journal article·2007-06-01Open access

Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

G. Patrick Stahly

Crystal Growth & Design· Volume 7· Issue 6

Abstract

A detailed description of polymorph screening procedures is presented. On the basis of the results of 245 polymorph screens, organic compounds were found to exist in multiple solid forms quite frequently. About 90% exhibited multiple crystalline and noncrystalline forms; about 50% exhibited polymorphism. Cocrystals are defined, and cocrystal screening is discussed. Data from 64 cocrystal screens show that cocrystals were found in 61% of the cases, and the total number of cocrystals found was 192.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Crystallography and molecular interactions · Crystallization and Solubility Studies · Chemical Thermodynamics and Molecular Structure

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

SSCI, an Aptuit Company, 3065 Kent Avenue, West Lafayette, Indiana 47906

References (100+)

Show source-provided references
1. Bernstein J. · 2002
2. Berzelius J. · Jahresbericht · 1844 · 23 · 55
3. Sirota N. N. · Cryst. Res. Technol. · 1982 · 17 · 691
4. Lide, D. R. Ed.CRC Handbook of Chemistry and Physics, 81st ed.; CRC Press: Boca Raton, 2000; pp 4-1−4-36.
5. Corrosion Club · 2006
6. National Museum of Denmark, Conservation Department. · 2006
7. Indium Corporation · 2006
8. Wikipedia · 2006
9. Haleblian J. · J. Pharm. Sci. · 1969 · 58 · 92910.1002/jps.2600580802 ↗
10. Chemburkar S. R. · Org. Proc. Res. Dev. · 2000 · 4 · 41710.1021/op000023y ↗
11. International Conference on Harmonisation; Guidance on Q6A Specifications: Test Procedures and Acceptance Criteria for New Drug Substances and New Drug Products: Chemical Substances, 65 Fed. Reg. 83046 (December 29, 2000).
12. Miyazaki S. · Chem. Pharm. Bull. · 1974 · 22 · 642
13. Bauer J. · Pharm. Res. · 2001 · 18 · 86610.1023/A:1011052932607 ↗
14. Price S. L. · Adv. Drug Delivery Rev. · 2004 · 56 · 31910.1016/j.addr.2003.10.006 ↗
15. Hilfiker R. · 2006
16. Physical Characterization of Pharmaceutical Solids; Brittain, H. G., Ed.; Drugs and the Pharmaceutical Sciences Series Vol. 70; Marcel Dekker, Inc. New York, 1995.
17. Guillory J. K. · 1999
18. Hilfiker R. · 2006
19. Kofler L. · Ber. Dtsch. Chem. Ges. · 1943 · 76 · 72210.1002/cber.19430760715 ↗
20. Bouzard D. · 1985
21. Barnes R. D. · 1988
22. The Merck Index, 13th ed.; Merck & Co., Inc. Whitehouse Station, NJ, 2001; p 606.
23. Ward N. · 1999
24. 1997
25. Tros de Ilarduya M. C. · J. Pharm. Sci. · 1997 · 86 · 5110.1021/js9601748 ↗
26. Cross W. I. · Cryst. Growth Des. · 2003 · 3 · 15810.1021/cg025589n ↗
27. Hilden J. L. · Cryst. Growth Des. · 2003 · 3 · 92610.1021/cg034061v ↗
28. Chyall L. J. · Cryst. Growth Des. · 2002 · 2 · 51010.1021/cg0200311 ↗
29. Childs S. L. · Cryst. Growth Des. · 2004 · 4 · 44910.1021/cg034243p ↗
30. Kuhnert-Brandstätter M. · 1971
31. Nichols G. · J. Pharm. Sci. · 1998 · 87 · 69310.1021/js970483d ↗
32. Burger A. · Acta Pharm. Technol. · 1982 · 28 · 20
33. Peterson M. L. · J. Am. Chem. Soc. · 2002 · 124 · 10959
34. Chongprasert S. · J. Pharm. Sci. · 1998 · 87 · 116010.1021/js970342b ↗
35. Hilfiker R. · 200610.1002/3527607889 ↗
36. Hilfiker R. · 200610.1002/3527607889 ↗
37. Landers · 2004 · A1
38. Morisette S. L. · Adv. Drug Delivery Rev. · 2004 · 56 · 300
39. Frank C. F. · 1999 · 225
40. Hilfiker R. · 2006 · 297
41. Ivanisevic I. · J. Phys. Chem. B · 2005 · 109 · 778710.1021/jp0455935 ↗
42. Barr G. · J. Appl. Crystallogr. · 2004 · 37 · 65410.1107/S0021889804009859 ↗
43. Smith D. K. · 1989 · 190
44. The Rietveld Method; Young, R. A., Ed.; IUCr Monographs on Crystallography 5; Oxford University Press: Oxford, 1993.
45. David W. I. F. · Chem. Commun. · 1998 · 931 · 932
46. Burger A. · Mikrochim. Acta · 1979 · 272
47. Burger A. · Mikrochim. Acta · 1979 · 316
48. Friedel G. · Bull. Soc. Franc. Mineral. · 1907 · 30 · 326
49. Donnay G. D. H. · Am. Mineral. · 1937 · 22 · 446
50. Dowty E. · Am. Mineral. · 1980 · 65 · 465
51. Henck J-O · J. Pharm. Sci. · 1999 · 88 · 108
52. Dunitz J. D. · Acc. Chem. Res. · 1995 · 28 · 20010.1021/ar00052a005 ↗
53. Henck J-O · J. Am. Chem. Soc · 2001 · 123 · 1841
54. Jones P. G. · Chem. Br. · 1981 · 17 · 225
55. Stephenson G. A. · J. Pharm. Sci. · 1997 · 86 · 1244
56. Byrn S. R. · 1999
57. Huang L-F · Adv. Drug Delivery Rev. · 2004 · 56 · 344
58. Yalkowsky, S. H.Solubility and Solubilization in Aqueous Media; American Chemical Society: Washington, DC and Oxford University Press: New York, 1999; p 83.
59. 2003
60. Ticehurst M. D. · Int. J. Pharm. · 2002 · 247 · 1010.1016/S0378-5173(02)00277-6 ↗
61. SmithKline Beecham Corp. · 2003
62. Threlfall T. · Org. Proc. Res. Dev. · 2000 · 4 · 39010.1021/op000058y ↗
63. Gu C-H · J. Pharm. Sci. · 2001 · 90 · 1890
64. Carstensen J. T. · Drug Dev. Ind. Pharm. · 1995 · 21 · 53610.3109/03639049509048120 ↗
65. Bernstein J. · 2002
66. McConnell J. F. · Cryst. Struct. Commun. · 1974 · 3 · 73
67. Shankland N. · Chem. Commun. · 1996 · 855 · 856
68. (c) Shankland, N.; Wilson, C. C.; Florence, A. J.; Cox, P. J.Acta Crystallogr., Sect. C: Cryst. Struct.Commun.1997,53, 951−954.10.1107/S0108270197003193 ↗
69. Deffet L. · 1942
70. Giron D. · Thermochim. Acta · 1995 · 248 · 5910.1016/0040-6031(94)01953-E ↗
71. Bernstein J. · 2002
72. Gavezzotti A. · J. Am. Chem. Soc. · 1995 · 117 · 1230510.1021/ja00154a032 ↗
73. Cambridge Crystallographic Data Centre, Statistics.http://www.ccdc.cam.ac.uk/products/csd/statistics/(accessed August 28, 2006).
74. Griesser U. J. · 1999
75. Bernstein J. · 2002 · 14
76. Henck J-O · Pharm. Ind. · 1997 · 59 · 169
77. Grunenberg A. · Pharmazie · 1997 · 26 · 231
78. Lohani S. · 2006 · 21
79. Stahly G. P. · 2003
80. Morris K. R. · 1999
81. Seth A. R. · Cryst. Growth Des. · 2005 · 5 · 578
82. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G.Solid-State Chemistry ofDrugs, 2nd ed.; SSCI, Inc. West Lafayette, IN, 1999; p 24.
83. Bingham A. · Chem. Commun. · 2001 · 603 · 604
84. Seddon K. · R Cryst. Growth Des. · 2004 · 4 · 108710.1021/cg030084y ↗
85. Bernstein J. · Cryst. Growth Des. · 2005 · 5 · 166210.1021/cg058007l ↗
86. Desiraju G. R. · Cryst. Growth Des. · 2004 · 4 · 109010.1021/cg030085q ↗
87. Nangia A. · Cryst. Growth Des. · 2006 · 6 · 410.1021/cg050343e ↗
88. Brittain H. G. · Spectroscopy · 2000 · 15 · 39
89. Deshpande P. K.
90. Byrn, S. R.Solid-State Chemistry of Drugs; Academic Press: New York, 1982; pp 7−10.
91. Dunitz J. D. · CrystEngComm · 2003 · 5 · 50610.1039/b315687g ↗
92. Desiraju G. R. · CrystEngComm · 2003 · 5 · 46610.1039/b313552g ↗
93. Wilson, K. G.The Columbia Guide to Standard American English; MJF Books: New York, 1993; p 99.
94. Aakeröy C. B. · J. CrystEngCommun · 2005 · 7 · 448
95. Bernstein J. · Chem. Commun. · 2005 · 5007 · 5012
96. Almarsson · J. Chem. Commun. · 2004 · 1889 · 1896
97. Vishweshwar P. · J. Pharm. Sci. · 2006 · 95 · 51610.1002/jps.20578 ↗
98. Steiner T. · Angew. Chem., Int. Ed. · 2001 · 40 · 265410.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L ↗
99. The Merck Index, 13th ed.; O'Neil, M. J., Sr. Ed.; Merck & Corp., Inc. Whitehouse Station, NJ, 2001; p 81.
100. Ling A. R. · J. Chem. Soc. · 1893 · 63 · 132710.1039/CT8936301327 ↗