Virtual screening identifies new cocrystals of nalidixic acid

Crystal Growth and Design

Volumn 14, Issue 4, 2014, Pages 1749-1755

  Grecu, Tudor ^a   Adams, Harry ^a   Hunter, Christopher A ^a   McCabe, James F ^b   Portell, Anna ^c   Prohens, Rafel ^c  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROSCOPY; X RAY POWDER DIFFRACTION;

3 ,4-DIHYDROXYBENZOIC ACIDS; ACTIVE PHARMACEUTICAL INGREDIENTS; COMPUTATIONAL FILTER; GROUP INTERACTION; PURE COMPONENTS; STRUCTURAL CHARACTERIZATION; VIRTUAL SCREENING; X RAY CRYSTAL STRUCTURES;

FUNCTIONAL GROUPS;

EID: 84897552535     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg401889h     Document Type: Article

References (48)

1. Morissette, S. L.; Almarsson, 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
2. Blagden, N.; De Matas, M.; Gavan, P.; York, P. Adv. Drug Delivery Rev. 2007, 59, 617-630
3. Smith, A. J.; Kavuru, P.; Wojtas, L.; Zaworotko, M. J.; Shytle, R. D. Mol. Pharm. 2011, 8, 1867-1876
4. Cherukuvada, S.; Babu, N. J.; Nangia, A. J. Pharm. Sci. 2011, 100, 3233-3244
5. Trask, A. V.; Motherwell, W.; Jones, W. Int. J. Pharm. 2006, 320, 114-123
6. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301-309
7. Hickey, M. B.; Almarsson, ö.; Peterson, M. L. CrystEngComm 2012, 14, 2349-2349
8. Galek, P. T. A.; Pidcock, E.; Wood, P. A.; Bruno, I. J.; Groom, C. R. CrystEngComm 2012, 14, 2391-2403
9. Almarsson, ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896
10. Shan, N.; Zaworotko, M. J. Drug Discovery Today 2008, 13, 440-446
11. FDA. Regulatory Classification of Pharmaceutical Co-Crystals. http://www.fda.gov/downloads/Drugs/Guidances/UCM281764.pdf (accessed August 2013).
12. Vishweshwar, P.; Mcmahon, J. A.; Bis, J. A.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499-516
13. Childs, S. L.; Wood, P. A.; Rodríguez-Hornedo, N. r.; Reddy, L. S.; Hardcastle, K. I. Cryst. Growth Des. 2009, 9, 1869-1888
14. Fábián, L. s. Cryst. Growth Des. 2009, 9, 1436-1443
15. Allen, F. H. Acta Crystallogr. Sect. B-Struct. Sci. 2002, 58, 380-388
16. Price, S. L. Acc. Chem. Res. 2008, 42, 117-126
17. Issa, N.; Karamertzanis, P. G.; Welch, G. W.; Price, S. L. Cryst. Growth Des. 2008, 9, 442-453
18. Karamertzanis, P. G.; Kazantsev, A. V.; Issa, N.; Welch, G. W.; Adjiman, C. S.; Pantelides, C. C.; Price, S. L. J. Chem. Theory Comput. 2009, 5, 1432-1448
19. Chan, H. S.; Kendrick, J.; Neumann, M. A.; Leusen, F. J. CrystEngComm 2013, 15, 3799-3807
20. Day, G. M.; Cooper, T. G.; Cruz-Cabeza, A. J.; Hejczyk, K. E.; Ammon, H. L.; Boerrigter, S. X.; Tan, J. S.; Della Valle, R. G.; Venuti, E.; Jose, J. Acta Crystallogr. Sect. B-Struct. Sci. 2009, 65, 107-125
21. Bardwell, D. A.; Adjiman, C. S.; Arnautova, Y. A.; Bartashevich, E.; Boerrigter, S. X.; Braun, D. E.; Cruz-Cabeza, A. J.; Day, G. M.; Della Valle, R. G.; Desiraju, G. R. Acta Crystallogr. Sect. B-Struct. Sci. 2011, 67, 535-551
22. Issa, N.; Barnett, S. A.; Mohamed, S.; Braun, D. E.; Copley, R. C.; Tocher, D. A.; Price, S. L. CrystEngComm 2012, 14, 2454-2464
23. Abramov, Y. A.; Loschen, C.; Klamt, A. J. Pharm. Sci. 2012, 101, 3687-3697
24. Mohammad, M. A.; Alhalaweh, A.; Velaga, S. P. Int. J. Pharm. 2011, 407, 63-71
25. Musumeci, D.; Hunter, C. A.; Prohens, R.; Scuderi, S.; McCabe, J. F. Chem. Sci. 2011, 2, 883-890
26. Grecu, T.; Hunter, C. A.; McCabe, J.; Gardiner, E. J. Cryst. Growth Des. 2014, 14, 165-171
27. Hunter, C. A., Chem. Sci. 2013
28. Calero, C. S.; Farwer, J.; Gardiner, E. J.; Hunter, C. A.; Mackey, M.; Scuderi, S.; Thompson, S.; Vinter, J. G. Phys. Chem. Chem. Phys. 2013, 15, 18262-18273
29. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324
30. Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610
31. For an analysis that considers only pairing of the most polar sites, see the following: Aakeroy, C. B.; Desper, J.; Smith, M. M. Chem. Commun. 2007, 3936-3938
32. Cresset torchV10lite. http://www.cresset-group.com/products/torch/ torchlite/.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
34. Sheldrick, G. M. Acta Crystallogr., Sect. A 2007, 64, 112-122
35. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
36. Boultif, A.; Louër, D. J. Appl. Crystallogr. 2004, 37, 724-731
37. Rodríguez-Carvajal, J. Phys. B: Condens. Matter 1993, 192, 55-69
38. Spartan; Wavefunction Inc.: Irvine, CA.
39. O'Boyle, N. M.; Banck, M.; James, C. A.; Morley, C.; Vandermeersch, T.; Hutchison, G. R. J. Cheminf. 2011, 3, 1-14
40. Favre-Nicolin, V.; Cerny, R. J. Appl. Crystallogr. 2002, 35, 734-743
41. http://www.ecfr.gov/cgi-bin/text-idx?c=ecfr&SID= 4f70083a7e458a879baeaf15975a0166&rgn=div5&view=text&node=21:3.0.1.1. 14&idno=21#21:3.0.1.1.14.2.1.2
42. http://www.fda.gov/Food/IngredientsPackagingLabeling/ FoodAdditivesIngredients/ucm091048.htm.
43. Everything Added to Food in the United States. http://www.biobased.us/ eafus.pdf.
44. Gangavaram, S.; Raghavender, S.; Sanphui, P.; Pal, S.; Manjunatha, S. G.; Nambiar, S.; Nangia, A. Cryst. Growth Des. 2012, 12, 4963-4971
45. Friščić, T.; Trask, A. V.; Jones, W.; Motherwell, W. Angew. Chem. 2006, 118, 7708-7712
46. Friščić, T.; Childs, S. L.; Rizvi, S. A.; Jones, W. CrystEngComm 2009, 11, 418-426
47. Stahly, G. P. Cryst. Growth Des. 2007, 7, 1007-1026
48. Schultheiss, N.; Newman, A. Cryst. Growth Des. 2009, 9, 2950-2967