Saccharin salts of active pharmaceutical ingredients, their crystal structures, and increased water solubilities

Crystal Growth and Design

Volumn 5, Issue 6, 2005, Pages 2299-2309

  Banerjee, Rahul ^a   Bhatt, Prashant M ^a   Ravindra, Nittala V ^b   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b GVK BIOSCIENCES PVT LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27744484364     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg050125l     Document Type: Article

References (86)

1. (a) Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid-State Chemistry of Drugs, 2nd ed.; SSCI Inc.: West Lafayette, IN, 1999.
2. (b) Brittain, H. G. Methods for the Characterization of Polymorphs and Solvates. In Polymorphism in Pharmaceutical Solids; Brittain, H. G., Ed.; Marcel Dekker Inc.: New York, 1999.
3. (c) Dutta, S., Grant, D. J. W. Nat. Rev. Drug Discovery 2004, 3, 42.
4. (a) Morris, K. R.; Rodriguez-Hornedo, N. Encyclopedia of Pharmaceutical Technology; Marcel Dekker: New York, 1993.
5. (b) Morissette, S. L.; Almarsson, Ö.; Peterson, M. L.; Remenar, J. F.; Read, M. J.; Lemmo, A. V.; Ellis, S.; Cima, M. J.; Gardner, C. R. Adv. Drug Delivery Rev. 2004, 56, 275.
6. Selected recent references to API polymorphs include. (a) Bernstein, J. Polymorphism in Molecular Crystals; Clarendon Press: Oxford, 2002.
7. (b) Price, C. P.; Grzesiak, A. L.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 5512.
8. (c) Hulme, A. T.; Price, S. L.; Tocher, D. A. J. Am. Chem. Soc. 2005, 127, 1116.
9. (d) Trask, A. V.; Shan, N.; Motherwell, W. D.; Jones, W.; Feng, S.; Tan, R. B.; Carpenter, K. J. Chem Commun. 2005, 880.
10. (e) Grant, D. J. W.; Byrn S. R. Adv. Drug Delivery Rev. 2004, 56, 237.
11. (f) Coste, S.; Schneider, J.-M.; Petit, M.-N.; Coquerel, G. Cryst. Growth Des. 2004, 4, 1237.
12. (g) Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, 890.
13. (h) Bonnet, P. A.; van de Streek, J.; Trask, A. V.; Motherwell, W. D. S.; Jones, W. CrystEngComm 2004, 6, 535.
14. (i) Caira, M. R.; Bourne, S. A.; Mhlongo, W. T.; Dean, P. M. Chem. Commun. 2004, 2216.
15. (j) Grzesiak, A. L.; Lang, M.; Kim, K.; Matzger, A. J. J. Pharm. Sci. 2003, 92, 2260.
16. (k) Cross, W. I.; Blagden, N.; Davey, R. J.; Pritchard, R. G.; Neumann, M. A.; Roberts, R. J.; Rowe, R. C. Cryst. Growth Des. 2003, 3, 151.
17. (l) Davey, R. J. Chem. Commun. 2003, 1463.
18. (m) Peterson, M. L.; Morissette, S. L.; McNulty, C.; Goldsweig, A.; Shaw, P.; LeQuesne, M.; Monagle, J.; Encina, N.; Marchionna, J.; Johnson, A.; Cima, M. J.; Almarsson, Ö. J. Am. Chem. Soc. 2002, 124, 10958.
19. (n) Suryanarayanan, R.; Byrn, S. R. Adv. Drug Delivery Rev. 2001, 48, 1. Selected recent references to API pseudopolymorphs, solvates, and hydrates include
20. (o) Kim, Y.-S.; Rousseau. R. W. Cryst. Growth Des. 2004, 4, 1211.
21. (p) Hosokawa, T.; Datta, S.; Sheth, A. R.; Brooks, N. R.; Young, V. G.; Grant, D. J. W. Cryst. Growth Des. 2004, 4, 1195.
22. (q) Gillon, A. L.; Feeder, N.; Davey, R. J.; Storey, R. Cryst. Growth Des. 2003, 3, 663.
23. (r) Garnier, S.; Petit, S.; Coquerel, G. J. Therm. Anal. Calorim. 2002, 68, 489.
24. (s) Bingham, A. L.; Hughes, D. S.; Hursthouse, M. B.; Lancaster, R. W.; Tavener, S.; Threlfall, T. L. Chem. Commun. 2001, 7, 603.
25. (t) Nangia, A.; Desiraju, G. R. Chem. Commun. 1999, 7, 605. Selected recent references to API salts include
26. (u) Remenar, J. F.; MacPhee, J. M.; Larson, B. K.; Tyagi, V. A.; Ho, J. H.; McIlroy, D. A.; Hickey, M. B.; Shaw, P. B.; Almarsson, Ö. Org. Proc. Res. Dev. 2003, 7, 990.
27. (v) Bastin, R. J.; Bowker, M. J.; Slater, B. J. Org. Proc. Res. Dev. 2000, 4, 427. Selected recent references to API cocrystals include
28. (w) Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzman, H. R.; Almarsson, Ö. J. Am. Chem. Soc. 2003, 125, 8456.
29. (x) Walsh, R. D.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 186.
30. Tremblay, J.-F. Chem. Eng. News 2005, 83(2), 15.
31. (a) Gu, C. H.; Grant, D. J. W. In Handbook of Experimental Pharmacology: Stereochemical Aspects of Drug Action and Disposition; Eichelbaum, M., Testa, B., Somogyi, A., Eds.; Springer, Berlin, 2003.
32. (b) Puddipeddi, M.; Serajuddin, A. T. M.; Grant, D. J. W.; Stahl, P. H. In Handbook of Pharmaceutical Salts: Properties, Selection, and Use; Stahl, P. H., Wermuth, C. G., Eds.; Wiley, Weinheim, 2002; pp 19-38.
33. (c) Neau, S. H. In Water-Insoluble Drug Formations; Liu, R., Ed.; Interpharm: Buffalo Grove, 2000; pp 405-425.
34. (d) Berge, S. M.; Bighley, L. D.; Monkhouse, D. C. J. Pharm. Sci. 1977, 66, 1.
35. Poor solubility of the parent API (free acid or free base) is a long-standing problem. More than 40% of newly discovered drugs have little or no water solubility (less than 0.1 mg/ mL).
36. Räder, K.; Stoss, P. U.S. publication no., US 4362730, 07/ 12/1982.
37. Rayburn, J. W. International publication no., WO 00/12067, 09/03/2000.
38. Even when increased solubility increases bioavailability it may not lead to a desired situation. For example, see Schwalbe, C. H. Cryst. Rev. 2005, 11, 49.
39. The use of saccharin as a sweetener of food stuffs is very extensive, and a review of this aspect is beyond the scope of the present paper.
40. Bhatt, P. M.; Ravindra, N. V.; Banerjee, R.; Desiraju, G. R. Chem. Commun. 2005, 1073.
41. Pseudoephedrine and haloperidol gave the anhydrous 1:1 saccharinates upon grinding with saccharin in 100% yield and uncontaminated by other solid forms. All the other APIs posed problems during grinding to a greater or lesser extent.
42. SMART, Version 5.05; Bruker AXS, Inc.: Madison, Wisconsin, 1998.
43. SAINT, Version 6.2, Bruker AXS, Inc.: Madison, Wisconsin, 2001.
44. Sheldrick, G. M. SHELXTL V5.1; Madison, WI, 1998.
45. 2.3. Kraus, N.; Nolze, G. POWDER CELL, version 2.3; Federal Institute for Materials Research and Testing: Berlin, Germany, 2000.
46. Glomme, A.; Marz, J.; Dressman, J. B. J. Pharm. Sci. 2005, 94, 1.
47. Ward, S. C.; Hursthouse, M. B.; Woods, D. C.; Lewis, S. M. Systematic Study into the Salt Formation of Functionalised Organic Substrates, http://www.nesc.ac.uk/events/ahm2003/ AHMCD/pdf/040.pdf.
48. Selected recent references on cocrystals include (a) Trask, A. V.; Jones W. In Top. Curr. Chem. 2005, 41-70.
49. (b) Gao, X.; Friscic, T.; MacGillivray, L. R. Angew. Chem. Int. Ed. 2004, 43, 232.
50. (c) Ma, B. Q.; Coppens, P. Cryst. Growth Des. 2004, 4, 211.
51. (d) Olenik, B.; Smolka, T.; Boese, R.; Sustmann, R. Cryst. Growth Des. 2003, 3, 183.
52. (e) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A.; Nieuwenhuyzen, M. Cryst. Growth Des. 2003, 3, 159.
53. (f) Bhogala, B. R.; Nangia, A. Cryst. Growth Des. 2003, 3, 547.
54. (g) Reddy, L. S.; Nangia, A.; Lynch, V. M. Cryst. Growth Des. 2004, 4, 89.
55. Even three components have been assembled together in a cocrystal, but this is a very delicate exercise. See (a) Bhogala, B. R.; Basavoju, S.; Nangia, A. Cryst. Growth Des. 2005, 5, 1683.
56. (b) Aakeröy, C. B.; Desper, J.; Urbina, J. F. Chem. Commun. 2005, 2820.
57. (c) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240.
58. Fleischman, S. G.; Kuduva, S. S.; McMahon, J. A.; Moulton, B.; Walsh, R. B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Cryst. Growth Des. 2003, 3, 909.
59. Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889.
60. Seeman, P.; Lee, T.; Chau-Wong, M.; Wong, K. Nature 1976, 261, 717.
61. Kanfer, I.; Dowse, R.; Vusumuzi, V. Pharmacotherapy 1993, 13, 116S.
62. (a) van Leeuwen, R.; Katlama, C.; Kitchen V. J. Infect. Dis. 1995, 171, 1166
63. (b) Yuen, G. J.; Morris, D. M.; Mydlow, P. K. J. Clin. Pharmacol. 1995, 35, 1174.
64. (a) Grant, S.; Fitton, A. Drugs 1994, 48, 253.
65. (b) Cohen, L. J. Pharmacotherapy 1994, 14, 253.
66. Peeters, O. M.; Blaton, N. M.; Ranter, C. J. Acta Crystallogr., Sect. C. 1993, 49, 1698.
67. (a) Murdoch, D.; McTavish, D. Drugs 1992, 44, 604.
68. (b) Koe, B. K.; Weissman, A.; Welch, W. M. J. Pharmacol. Exp. Ther. 1983, 226, 686.
69. (a) Clerc, G. E.; Ruimy, P.; Verdeau-Pailles, J. Int. Clin. Psychopharmacol. 1994, 9, 139.
70. Oosterbaan, M. J. M.; Keltjens, R. International publication no., U.S. 20030190353 A1, 09/10/2003.
71. (a) Langtry, H. D.; Benfield, P. Drugs 1990, 40, 291.
72. (b) Hoehns, J. D.; Perry, P. J. Clin. Pharm. 1993, 12, 881.
73. (a) Burges, R. A. J. Hum. Hypertens. 1991, 5, 49.
74. (b) Murdoch, D.; Heel, R. C. Drugs 1991, 41, 478.
75. Sheth, A. R.; Bates, S.; Muller, F. X.; Grant, D. J. W. Cryst. Growth Des. 2004, 4, 1091.
76. Boldyrev, V. V. J. Mat. Sci. 2004, 39, 5117.
77. Banerjee, R.; Bhatt, P. M.; Kirchner, M. T.; Desiraju, G. R. Angew. Chem., Int. Ed. 2005, 44, 2515.
78. Kinbara, K.; Saigo, K. In Topics in Stereochemistry; Denmark, S. E., Ed.; Wiley: New York, 2003; pp 207-265.
79. In this case, the solvation energy for both salts in the pair should be the same or very similar. Therefore, solubility differences can be directly correlated with differences in crystal packing.
80. (a) Sivalakshmidevi, A.; Vyas, K.; Rao, S. M.; Reddy G. O. Acta Crystallogr., Sect. E 2002, 58, 1072.
81. (b) Vega, D.; Fernandez, D.; Echeverria, G. Acta Crystallogr., Sect. E 2000, 56, 1009.
82. Rao, S. M.; Vyas, K.; Sivalakshmidevi, A.; Reddy, G. O. International Patent Appl. No. WO02/46140 A1, June 13, 2002.
83. a = 13.94) and carbamazepine/saccharin 1:1 cocrystal and found both of them to be practically insoluble in water.
84. (a) Zaworotko, M. J.; Moulton, B.; Rodriguez-Hornedo, N. International publication no., WO 03/074474 A2, 12/09/2003.
85. (b) Almarsson, Ö.; Zaworotko, M. J. International publication no., WO. 2004/078161 A1, (16/09/2004).
86. (c) Childs, S. L. International publication no., WO 2004/064762 A2, 05/08/2004.