Soluble cocrystals of the xanthine oxidase inhibitor febuxostat

Crystal Growth and Design

Volumn 13, Issue 7, 2013, Pages 3188-3196

  Maddileti, D ^a   Jayabun, S K ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COCRYSTAL STRUCTURE; DISSOLUTION RATES; HUMIDITY CONDITIONS; P-AMINOBENZOIC ACID; PHYSICO-CHEMICAL CHARACTERIZATION; POWDER X RAY DIFFRACTION; X RAY CRYSTAL STRUCTURES; XANTHINE OXIDASE;

DIFFERENTIAL SCANNING CALORIMETRY; HYDROGEN BONDS; SUGAR SUBSTITUTES; UREA; X RAY DIFFRACTION;

AMIDES;

EID: 84879860140     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg400583z     Document Type: Article

References (56)

1. Thayer, A. M. Chem. Eng. News 2010, 13, 88
2. Babu, N. J.; Nangia, A. Cryst. Growth Des. 2011, 11, 2662-2679
3. Berge, S. M.; Bighley, L. D.; Monkhouse, D. C. J. Pharm. Sci. 1977, 66, 1
4. Serajuddin, A. T. M. Adv. Drug Delivery Rev. 2007, 59, 603-616
5. Banerjee, R.; Bhatt, P. M.; Ravindra, N. V.; Desiraju, G. R. Cryst. Growth Des. 2005, 5, 2299-2309
6. Thakuria, R.; Nangia, A. CrystEngComm 2011, 13, 1759-1764
7. Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896
8. Cherukuvada, S.; Babu, N. J.; Nangia, A. J. Pharm. Sci. 2011, 100, 3233-3244
9. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2009, 5 (3) 1013-1021
10. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzmán, H. R.; Almarsson, Ö. J. Am. Chem. Soc. 2003, 125, 8456-8457
11. Sanphui, P.; Goud, N. R.; Khandavilli, U. B. R.; Nangia, A. Cryst. Growth Des. 2011, 11, 4135-4145
12. Sanphui, P.; Goud, N. R.; Khandavilli, U. B. R.; Bhanoth, S.; Nangia, A. Chem. Commun. 2011, 47, 5013-5015
13. Banerjee, R.; Bhatt, P. M.; Ravindra, N. V.; Desiraju, G. R. Cryst. Growth Des. 2005, 5 (6) 2299-2309
14. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid-State Chemistry of Drugs, 2 nd ed.; West Lafayette: SSCI, Inc., 1999.
15. Good, D. J.; Rodríguez-Hornedo, N. Cryst. Growth Des. 2009, 9 (5) 2252-2264
16. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; Park, A. Pharm. Res. 2006, 23 (8) 1888-1897
17. Basavoju, S.; Boström, D.; Velaga, S. P. Cryst. Growth Des. 2006, 6 (12) 2699-2708
18. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499-516
19. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301-309
20. Yu, K. H. Recent Pat. Inflamm Allergy Drug Discovery 2007, 1, 69-75
21. Yamamoto, T.; Moriwaki, Y.; Fujimura, Y.; Takahashi, S.; Tsutsumi, Z.; Tsutsui, T.; Higashino, K.; Hada, T. Pharmacology 2000, 60, 34-40
22. Okamoto, K.; Eger, B. T.; Nishino, T.; Kondo, S.; Pai, E. F.; Nishino, T. J. Biol. Chem. 2003, 278, 1848-1855
23. Piran, M.; Metsger, L. US 2010/0317702 A1.
24. Koichi, M.; Kenzo, W.; Toshiyuki, H.; Mitsutaka, K. EP 1020454 B1.
25. Zhou, X.; Tang, X.; Deng, J.; Ye, W.; Luo, J.; Zhang, D.; Fan, B. WO 2008/067773 A1.
26. Dwivedi, S. D.; Prasad, A.; Roy, R. U.; Patel, M. R. WO 2011/101867 A2.
27. Khosravan, R.; Gabowski, B.; Wu, J. T.; Joseph-Ridge, N.; Vernillet, L. Br. J. Clin. Pharmacol. 2007, 65, 355-363
28. US-FDA GRAS chemical list, http://www.fda.gov/Food/ IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm091048.htm (accessed on April 8, 2013).
29. Zhu, X.; Wang, Y.; Lu, T. Acta Crystallogr. 2009, E65, o2603
30. Jiang, Q.-Y.; Qian, J.-J.; Gu, J.-M.; Tang, G.-P.; Hu, X.-R. Acta Crystallogr. 2011, E67, o1232
31. Thaimattam, R.; Dash, P. K.; Prasad, R.; Dhar, S. WO 2011/080651 A2.
32. Tombari, D. G.; Mangone, C. P.; Garcia, M. B.; Vecchioli, A.; Labriola, R. A. WO 2012/048861 A1.
33. Zhang, D.; Yan, W.; Li, R.; Dong, P.; Hu, Y. CN 101648926 A, 2010.
34. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126
35. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573
36. Walsh, R. D. B.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 2, 186-187
37. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327
38. Allen, F. H.; W. D. S. Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New J. Chem. 1999, 23, 25-34
39. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 7 th ed.; John Wiley: New York, 2005.
40. Smith, E.; Dent, G. Modern Raman Spectroscopy, A Practical Approach; John Wiley: New York, 2005.
41. Kaushik, P.; Thaimattam, R.; Prasad, M. WO 2012/098501 A1.
42. Schultheiss, N.; Newman, A. Cryst. Growth Des. 2009, 9, 2950-2967
43. Aakeröy, C. B; Forbes, S.; Desper, J. J. Am. Chem. Soc. 2009, 131, 17048-17049
44. Tumanov, N. A.; Myz, S. A.; Shakhtshneider, T. P.; Boldyreva, E. V. CrystEngComm 2012, 14, 305-313
45. Pak, C. Y. C.; Walters, O.; Arnold, L.; Holt, K.; Cox, C.; Barilla, D. J. Clin. Investigation 1977, 59, 426-431
46. So, A. Arthiritis Res. Ther. 2008, 10, 221 10.1186/ar2509
47. Newman, A. W.; Childs, S. L.; Cowans, B. A. Salt Cocrystal Form Selection, In Preclinical Development Handbook; John-Wiley, Hoboken, 2008; pp 455-481.
48. CrysAlis CCD and CrysAlis RED, Ver. 1.171.33.55; Oxford Diffraction Ltd: Yarnton, Oxfordshire, UK, 2008.
49. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A complete structure solution, refinement and analysis program J. Appl. Crystallogr. 2009, 42, 339-341
50. SAINT-Plus, version 6.45; Bruker AXS Inc.: Madison, Wisconsin, U.S.A., 2003.
51. SADABS, Program for Empirical Absorption Correction of Area Detector Data; Sheldrick, G. M. University of Göttingen: Göttingen, Germany, 1997.
52. SMART, version 5.625 and SHELX-TL, version 6.12; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.
53. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
54. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, Netherlands, 2002.
55. Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-Ray, Program for Better Quality of Crystallographic Figures; University of Missouri-Columbia, Missouri, 1999.
56. Powder Cell, A Program for Structure Visualization, Powder Pattern Calculation and Profile Fitting, http://www.ccp14.ac.uk/index.html (accessed on April 8, 2013). Pharmaceutical Cocrystals