Physicochemical Properties of Pharmaceutical Co-Crystals: A Case Study of Ten AMG 517 Co-Crystals
Source abstract
Abstract
The pharmaceutical co-crystal approach has been introduced recently to address poor physicochemical properties of new chemical entities. In this study we prepared and investigated ten co-crystals of AMG 517. Based on thermal analysis, 1 H NMR and p K a values we have prepared co-crystals rather than solvates or salts. We explored co-crystal physicochemical properties such as particle size, solubility, stability, hygroscopicity, and thermal properties as well as hydrogen bonding networks. We found that all co-crystals, for which we obtained single crystal structure, had the same two hydrogen bonds between the compound and the co-crystal former. In addition, we found good correlation between the melting point of the co-crystal former and the co-crystal but less correlation between the melting point and solubility of the co-crystals. In conclusion, within this series of co-crystals some design is possible by considering features of the compound and the co-crystal former.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Crystallization and Solubility Studies · Crystallography and molecular interactions · Chemical Thermodynamics and Molecular Structure
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Pharmaceutics, Amgen Inc., Cambridge, Massachusetts 02139
References (44)
Show source-provided references
1. FDA Challenges and Opportunity on the Critical Path to New Medical Products.http://www.fda.gov/oc/initiatives/criticalpath/whitepaper.html#innovation.
2. Tankosic T. · Drug Market Dev. · 2003 · 340
3. Lipinski C. · Am. Pharm. Rev. · 2002 · 5 · 82
4. Lipinski C. A. · Adv. Drug Delivery Rev. · 2001 · 46 · 310.1016/S0169-409X(00)00129-0 ↗
5. Kola I. · Nat. Rev. Drug Discovery · 2004 · 3 · 71110.1038/nrd1470 ↗
6. Prentis R. A. · Br. J. Clin. Pharmacol. · 1988 · 25 · 38710.1111/j.1365-2125.1988.tb03318.x ↗
7. Garad S. D. · Am. Pharm. Rev. · 2004 · 7 · 80
8. Neervannan S. · Am. Pharm. Rev. · 2004 · 7 · 108
9. Almarsson Ö. · Chem. Commun. · 2004 · 17 · 188910.1039/b402150a ↗
10. Aakeroy C. B. · Mol. Pharm. · 2007 · 4 · 31710.1021/mp060126o ↗
11. Childs S. L. · J. Am. Chem. Soc. · 2004 · 126 · 1333510.1021/ja048114o ↗
12. Childs S. L. · Mol. Pharm. · 2007 · 4 · 32310.1021/mp0601345 ↗
13. Desiraju G. R. · CrystEngComm · 2003 · 5 · 46610.1039/b313552g ↗
14. Dunitz J. D. · CrystEngComm · 2003 · 5 · 50610.1039/b315687g ↗
15. McNamara D. P. · Pharm. Res. · 2006 · 23 · 188810.1007/s11095-006-9032-3 ↗
16. Vishweshwar P. · J. Pharm. Sci. · 2006 · 95 · 49910.1002/jps.20578 ↗
17. Cooke M. W. · Am. Pharm. Rev. · 2007 · 10 · 54
18. Bailey Walsh R. D. · Chem. Commun. · 2003 · 186
19. Remenar J. F. · J. Am. Chem. Soc. · 2003 · 125 · 845610.1021/ja035776p ↗
20. Bak A. · J. Pharm. Sci. · 2007
21. Chen A. M. · Chem. Commun. · 2007 · 41910.1039/B612353H ↗
22. Variankaval N. · Cryst. Growth Des. · 2006 · 6 · 69010.1021/cg050462u ↗
23. Julius D. · Nature · 2001 · 413 · 20310.1038/35093019 ↗
24. Gavva N. R. · J. Pharmacol. Exp. Ther. · 2007 · 323 · 12810.1124/jpet.107.125674 ↗
25. FDA Select Committee on GRAS Substances (SCOGS) Database Overview.http://www.cfsan.fda.gov∼dms/opascogs.html/.
26. Stahl P. H. · 2002
27. Doherty E. M. · J. Med. Chem. · 2007 · 50 · 351510.1021/jm070190p ↗
28. ACD Advanced Chemistry Development Software Solaris V. 4.67,1994−2005
29. Aakeroy C. B. · Cryst. Growth Des. · 2006 · 6 · 47410.1021/cg050391z ↗
30. Jain A. · J. Pharm. Sci. · 2006 · 95 · 256210.1002/jps.20634 ↗
31. Levine, D. M.; Berenson, M. L.; Stephan, D.InStatistics for Managers, 2nd ed.Levine, D. M.; Berenson, M. L.; Stephan, D.Eds.Prentice Hall:Upper Saddle River, NJ, 1999; Chapter 13.3, pp783−794
32. Martin A. · J. Pharm. Sci. · 1980 · 69 · 48710.1002/jps.2600690503 ↗
33. Jain N. · J. Pharm. Sci. · 2001 · 90 · 23410.1002/1520-6017(200102)90:2<234::AID-JPS14>3.0.CO;2-V ↗
34. Ran Y. · J. Chem. Inf. Comput. Sci. · 2001 · 41 · 120810.1021/ci010287z ↗
35. Walden V. P. · Z. Elektrochem. · 1908 · 43 · 71310.1002/bbpc.19080144302 ↗
36. Dressman J. B. · Pharm. Res. · 1998 · 15 · 1110.1023/A:1011984216775 ↗
37. Yanez, E.; Daurio, D.; Buntich, S.; Bak, A.Physicochemical, solid-state, and pharmacokinetic properties of AMG 517 free base. Personal correspondence.
38. Yanez E. · 2007
39. Gilbert A. S. · Thermochim. Acta · 1999 · 339 · 13110.1016/S0040-6031(99)00301-9 ↗
40. Gilbert A. S. · Thermochim. Acta · 2005 · 428 · 110.1016/j.tca.2004.09.015 ↗
41. Stephenson G. A. · J. Pharm. Sci. · 1998 · 87 · 53610.1021/js970449z ↗
42. Sawamototo T. · J. Pharm. Pharmacol. · 1997 · 49 · 45010.1111/j.2042-7158.1997.tb06823.x ↗
43. 1999
44. Newman A. W. · J. Pharm. Sci. · 2008 · 97 · 104710.1002/jps.21033 ↗