. Pharmaceutics 2007, 4, 513
23. Lalit, R.; Sanphui, P.; Desiraju, G. R. Cryst. Growth. Des. 2010, 13, 3681
24. Babu, N. J.; Nangia, A. Cryst. Growth Des. 2011, 11, 2662
25. Serajuddin, A. Adv. Drug Delivery Rev. 2007, 59, 603
26. Llinàs, A.; Glen, R. C; Goodman, J. M. J. Chem. Inf. Model. 2008, 48, 1289
27. Alsenz, J.; Kansy, M. Adv. Drug Delivery Rev. 2007, 59, 546
28. Giron, D. Thermochim. Acta 1995, 248, 1
29. Bordallo, H.; Boldyreva, E.; Buchsteiner, A.; Koza, M.; Landsgesell, S. J. Phys. Chem. B 2008, 112, 8748
30. Hamilton, B. D.; Hillmyer, M. A.; Ward, M. D. Cryst. Growth Des. 2008, 8, 3368
31. Huang, J.; Yu, L. J. Am. Chem. Soc. 2006, 128, 1873
32. Moggach, S. A.; Parsons, S.; Wood, P. A. Cryst. Rev. 2008, 14, 143
33. Jamróz, M.; Rode, J.; Ostrowski, S.; Lipiński, P.; Dobrowolski, J. J. Chem. Inf. Model. 2012, 52, 1462
34. Luker, T.; Bonnert, R.; Paine, S.; Schmidt, J.; Sargent, C.; Cook, A.; Cook, A.; Gardiner, P.; Hill, S.; Weyman-Jones, C. J. Med. Chem. 2011, 54, 1779
35. Flaig, R.; Koritsanszky, T.; Dittrich, B.; Wagner, A.; Luger, P. J. Am. Chem. Soc. 2002, 124, 3407
36. Nath, N. K.; Kumar, S. S.; Nangia, A. Cryst. Growth Des. 2011, 11, 4594
37. Williams, P. A.; Hughes, C. E.; Lim, G. K.; Kariuki, B. M.; Harris, K. D. M Cryst. Growth Des. 2012, 12, 3104
38. Orola, L.; Veidis, M.; Sarcevica, I.; Actins, A.; Belyakov, S.; Platonenko, A. Int. J. Pharm. 2012, 432, 50
39. Trask, A.; Shan, N.; Motherwell, W.; Jones, W.; Feng, S.; Tan, R.; Carpenter, K. Chem. Commun. 2005, 880
40. Takasuka, M.; Nakai, H.; Shiro, M. J. Chem. Soc., Perkin Trans. 2 1982, 1061
41. Long, S.; Parkin, S.; Siegler, M. A.; Cammers, A.; Li, T. Cryst. Growth Des. 2008, 8, 4006
42. Long, S.; Li, T. Cryst. Growth Des. 2009, 9, 4993
43. Mahapatra, S.; Venugopala, K. N.; Row, T. N. G. Cryst. Growth Des. 2010, 10, 1866
44. Fabbiani, F. P. A.; Dittrich, B.; Florence, A. J.; Gelbrich, T.; Hursthouse, M. B.; Kuhs, W. F.; Shankland, N.; Sowa, H. CrystEngComm 2009, 11, 1396
45. Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074
46. Ojala, W. H.; Etter, M. C. J. Am. Chem. Soc. 1992, 114, 10288
47. Carter, P. W.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 769
48. Brown, C. J.; Ehrenberg, M. Acta Crystallogr., Sect. C 1985, C41, 441
49. Takazawa, H.; Ohba, S.; Saito, Y. Acta Crystallogr., Sect. C 1986, C42, 1880
50. Lu, T. H.; Chattopadhyay, P.; Liao, F. L.; Lo, J. M. Anal. Sci. 2001, 17, 905
51. Bag, P.; Reddy, C. M. Cryst. Growth Des. 2012, 12, 2740
52. Voogd, J.; Verzijl, B. H. M.; Duisenberg, A. J. M. Acta Crystallogr., Sect. B 1980, 36, 2805
53. Svärd, M.; Nordström, F. L.; Jasnobulka, T.; Rasmuson, Å. C. Cryst. Growth Des. 2010, 10, 195
54. López-Mejías, V.; Kampf, J. W.; Matzger, A. J. J. Am. Chem. Soc. 2009, 131, 4554
55. Lee, E. H.; Byrn, S. R.; Carvajal, M. T. Pharm. Res. 2006, 23, 2375
56. Tam, K.; Avdeef, A.; Tsinman, O.; Sun, N. J. Med. Chem. 2010, 53, 392
57. Towler, C.; Davey, R.; Lancaster, R.; Price, C. J. Am. Chem. Soc. 2004, 126, 13347
58. Torbeev, V. Y.; Shavit, E.; Weissbuch, I.; Leiserowitz, L.; Lahav, M. Cryst. Growth Des. 2005, 5, 2190
59. Srinivasan, K.; Devi, K. R.; Azhagan, S. A. Cryst. Res. Technol. 2011, 46, 159
60. Varma, M.; Gardner, I.; Steyn, S.; Nkansah, P.; Rotter, C.; Whitney-Pickett, C.; Zhang, H.; Di, L.; Cram, M.; Fenner, K.; El-Kattan, A. Mol. Pharm. 2012, 9, 1199
61. Bouchard, G.; Pagliara, A.; Carrupt, P.-A.; Testa, B.; Gobry, V.; Girault, H. Pharm. Res. 2002, 19, 1150
62. Sznitowska, M.; Janicki, S.; Gos, T. Int. J. Pharm. 1996, 137, 125
63. Avdeef, A. Curr. Top. Med. Chem. 2001, 1, 277
64. Pagliara, A.; Carrupt, P.-A.; Caron, G.; Gaillard, P.; Testa, B. Chem. Rev. 1997, 97, 3385
65. Mazák, K.; Noszál, B. J. Med. Chem. 2012, 55, 6942
66. Mazák, K.; Tóth, G.; Kökösi, J.; Noszál, B. Eur. J. Pharm. Sci. 2012, 47, 921
67. Tóth, G.; Mazák, K.; Hosztafi, S.; Kökösi, J.; Noszál, B. J. Pharm. Biomed. Anal. 2013, 76, 112
68. Okolotowicz, K. J.; Dwyer, M.; Smith, E.; Cashman, J. R. J. Biochem. Mol. Toxicol. 2013, 28, 23
69. Surov, A. O.; Terekhova, I. V.; Bauer-Brandl, A.; Perlovich, G. L. Cryst. Growth Des. 2009, 9, 3265
70. Moser, P.; Sallmann, A.; Wiesenberg, I. J. Med. Chem. 1990, 33, 2358
71. Perlovich, G. L.; Surov, A. O.; Hansen, L. K.; Brandl, A. B. J. Pharm. Sci. 2007, 96, 1031
72. Hee, E.; Lee, E. H.; Boerrigter, S. X. M.; Byrn, S. R. Cryst. Growth Des. 2010, 10, 518
73. Surov, A. O.; Szterner, P.; Zielenkiewicz, W.; Perlovich, G. L. J. Pharm. Biomed. Anal. 2009, 50, 831
74. Bertinotti, F.; Giacomello, C. Acta Crystallogr. 1954, 7, 808
75. Kornblum, S.; Sciarrone, B. J. Pharm. Sci. 1964, 53, 935
76. Apelblat, A.; Manzurola, E. J. Chem. Thermodyn. 1999, 31, 869
77. André, V.; Braga, D.; Grepioni, F.; Duarte, M. T. Cryst. Growth Des. 2009, 9, 5108
78. Montis, R.; Hursthouse, M. B. CrystEngComm 2012, 14, 5242
79. Banić-Tomišić, Z.; Kojić-Prodić, B.; Širola J. Mol. Struct. 1997, 416, 209
80. Forbes, R. T.; York, P.; Davidson, J. R. Int. J. Pharm. 1995, 126, 199
81. French, D. L.; Mauger, J. W. Pharm. Res. 1993, 10, 1285
82. Lichtenstein, G. Gastroenterol. Hepatol. 2009, 5, 65
83. Bernstein, J.; Davey, R. J.; Henck, J. O. Angew. Chem., Int. 1999, 38, 3441
84. Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Row, T. N. G. Cryst. Growth Des. 2004, 4, 1105
85. Long, S.; Siegler, M. A.; Mattei, A.; Li, T. Cryst. Growth Des. 2011, 11, 414
86. Long, S.; Parkin, S.; Siegler, M.; Brock, C. P.; Cammers, A.; Li, T. Cryst. Growth Des. 2008, 8, 3137
87. Cambridge Structural Database, ver. 5.34, ConQuest 1.15, November 2012 release, May 2013 update, Cambridge Crystallographic Data Center, www.ccdc.cam.ac.uk.
88. Desiraju, G. R. Chem. Commun. 1997, 1475
89. Etter, M. C. Acc. Chem. Res. 1990, 23, 120
90. Desiraju, G. R.; Vittal, J. J.; Ramanan, A. Crystal Engineering: A Textbook; World Scientific: Singapore, 2011; p 25.
91. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr. Sect. B 2004, B60, 627
92. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11, 19
93. Kumar, S. S.; Nangia, A. CrystEngComm 2013, 15, 6498
94. Minkov, V. S.; Tumanov, N. A.; Cabrerabc, R. Q.; Boldyreva, E. V. CrystEngComm 2010, 12, 2551
95. Nangia, A. Acc. Chem. Res. 2008, 41, 595
96. Nangia, A. Models, Mysteries and Magic of Molecules; Boeyens, J. C. A.; Ogilvie, J. F., Eds.; Springer: New York, 2008; p 63.
97. Kumar, S. S.; Rana, S.; Nangia, A. Chem. Asian J. 2013, 8, 1551
98. Cruz-Cabeza, A. J. CrystEngComm 2012, 14, 6362
99. Minkov, V. S.; Goryainov, S. V.; Boldyreva, E. V.; Görbitz, C. H. J. Raman Spectrosc. 2010, 41, 1748
100. Lee, A. Y.; Lee, I. S.; Myerson, A. S. Chem. Eng. Technol. 2006, 29, 281
101. Ramachandran, E.; Baskaran, K.; Natarajan, S. Cryst. Res. Technol. 2007, 42, 73
102. Sabino, A. S.; Sousa, G. P. D.; Luz-Lima, C.; Freire, P. T. C.; Melo, F. E. A.; Filho, J. Solid State Commun. 2009, 149, 1553
103. Sheth, A. R.; Lubach, J. W.; Munson, E. J.; Muller, F. X.; Grant, D. J. W. J. Am. Chem. Soc. 2005, 127, 6641
104. Chierotti, M. R.; Ferrero, L.; Garino, N.; Gobetto, R.; Pellegrino, L.; Braga, D.; Grepioni, F.; Maini, L. Chem. - Eur. J. 2010, 16, 4347
105. Brittain, H. G.; Morris, K.; Bugay, D.; Thakur, A.; Serajuddin, A. J. Pharm. Biomed. Anal. 1993, 11, 1063
106. Sen, S.; Yu, P.; Risbud, S.; Dick, R.; Deamer, D. J. Phys. Chem. B 2006, 110, 18058
107. Strohmeier, M.; Stueber, D.; Grant, D. M. J. Phys. Chem. A 2003, 107, 7629
108. Schmidt, H. L.; Sperling, L. J; Gao, Y. G.; Wylie, B. J.; Boettcher, J. M.; Wilson, S. R.; Rienstra, C. M. J. Phys. Chem. B 2007, 111, 14362
109. Geppi, D.; Mollica, G.; Borsacchi, S.; Veracini, C. Appl. Spectr. Rev 2008, 43, 202
110. Minkov, V. S.; Chesalov, Y. A.; Boldyreva, E. V. J. Struct. Chem. 2008, 49, 1061
111. Ebert, A. A., Jr.; Gottlieb, H. B. J. Am. Chem. Soc. 1952, 74, 2806
112. Colthup, N.; Daly, L. H.; Wiberley, S. E. Introduction to Infrared and Raman Spectroscopy, 3 rd ed.; Academic Press: Boston, 1990.
113. Wu, H.; Reeves-McLaren, N.; Jones, S.; Ristic, R. I. Cryst. Growth Des. 2010, 10, 988
114. Vippagunta, S.; Brittain, H.; Grant, D. Adv. Drug. Delivery Rev. 2001, 48, 3
115. Boldyreva, E.; Drebushchak, V.; Paukov, I.; Kovalevskaya, Y.; Drebushchak, T. J. Therm. Anal. Calorim. 2004, 77, 607
116. Kolesov, B.; Minkov, V.; Boldyreva, E.; Drebushchak, T. J. Phys. Chem. B 2008, 112, 12827
117. Zeitler, J.; Newnham, D.; Taday, P.; Threlfall, T.; Lancaster, R.; Berg, R.; Strachan, C.; Pepper, M.; Gordon, K.; Rades, T. J. Pharm. Sci. 2006, 95, 2486
118. Pranzo, M.; Cruickshank, D.; Coruzzi, M.; Caira, M.; Bettini, R. J. Pharm., Sci. 2010, 99, 3731
119. Yang, X.; Wang, X.; Ching, C. J. Chem. Eng. Data 2008, 53, 1133
120. Lyn, L.; Sze, H.; Rajendran, A.; Adinarayana, G.; Dua, K.; Garg, S. Acta Pharm. 2011, 61, 391
121. Cantera, R.; Leza, M.; Bachiller, C. J. Pharm. Sci. 2002, 91, 2240
122. Aitipamula, S.; Nangia, A. Polymorphism: Fundamentals and Applications. In Supramolecular Chemistry: From Molecules to Nanomaterials; Steed, J. W.,; Gale, P. A., Eds.; John-Wiley: New York, 2012; pp 2957-2974.
123. Zhang, J.; Tan, X.; Gao, J.; Fan, W.; Gao, Y.; Qian, S. J. Pharm. Pharmacol. 2013, 65, 44
124. Caira, M. R.; Bourne, S. A.; Samsodien, H.; Engel, E.; Liebenberg, W.; Stieger, N.; Aucamp, M. CrystEngComm 2012, 14, 2541
125. Blagden, N.; de Matas, M.; Gavan, P.; York, P. Adv. Drug Delivery Rev. 2007, 59, 617
126. Qiu, Y.; Chen, Y.; Liu, L.; Zhang, G. G. Z. Developing Solid Oral Dosage Forms: Pharmaceutical Theory and Practice, 1 st ed.; Academic Press: New York, 2009; p 75.
127. Hildebrand, J. H. Solubility; The Chemical Catalog Company: New York, 1924; p 206.
128. Newman, A. Org. Process Res. Dev. 2013, 17, 457
129. An, J.; Kim, W. Cryst. Growth Des. 2013, 13, 31
130. An, J.; Kim, J.; Chang, S.; Kim, W. Cryst. Growth Des. 2010, 10, 3044
131. McKellar, S. C.; Urquhart, A. J.; Lamprou, D. A.; Florence, A. J. ACS Comb. Sci. 2012, 14, 155
132. Lopez-Mejías, V.; Knight, J. L.; Brooks, C. L.; Matzger, A. J. Langmuir 2011, 27, 7575
133. Diao, Y.; Whaley, K. E.; Helgeson, M. E.; Woldeyes, M. A.; Doyle, P. S.; Myerson, A. S.; Hatton, T. A.; Trout, B. L. J. Am. Chem. Soc. 2012, 134, 673
134. Roy, S.; Matzger, A. J. Angew. Chem., Int. Ed. 2009, 48, 8505
135. Zencirci, N.; Gelbrich, T.; Kahlenberg, V.; Griesser, U. J. Cryst. Growth Des. 2009, 9, 3444
136. Kendrick, J.; Montis, R.; Hursthouse, M. B.; Leusen, F. J. J. Cryst. Growth Des. 2013, 13, 2906
137. Cornel, J.; Lindenberg, C.; Mazzotti, M. Cryst. Growth Des. 2009, 9, 243
138. Kraus, N.; Nolze, G. Powder Cell, A Program for Structure Visualization, Powder Pattern Calculation and Profile Fitting, version 2.3; Federal Institute for Materials Research and Testing: Berlin, Germany, 2000.