Supramolecular architectures of meloxicam carboxylic acid cocrystals, a crystal engineering case study

Crystal Growth and Design

Volumn 10, Issue 10, 2010, Pages 4401-4413

  Cheney, Miranda L ^a,b   Weyna, David R ^a,b   Shan, Ning ^a   Hanna, Mazen ^a   Wojtas, Lukasz ^b   Zaworotko, Michael J ^b  

^a Thar Pharmaceuticals Inc   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-HYDROXY-2-NAPHTHOIC ACID; AQUEOUS SOLUBILITY; CO-CRYSTALS; COCRYSTAL STRUCTURE; FUMARIC ACIDS; GLUTARIC ACID; HIGH PERMEABILITY; L-MALIC ACID; MELOXICAM; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PHARMACOLOGICAL PROPERTIES; SALICYLIC ACIDS; SOLUTION METHODS; SUCCINIC ACIDS; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR SYNTHONS; THERMAL ANALYSIS;

CARBOXYLIC ACIDS; CRYSTAL ENGINEERING; DRUG PRODUCTS; THERMOANALYSIS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

SUPRAMOLECULAR CHEMISTRY;

EID: 77957712715     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg100514g     Document Type: Conference Paper

References (83)

1. Allen, L. V.; Popovich, N. G.; Ansel, H. C., Ansel's pharmaceutical dosage forms and drug delivery systems; Lippincott Williams and Wilkins: Baltimore, MD, 2005.
2. Byrn, S. R.; Pfeiffer, R. R.; Stephenson, G.; Grant, D. J. W.; Gleason, W. B. Chem. Mater. 1994, 6, 1148
3. Haleblian, J. K. J. Pharm. Sci. 1975, 64, 1269
4. Berge, S. M.; Bighley, L. D.; Monkhouse, D. C. J. Pharm. Sci. 1977, 66, 1
5. Dublin, C. H. Drug Delivery Technol. 2006, 6, 34
6. Khankari, R. K.; Grant, D. J. W. Thermochim. Acta 1995, 248, 61
7. Vippagunta, S. R.; Brittain, H. G.; Grant, D. J. W. Adv. Drug Delivery Rev. 2001, 48, 3
8. Zaworotko, M.; Arora, K. Pharmaceutical co-crystals: A new opportunity in pharmaceutical science for a long-known but little studied class of compounds. In Polymorphism in Pharmaceutical Solids, 2 nd ed.; Brittain, H. G., Ed.; Informa Healthcare: London, 2009.
9. Aaltonen, J.; Alleso, M.; Mirza, S.; Koradia, V.; Gordon, K. C.; Rantanen, J. Eur. J. Pharm. Biopharm. 2009, 71, 23
10. Yin, S. X.; Grosso, J. A. Curr. Opin. Drug Discovery Dev. 2008, 11, 771
11. Cheney, M. L.; Shan, N.; Healey, E. R.; Hanna, M.; Wojtas, L.; Zaworotko, M. J.; Sava, V.; Song, S.; Sanchez-Ramos, J. R. Cryst. Growth Des. 2010, 10, 394
12. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311
13. Pepinsky, R. Phys. Rev. 1955, 100, 971
14. Desiraju, G. R., Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
15. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647
16. Shan, N.; Batchelor, E.; Jones, W. Tetrahedron Lett. 2002, 43, 8721
17. Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9
18. Shan, N.; Bond, A. D.; Jones, W. Tetrahedron Lett. 2002, 43, 3101
19. Shan, N.; Jones, W. Tetrahedron Lett. 2003, 44, 3687
20. Bis, J. A.; Vishweshwar, P.; Weyna, D.; Zaworotko, M. J. Mol. Pharmaceutics 2007, 4, 401
21. Shattock, T. R.; Arora, K. K.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2008, 8, 4533
22. Allen, F. H. Acta Crystallogr. 2002, B58, 380
23. Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889
24. Shan, N.; Zaworotko, M. J. Drug Discovery Today 2008, 13, 440
25. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. J. Am. Chem. Soc. 2004, 126, 13335
26. Banerjee, R.; Bhatt, P. M.; Ravindra, N. V.; Desiraju, G. R. Cryst. Growth Des. 2005, 5, 2299
27. Good, D. J.; Rodriguez-Hornedo, N. Cryst. Growth Des. 2009, 9, 2252
28. Karki, S.; Friscic, T.; Fabian, L.; Laity, P. R.; Day, G. M.; Jones, W. Adv. Mater. 2009, 21, 3905
29. Shan, N.; Toda, F.; Jones, W. Chem. Commun. 2002, 2372
30. Weyna, D. R.; Shattock, T.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2009, 9, 1106
31. Friščić, T.; Childs, S. L.; Rizvi, S. A. A.; Jones, W. CrystEngComm 2009, 11, 418
32. Lu, E.; Rodriguez-Hornedo, N.; Suryanarayanan, R. CrystEngComm 2008, 10, 665
33. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzman, H. R.; Almarsson, O. J. Am. Chem. Soc. 2003, 125, 8456
34. Basavoju, S.; Bostrom, D.; Velaga, S. P. Cryst. Growth Des. 2006, 6, 2699
35. Chen, A. M.; Ellison, M. E.; Peresypkin, A.; Wenslow, R. M.; Variankaval, N.; Savarin, C. G.; Natishan, T. K.; Mathre, D. J.; Dormer, P. G.; Euler, D. H.; Ball, R. G.; Ye, Z. X.; Wang, Y. L.; Santos, I. Chem. Commun. 2007, 419
36. Remenar, J. F.; Peterson, M. L.; Stephens, P. W.; Zhang, Z.; Zimenkov, Y.; Hickey, M. B. Mol. Pharmaceutics 2007, 4, 386
37. Zegarac, M.; Mestrovic, E.; Dumbovic, A.; Devcic, M.; Tudja, P. Pharmaceutically Acceptable Co-Crystalline Forms of Sildenafil, WO 2007/080362 A1, 2007.
38. Childs, S. L.; Rodríguez-Hornedo, N.; Reddy, L. S.; Jayasankar, A.; Maheshwari, C.; McCausland, L.; Shipplett, R.; Stahly, B. C. CrystEngComm 2008, 10, 856
39. Shiraki, K.; Takata, N.; Takano, R.; Hayashi, Y.; Terada, K. Pharm. Res. 2008, 25, 2581
40. Stanton, M. K.; Bak, A. Cryst. Growth Des. 2008, 8, 3856
41. Stanton, M. K.; Tufekcic, S.; Morgan, C.; Bak, A. Cryst. Growth Des. 2009, 9, 1344
42. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 1013
43. Ahmed, M.; Khanna, D.; Furst, D. E. Exp. Opin. 2005, 1, 739
44. Thompson, J. P.; Sharpe, P.; Kiani, S.; Owen-Smith, O. Br. J. Anaesth. 2000, 84, 151
45. Roughan, J. V.; Flecknell, P. A. Eur. J. Pain 2003, 7, 397
46. Engelhardt, G.; Homma, D.; Schlegel, K.; Utzmann, R.; Schnitzler, C. Inflammation Res. 1995, 44, 423
47. Stei, P.; Kruss, B.; Wiegleb, J.; Trach, V. Br. J. Rheumatol. 1996, 35 (Suppl. 1) 44
48. Lehmann, H. A.; Baumeister, M.; Luetzen, L.; Wiegleb, J. Inflammopharmacology 1996, 4, 105
49. Burdan, F. Toxicology 2005, 211, 12
50. Harirforoosh, S.; Aghazadeh-Habashi, A.; Jamali, F. Clin. Exp. Pharmacol. Physiol. 2006, 33, 917
51. Seedher, N.; Bhatia, S. AAPS PharmSciTech 2003, 4 33
52. Takagi, T.; Ramachandran, C.; Bermejo, M.; Yamashita, S.; Yu, L. X.; Amidon, G. L. Mol. Pharmaceutics 2006, 3, 631
53. Luger, P.; Daneck, K.; Engel, W.; Trummlitz, G.; Wagner, K. Eur. J. Pharm. Sci. 1996, 4, 175
54. Coppi, L.; Sanmarti, M. B.; Clavo, M. C. Crystalline Forms of Meloxicam and Processes for Thier Preparation and Interconversion, US Patent 6,967,248 B2, 2005.
55. Davies, N. M.; Skjodt, N. M. Clin. Pharmacokinet. 1999, 36, 115
56. Ghorab, M. M.; Abdel-Salam, H. M.; El-Sayad, M. A.; Mekhel, M. M. AAPS PharmSciTech 2004, 5 59
57. Han, H. K.; Choi, H. K. Eur. J. Pharm. Biopharm. 2007, 65, 99
58. Defazio, S.; Cini, R. J. Chem. Soc., Dalton Trans. 2002, 1888
59. Bock, T.; Saegmueller, P.; Sieger, P.; Tuerck, D. Meloxicam for Oral Administration. US Patent 6,869,948 B1, 2005.
60. Struengmann, A.; Freudensprung, B.; Klokkers, K. New Pharmaceutical Compositions of Meloxicam with Improved Solubility and Bioavailability, International Patent WO 99/09988 A1, 1999.
61. Meloxicam for this study was purchased as form I, which was stable at ambient conditions throughout the study.
62. Myz, S. A.; Shakhtshneider, T. P.; Fucke, K.; Fedotov, A. P.; Boldyreva, E. V.; Boldyrev, V. V.; Kuleshova, N. I. Mendeleev Commun. 2009, 19, 272
63. Childs, S. L.; Hardcastle, K. I. Cryst. Growth Des. 2007, 7, 1291
64. Bruker SMART, SAINT-Plus, SADABS, XP and SHELXTL; Bruker: Madison, WI, 1997.
65. Sheldrick, G. M. SHELXTL, University of Göttingen: Göttingen, Germany, 1997.
66. It must be noted that the CSD structures have not been systematically populated to provide a balanced representation of the various functional groups. Although the supramolecular synthon approach has been successfully used in the various pharmaceutical cocrystal studies, the CSD statistical result here could be biased.
67. Fabiola, G. F.; Pattabhi, V.; Manjunatha, S. G.; Rao, G. V.; Nagarajan, K. Acta Crystallogr. 1998, C54, 2001
68. CSD version 5.31, November 2009 release including May 2010 update. Search parameters: organics only, 3D coordinates determined, R < 7.5%.
69. Etter, M. C. Acc. Chem. Res. 1990, 23, 120
70. Ki, H. M.; Choi, H. K. Arch. Pharm. Res. 2007, 30, 215
71. Stahl, P. H.; Wermuth, C. G., Handbook of Pharmaceutical Salts: Properties, Selection, and Use; WILEY-VCH: Zurich, 2002.
72. Bhogala, B. R.; Basavoju, S.; Nangia, A. CrystEngComm 2005, 7, 551
73. Delori, A.; Suresh, E.; Pedireddi, V. R. Chem.-Eur. J. 2008, 14, 6967
74. Childs, S. L.; Stahly, G. P.; Park, A. Mol. Pharmaceutics 2007, 4, 323
75. a values is straightforward but also could be less rigorous. However, confirmation of relevant proton locations in 8, 9, and 11 - 20 remains inconclusive using available characterization techniques. As part of the continuous study, further attempts of single-crystal XRD characterization for 8, 9, and 11 - 20 are being undertaken.
76. Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectroscopic Identification of Organic Compounds; John Wiley & Sons: New York, 2005.
77. a Data, http://research.chem.psu.edu/brpgroup/pKa- compilation.pdf.
78. Minnick, L. J.; Kilpatrick, M. J. Phys. Chem. 1939, 43, 259
79. Chemical Dictionary Online, 1-Hydroxy-2-naphthoic acid. http://www.chemicaldictionary.org/dic/1/1-Hydroxy-2-naphthoic-acid-919.html (August 2009)
80. Brittain, H. G.; Prankerd, R. J. Profiles of drug substances, excipients, and related methodolgy; Academic Press: New York, 2007; p 369
81. Cabelli, D. E.; Bielski, B. H. J. Z. Naturforsch., B 1985, 40, 1731
82. Erdemgil, F. Z.; Sanli, S.; Sanli, N.; Özkan, G.; Barbosa, J.; Guiteras, J.; Beltrán, J. L. Talanta 2007, 72, 489
83. Castro, J. L.; Ramírez, M. R. L.; Tocón, I. L.; Otero, J. C. J. Raman Spectrosc. 2002, 33, 455