4-aminosalicylic acid adducts

Crystal Growth and Design

Volumn 13, Issue 4, 2013, Pages 1551-1557

  Cherukuvada, Suryanarayan ^a   Bolla, Geetha ^a   Sikligar, Kanishka ^a,b   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b Bhaskar Pharmacy College   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4-AMINOSALICYLIC ACIDS; ACTIVE PHARMACEUTICAL INGREDIENTS; ANTITUBERCULOSIS; CO-CRYSTAL FORMATION; CO-CRYSTALS; PHENOL GROUPS; POWDER X RAY DIFFRACTION; X RAY CRYSTAL STRUCTURES;

CRYSTAL STRUCTURE; HYDRATES; HYDRATION; HYDROGEN BONDS; SALTS; X RAY DIFFRACTION;

SODIUM SULFATE;

EID: 84875802425     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg301798s     Document Type: Article

References (61)

1. Elsevier. para -Aminosalicylic Acid Monograph Tuberculosis 2008, 88, 137
2. Gutierrez-Lugo, M. -T.; Bewley, C. A. J. Med. Chem. 2008, 51, 2606
3. WHO. Model Listof Essential Medicines. http://www.who.int/selection- medicines/committees/expert/17/sixteenth-adult-list-en.pdf.
4. O'Donnell, L. J. D.; Arvind, A. S.; Hoang, P.; Cameron, D.; Talbot, I. C.; Jewell, D. P.; Lennard-Jones, J. E.; Farthing, M. J. G. Gut 1992, 33, 947
5. Schreiber, S.; Howaldt, S.; Raedler, A. Gut 1993, 34, 1081
6. Sandborn, W. J.; Feagan, B. G.; Lichtenstein, G. R. Aliment. Pharmacol. Ther. 2007, 26, 987
7. Cambridge Structural Database, ver. 5.33, ConQuest 1.14, November 2011 release, August 2012, update; www.ccdc.cam.ac.uk.
8. 4-ASA CSD refocde AMSALA01: Lin, C.-T; Siew, P. Y.; Byrn, S. R. J. Chem. Soc., Perkin Trans. 2 1978, 957
9. 5-ASA CSD refcode SAQJAV: Banic-Tomisic, Z.; Kojic-Prodic, B.; Sirola, I. J. Mol. Struct. 1997, 416, 209
10. Rekker, R. F.; Nauta, W. T. J. Med. Pharm. Chem. 1960, 2, 281
11. Wesalowski, M. Thermochim. Acta 1977, 21, 243
12. Rotich, M. K.; Glass, B. D.; Brown, M. E. J. Therm. Anal. Calorim. 2001, 64, 681
13. Chakraborty, S.; Gruber, T.; Barry, C. E., III; Boshoff, H. I.; Rhee, K. Y. Science 2013, 339, 88
14. Grobelny, P.; Mukherjee, A.; Desiraju, G. R. CrystEngComm 2011, 13, 4358
15. Caira, M. R. J. Crystallogr. Spectrosc. Res. 1992, 22, 193
16. Centolella, A. P. US Patent 2,844,625, 1958.
17. Forbes, R. T.; York, P.; Davidson, J. R. Int. J. Pharm. 1995, 126, 199
18. Braga, D.; Maini, L.; de Sanctis, G.; Rubini, K.; Grepioni, F.; Chierotti, M. R.; Gobetto, R. Chem.-Eur. J. 2003, 9, 5538
19. Sarma, B.; Nath, N. K.; Bhogala, B. R.; Nangia, A. Cryst. Growth Des. 2009, 9, 1546
20. Black, S. N.; Collier, E. A.; Davey, R. J.; Roberts, R. J. J. Pharm. Sci. 2007, 96, 1053
21. André, V.; Braga, D.; Grepioni, F.; Duarte, M. T. Cryst. Growth Des. 2009, 9, 5108
22. André, V.; Duarte, M. T.; Braga, D.; Grepioni, F. Cryst. Growth Des. 2012, 12, 3082
23. Qiu, Y.; Chen, Y.; Zhang, G. G. Z., Eds. Developing Solid Oral Dosage Forms. Pharmaceutical Theory and Practice; Academic Press: New York, 2009. The word adduct (mentioned on pp 25-27 of this book) encompasses all multicomponent systems whether ionic (salt), molecular (cocrystal), or ionic/molecular (salt cocrystal, salt solvate, cocrystal solvate, etc.) in nature.
24. Childs, S. L.; Stahly, G. P.; Park, A. Mol. Pharmaceutics 2007, 4, 323
25. Bhogala, B. R.; Basavoju, S.; Nangia, A. CrystEngComm 2005, 7, 551
26. Cruz-Cabeza, A. J. CrystEngComm 2012, 14, 6362
27. Bhogala, B. R.; Nangia, A. Cryst. Growth Des. 2003, 3, 547
28. Aakeroy, C. B.; Fasulo, M. E.; Desper, J. Mol. Pharmaceutics 2007, 4, 317
29. Hathwar, V. R.; Pal, R.; Guru Row, T. N. Cryst. Growth Des. 2010, 10, 3306
30. Aitipamula, S.; Banerjee, R.; Bansal, A. K.; Biradha, K.; Cheney, M. L.; Choudhury, A. R.; Desiraju, G. R.; Dikundwar, A. G.; Dubey, R.; Duggirala, N.; Ghogale, P. P.; Ghosh, S.; Goswami, P. K.; Goud, N. R.; Jetti, R. K. R.; Karpinski, P.; Kaushik, P.; Kumar, D.; Kumar, V.; Moulton, B.; Mukherjee, A.; Mukherjee, G.; Myerson, A. S.; Puri, V.; Ramanan, A.; Rajamannar, T.; Reddy, C. M.; Rodriguez-Hornedo, N.; Rogers, R. D.; Row, T. N. G.; Sanphui, P.; Shan, N.; Shete, G.; Singh, A.; Sun, C. C.; Swift, J. A.; Thaimattam, R.; Thakur, T. S.; Thaper, R. K.; Thomas, S. P.; Tothadi, S.; Vangala, V. R.; Vishweshwar, P.; Weyna, D. R.; Zaworotko, M. J. Cryst. Growth Des. 2012, 12, 2147-4290 and references therein
31. Clarke, H. D.; Hickey, M. B.; Moulton, B.; Perman, J. A.; Peterson, M. L.; Wojtas, Ł.; Almarsson, Ö.; Zaworotko, M. J. Cryst. Growth Des. 2012, 12, 4194
32. Goswami, P. K.; Thaimattam, R.; Ramanan, A. Cryst. Growth Des. 2013, 13, 360
33. Nath, N. K.; Kumar, S. S.; Nangia, A. Cryst. Growth Des. 2011, 11, 4594
34. Nath, N. K.; Aggarwal, H.; Nangia, A. Cryst. Growth Des. 2011, 11, 967
35. Sarma, B.; Roy, S.; Nangia, A. Chem. Commun. 2006, 4918
36. Castro, R. A. E.; Maria, T. M. R.; évora, A. O. L.; Feiteira, J. C.; Silva, M. R.; Beja, A. M.; Canotilho, J.; Eusébio, M. E. S. Cryst. Growth Des. 2010, 10, 274
37. Atwood, J. L.; Barbour, L. J.; Jerga, A.; Schottel, B. L. Science 2002, 298, 1000
38. van Eijck, B. P.; Kroon, J. Acta Crystallogr. 2000, B56, 535
39. Ebenezer, S.; Muthiah, P. T. Cryst. Growth Des. 2012, 12, 3766
40. Stanley, N.; Sethuraman, V.; Muthiah, P. T.; Luger, P.; Weber, M. Cryst. Growth Des. 2002, 2, 631
41. Shan, N.; Bond, A. D.; Jones, W. Tetrahedron Lett. 2002, 43, 3101
42. Balasubramani, K.; Muthiah, P. T.; Lynch, D. E. Chem. Cent. J. 2007, 1, 28
43. Thakur, T. S.; Desiraju, G. R. Cryst. Growth Des. 2008, 8, 4031
44. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256
45. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem., Int. Ed. 1995, 34, 1555
46. Sridhar, B.; Nanubolu, J. B.; Ravikumar, K. CrystEngComm 2012, 14, 7065
47. Delori, A.; Friščić, T.; Jones, W. CrystEngComm 2012, 14, 2350
48. Trask, A. V.; Jones, W. Top. Curr. Chem. 2005, 254, 41
49. Shan, N.; Toda, F.; Jones, W. Chem. Commun. 2002, 2372
50. Verdolino, V.; Cammi, R.; Munk, B. H.; Schlegel, H. B. J. Phys. Chem. B 2008, 112, 16860
51. Stratford, M. R. L.; Dennis, M. F.; Hoskin, P.; Phillips, H.; Hodgkiss, R. J.; Rojas, A. Brit. J. Can. 1996, 74, 16
52. Bardwell, D. A.; Adjiman, C. S.; Arnautova, Y. A.; Bartashevich, E.; Boerrigter, S. X. M.; Braun, D. E.; Cruz-Cabeza, A. J.; Day, G. M.; Della Valle, R. G.; Desiraju, G. R.; van Eijck, B. P.; Facelli, J. C.; Ferraro, M. B.; Grillo, D.; Habgood, M.; Hofmann, D. W. M.; Hofmann, F.; Jose, K. V. J.; Karamertzanis, P. G.; Kazantsev, A. V.; Kendrick, J.; Kuleshova, L. N.; Leusen, F. J. J.; Maleev, A. V.; Misquitta, A. J.; Mohamed, S.; Needs, R. J.; Neumann, M. A.; Nikylov, D.; Orendt, A. M.; Pal, R.; Pantelides, C. C.; Pickard, C. J.; Price, L. S.; Price, S. L.; Scheraga, H. A.; van de Streek, J.; Thakur, T. S.; Tiwari, S.; Venuti, E.; Zhitkov, I. K. Acta Crystallogr. 2011, B67, 535
53. SAINT-Plus, version 6.45; Bruker AXS Inc.: Madison, Wisconsin, USA, 2003.
54. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1997.
55. SMART, version 5.625, and SHELX-TL, version 6.12; Bruker AXS Inc.: Madison, Wisconsin, 2000.
56. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
57. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, Netherlands, 2002.
58. CrysAlis CCD and CrysAlis RED, version 1.171.33.55; Oxford Diffraction Ltd: Oxfordshire, U.K., 2008.
59. Dolomanov, O. V.; Blake, A. J.; Champness, N. R.; Schröder, M. J. Appl. Crystallogr. 2003, 36, 1283
60. 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.
61. PowderCell. Program for Structure Visualization, Powder Pattern Calculation, and Profile Fitting. http://www.ccp14.ac.uk/index.html.