Fluconazole cocrystals with dicarboxylic acids

Crystal Growth and Design

Volumn 10, Issue 11, 2010, Pages 4943-4953

  Kastelic, Jože ^a   Hodnik, Žiga ^b   Šket, Primož ^c   Plavec, Janez ^c   Lah, Nina ^b   Leban, Ivan ^b   Pajk, Matjaž ^a   Planinšek, Odon ^b   Kikelj, Danijel ^b  

^a Krka Dd Novo Mesto   (Slovenia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

^c NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENTS; CO-CRYSTALS; DESIGN STRATEGIES; DICARBOXYLIC ACID; FLUCONAZOLE; GLUTARIC ACID; HYDROGEN BONDINGS; INTRAMOLECULAR INTERACTIONS; KEY ELEMENTS; PHYSICOCHEMICAL PROPERTY; SOLID STATE NMR; SOLUTION EVAPORATION; STRUCTURAL INFORMATION;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGEN BONDS;

EID: 78149346146     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg1010117     Document Type: Conference Paper

References (68)

1. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. In Solid-State Chemistry of Drugs, 2 nd ed.; SSCI Inc.: West Lafayette, IN, 1999.
2. Aakeröy, C. B.; Fasulo, M. E.; Desper, J. Mol. Pharmaceutics 2007, 4, 317-322
3. Morissette, S. L.; Almarson, 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, 275-300
4. Datta, S.; Grant, D. J. W. Nat. Rev. Drug Discovery 2004, 3, 42-57
5. Stahly, G. P. Cryst. Growth Des. 2007, 7, 1007-1026
6. Gardner, C. R.; Walsh, C. T.; Almarsson, Ö. Nat. Rev. Drug Discovery 2004, 3, 926-934
7. Huang, L.-F.; Tong, W.-Q. Adv. Drug Delivery Rev. 2004, 56, 321-334
8. Peterson, M. L.; Hickey, M. B.; Zaworotko, M. J.; Almarsson, O. J. Pharm. Pharm. Sci. 2006, 9, 317-326
9. Remenar, J. F.; Morisette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzman, H. R.; Almarsson, Ö. J. Am. Chem. Soc. 2003, 125, 8456-8457
10. Oswald, I. D. H.; Motherwell, W. D. S.; Parsons, S.; Pidcock, E.; Pulham, C. R. Crystallogr. Rev. 2004, 10, 57-66
11. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301-309
12. Shan, N.; Zaworotko, M. J. Drug Discov. Today 2008, 13, 440-446
13. Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448
14. Shan, N.; Zaworotko, M. J. Drug Discovery Today 2008, 13, 440-446
15. Childs, S. L.; Hardcastle, K. I. Cryst. Growth Des. 2007, 7, 1291-1304
16. Desiraju, R. G. CrystEngComm 2003, 5, 466-467
17. Dunitz, J. D. CrystEngComm 2003, 5, 506
18. Zukerman-Schpector, J.; Tiekink, E. R. T. Z. Kristallogr. 2008, 223, 233-234
19. Weyna, D. R.; Shattock, T.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2009, 9, 1106-1123
20. Friščić, T.; Jones, W. Cryst. Growth Des. 2009, 9, 1621-1637
21. Blagden, N.; Matas, M.; Gavan, P. T.; York, P. Adv. Drug Delivery Rev. 2007, 59, 617-630
22. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499-516
23. Sweetman, S. C. In Martindale: The Complete Drug Reference, 35 th ed.; Pharmaceutical Press: London, 2007; pp 479-481.
24. Alkhamis, K. A.; Obaidat, A. A.; Nuseirat, A. F. Pharm. Dev. Technol. 2002, 7, 491-503
25. Caira, M. R.; Alkhamis, K. A.; Obaidat, R. M. J. Pharm. Sci. 2004, 93, 601-611
26. Alkhamis, K. A.; salem, M. S.; Obaidat, R. M. J. Pharm. Sci. 2006, 95, 859-870
27. Park, H. J.; Kim, M.-S.; Lee, S.; Kim, J.-S.; Woo, J.-S.; Park, J.-S.; Hwang, S.-J. Int. J. Pharm. 2007, 328, 152-160
28. Desai, S. R.; Shaikh, M. M.; Dharwadkar, S. R. Therm. Acta 2003, 399, 81-89
29. Kreidl, J.; Czibula, L.; Szantay, C.; Farkas, J.; Deutschne-Juchasz, I.; Hegedus, I.; Werkne-Papp, E.; Nagyne-Bagdy, J.; Piller, A. WO Patent, WO02/076955 A1, 2002.
30. Product Monograph: Diflucan (fluconazole); Pfizer Canada Inc.: Kirkland, Quebec, 2004.
31. Stahl, H. P.; Wermuth, C. G. In Handbook of Pharmaceutical Salts-Properties, Selection and Use; Verlag Helvetica Chimica Acta: Zurich, 2002.
32. Childs, S. L.; Stahly, G. P.; Park, A. Mol. Pharmaceutics 2007, 4, 323-338
33. Fekete, P.; Virgula, J.; Furdyga, E.; Leventiszne, H. M.; Klebovich, I.; Baloghne, N. K., WO Patent, WO 2005/002553 A2, 2005.
34. Papageorgiou, G. Z.; Bikiaris, D.; Kanaze, F. I.; Kravas, E.; Stergiou, A.; Georgarakis, E. Drug Dev. Ind. Pharm. 2008, 34, 336-346
35. Vandercam, B.; Gibbs, D.; Valtonen, M.; JSger, H.; Armignacco, O. J. Int. Med. Res. 1998, 26, 209-218
36. McMahon, J.; Peterson, M.; Zaworotko, M. J.; Shattock, T.; Hickey, M. B. WO patent, WO 2006/007448 A2, 2006.
37. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
38. Sheldrick, G. M. SHELX97, Program for Crystal Structure Solution and Refinement; University of Göttingen: Germany, 1997.
39. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 1013-1021
40. Aakeröy, C. B.; Desper, J.; Fasulo, M. E. CrystEngComm 2006, 8, 586-588
41. Aakeröy, C. B.; Desper, J.; Scott, B. M. T. Chem. Commun. 2006, 8, 1445-1447
42. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; O'Donnell, E.; Park, A. Pharm. Res. 2006, 23, 1888-1897
43. Jagannathan, N. R.; Rao, C. N. R. Chem. Phys. Lett. 1987, 140, 46-50
44. Raymond, C; Rowe, R. C.; Sheskey, P. J.; Owen, S. C. In Handbook of Pharmaceutical Excipients, 5 th ed.; Pharmaceutical Press: London, 2005.
45. O'Neil, M. J. In The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14 th ed.; Merck Publishing, Rathway, NJ, 2006.
46. Bis, J. A.; Zaworotko, M. J. Cryst. Growth Des. 2005, 5, 1169-1179
47. Bis, J. B.; Vishweshwar, P.; Weyna, D.; Zaworotko, M. J. Mol. Pharmaceuics 2007, 4, 401-416
48. Mó, O.; de Paz, J. L. G.; Yáñez, M. J. Phys. Chem. 1986, 90, 5597-5604
49. Sigel, A.; Sigel, H. In Metal Ions in Biological Systems; Marcel Dekker, Inc.: New York, 1996; pp 327-328.
50. Reutzel-Edens, S. M. NMR crystallography and the elucidation of structure-property relationships in crystalline solids, In Engineering of Crystalline Materials Properties; Novoa, J. J., Eds.; Springer: New York, 2008; pp 351-374.
51. Harris, R. K. Solid State Sci. 2004, 6, 1025-1037
52. Braga, D.; Palladino, G.; Polito, M.; Rubini, K.; Grepioni, F.; Chierotti, M. R.; Gobetto, R. Chem.-Eur. J. 2008, 14, 10149-10159
53. Tishmack, P. A.; Bugay, D. E.; Byrn, S. R. J. Pharm. Sci. 2003, 92 (3) 441-474
54. Vogt, F. G.; Clawson, J. S.; Strohmeier, M.; Edwards, A. J.; Pham, T. N.; Watson, S. A. Cryst. Growth Des. 2009, 9, 921-937
55. Harris, R. K. Analyst 2006, 131, 351-373
56. Gobetto, R.; Nervi, C.; Chierotti, M. R.; Braga, D.; Maini, L.; Grepioni, F.; Harris, R. K.; Hodkinson, P. Chem.-Eur. J. 2005, 11, 7461-7471
57. Brunner, E.; Sternberg, U. J. Prog. NMR Spectrosc. 1998, 32, 21-57
58. Emmler, T; Gieschler, S.; Limbach, H. H.; Buntkowsky, G. J. Mol. Struct. 2004, 700, 29-38
59. Sharif, S.; Schagen, D.; Toney, M. D.; Limbach, H. H. J. Am. Chem. Soc. 2007, 129, 4440-4455
60. Limbach, H.-H.; Pietrzak, M.; Sharif, S.; Tolstoy, P. M.; Shenderovich, I. G.; Smirnov, S. N.; Golubev, N. S.; Denisov, G. S. Chem.-Eur. J. 2004, 10, 5195-5204
61. Steiner, T. J. Phys. Chem. A 1998, 102, 7041-7052
62. Day, G. M.; Trask, A. V.; Motherwell, D. S.; Jones, W. Chem. Commun. 2006, 54-56
63. Ilczyszyn, M.; Gozisz, D.; Ilczyszyn, M. M. Spectrochim. Acta Part A 2003, 59, 1815-1828
64. Cyr, T. D.; Dawson, G. A.; Neville, G. A.; Shurvell, H. F. J. Pharm. Biomed. Anal. 1996, 14, 247-255
65. Barry, J. E.; Finkelstein, M.; Ross, D. J. Org. Chem. 1988, 53, 6058-6061
66. Braga., D.; Grepioni, F.; Desiraju, G. R. J. Organomet. Chem. 1997, 548, 33-43
67. Desiraju, G. R.; Steiner, T. The weak hydrogen bond in structural chemistry and biology, In IUCr Monographs on Crystallography No. 9; Oxford University Press Inc.: New York, 1999.
68. Flakus, H. T.; Miros, A. J. Mol. Struct. 1999, 484, 103-115