The predictably elusive form II of aspirin

Journal of the American Chemical Society

Volumn 127, Issue 48, 2005, Pages 16802-16803

  Vishweshwar, Peddy ^a   McMahon, Jennifer A ^a   Oliveira, Mark ^b   Peterson, Matthew L ^b   Zaworotko, Michael J ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b TransForm Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; CARBAMAZEPINE;

ARTICLE; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG STRUCTURE; HYDROGEN BOND; PHYSICAL CHEMISTRY; PREDICTION; STRUCTURE ANALYSIS; X RAY POWDER DIFFRACTION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ASPIRIN; CRYSTALLIZATION; MODELS, MOLECULAR; X-RAY DIFFRACTION;

EID: 28844471349     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056455b     Document Type: Article

References (48)

1. (a) Bernstein, J. Polymorphism in Molecular Crystals; Clarendon: Oxford, 2002.
2. (b) Davey, R. J. Chem. Commun. 2003, 1463.
3. (c) Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193.
4. (a) Kuhnert-Brandstätter, M.; Aepkers, M. Mikroskopie 1961, 16, 189.
5. (b) Davey, R. J.; Blagden, N.; Potts, G. D.; Docherty, R. J. Am. Chem. Soc. 1997, 119, 1767.
6. (c) He, X.; Stowell, J. G.; Morris, K. R.; Pfeiffer, R. R.; Li, H.; Stahly, G. P.; Byrn, S. R. Cryst. Growth Des. 2001, 1, 305.
7. (d) Weissbuch, I.; Lahav, M.; Leiserowitz, L. Cryst. Growth Des. 2003, 3, 125.
8. (e) Rubin-Preminger, J. M.; Bernstein, J. Cryst. Growth Des. 2005, 5, 1343.
9. Haleblian, J. K. J. Pharm. Sci. 1975, 64, 1269.
10. (a) Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889.
11. (b) Fleischman, S. G.; Kuduva, S. S.; McMahon, J. A.; Moulton, B.; Walsh, R. D. B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Cryst. Growth Des. 2003, 3, 909.
12. (c) 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.
13. (d) Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 1013.
14. LaFont, O. Rev. d'histoire de la pharmacie 1996, 43, 269.
15. (a) Aspirin and Other Salicylates; Vane, J. R., Bottling, R. M., Eds.; Chapman and Hall: London, 1992.
16. (b) Moore, N.; Van Ganse, E.; Le Parc, J. M.; Wall, R.; Schneid, H.; Farhan, M.; Verrière, F.; Pelen, F. The PAIN Study: Paracetamol, Aspirin and Ibuprofen. Clin. Drug Invest. 1999, 18, 89.
17. (c) Mehta, A. Chem. Eng. News 2005, June, 46-47.
18. (d) More information on aspirin can be found in Bayer's aspirin web site at URL http://www.aspirin.de.
19. (a) Mitchell, A. G.; Saville, D. J. J. Pharm. Pharmacol. 1967, 19, 729.
20. (b) Tawashi, R. Science 1968, 160, 76.
21. (c) Tawashi, R. J. Pharm. Pharmacol. Lett. 1969, 21, 701.
22. (d) Mitchell, A. G.; Saville, D. J. J. Pharmacol. 1969, 21, 28.
23. (e) de Bisschop, M. J. Pharm. Belg. 1970, 25, 330.
24. (f) Summers, M. P.; Carless, J. E.; Enever, R. P. J. Pharm. Pharmacol. Lett. 1970, 22, 615.
25. (g) Kildsig, D. O.; Denbo, R.; Peck, G. E. J. Pharm. Pharmacol. 1971, 23, 374.
26. (h) Bauer, K.; Voege, H. Pharm. Ind. 1972, 34, 960.
27. (i) Summers, M. P.; Enever, R. P.; Carless, J. E. In Particle Growth in Suspensions; Smith, A. L., Ed.; Academic Press: London, 1973.
28. (j) Bettinetti, G. P.; Giordano, F.; Giuseppetti, G. Farmaco, Ed. Pratica 1975, 30, 244.
29. (k) Agafonov, V. N.; Leonidov, N. B. Khimiko-Farmat. Zhurnal 1978, 12, 127.
30. (l) Jerslev, B.; Lund, U. R. Dan. Sch. Pharm. 1981, 9, 61.
31. Chang, C. J.; Diaz, L. E.; Morin, F.; Grant, D. M. R. Dan. Sch. Pharm. 1986, 24, 768.
32. (a) Pfeiffer, R. R. J. Pharm. Pharmacol. Lett. 1971, 23, 75.
33. (b) Mitchell, A. G.; Milaire, B. L.; Saville, D. J.; Griffiths, R. V. J. Pharm. Pharmacol 1971, 23, 534.
34. (c) Mulley, B. A.; Rye, R. M.; Shaw, P. J. Pharm. Pharmacol. 1971, 23, 902.
35. (d) Schwartzman, G. J. Pharm. Pharmacol. Lett. 1972, 24, 169.
36. (a) Ouvrard, C.; Price, S. L. Cryst. Growth Des. 2004, 4, 1119.
37. (b) Glaser, R. J. Org. Chem. 2001, 66, 771.
38. (c) Payne, R. S.; Rowe, R. C.; Roberts, R. J.; Charlton, M. H.; Docherty, R. J. Comput. Chem. 1999, 20, 262.
39. (a) Wheatley, P. J. J. Chem. Soc. 1964, 6036.
40. (b) Kim, Y.; Machida, K.; Taga, T.; Osaki, K. Chem. Pharm. Bull. 1985, 33, 2641.
41. Wilson, C. C. New J. Chem. 2002, 26, 1733.
42. Desiraju G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
43. obs = 0.308. Crystal size: 0.25 × 0.15 × 0.005 mm. All atoms were refined isotropically because of the relatively weak data.
44. (a) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629.
45. (b) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
46. (c) Frankenbach, G. M.; Etter, M. C. Chem. Mater. 1992, 4, 272.
47. Leiserowitz, L.; Nader, F. Acta Crystallogr. 1977, B33, 2719.
48. obs = 0.119. The co-crystal can also be obtained by solvent-drop grinding of equimolar amounts of aspirin and carbamazepine (20 μL of ethyl acetate per 100 mg of solid, 2-4 min of grinding).