Formation of isomorphic desolvates: Creating a molecular vacuum

Journal of Pharmaceutical Sciences

Volumn 87, Issue 5, 1998, Pages 536-542

  Stephenson, Gregory A ^a   Groleau, Edward G ^a   Kleemann, Rita L ^a   Xu, Wei ^b,c   Rigsbee, Daniel R ^a  

^a ELI LILLY AND COMPANY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CEFACLOR; CEFALEXIN; ERYTHROMYCIN; SPIRAPRIL;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG CONFORMATION; DRUG DELIVERY SYSTEM; HYDROGEN BOND; MICROCALORIMETRY; MOLECULAR MODEL; SOLVATION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; WETTABILITY; X RAY CRYSTALLOGRAPHY;

EID: 0031958398     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970449z     Document Type: Article

References (28)

1. Pfeiffer, R. R.; Yang, K. S.; and Tucker, M. A. Crystal Pseudopolymorphism of Cephaloglycin and Cephalexin J. Pharm. Sci. 1970, 59 (12), 1809-1812.
2. Byrn, S. R.; Lin, C. T.; Perrier, P.; Clay, G. G.; and Sutton, P. A. Solid State Photooxidation of 21-cortisol tert-butylacetate to 21-cortisone. J. Org. Chem. 1982, 47, 2978-81.
3. Otsuka, M.; Kaneniwa, N. Hygroscopicity of Cephalexin. Yakugaku Zasshi 1982, 102 (4), 359-364.
4. Bauer, J.; Quick, J.; Oheim, R. Alternate Interpretation of the Role of Water in the Erythromycin Structure. J. Pharm. Sci. 1985, 74, 899-90s0.
5. Kitiagorodski, A. I. Molecular Crystals and Molecules; Volume 29 of Physical Chemistry A series of monographs; Loebl, E. M., Ed.; Academic Press: New York, 1973.
6. Gavezzotti, A.; Filippini, G. Polymorphic forms of Organic Crystals at Room Conditions: Thermodynamic and Structural Implications. J. Am. Chem. Soc. 1995, 117, 12299-12305.
7. Gavezzotti, A. Calculations on Packing Energies, Packing Efficiencies and Rotational Freedom for Molecular Crystals. Nouv. J. Chim. 1982, 6, 444-450.
8. Burger A.; Ramberger, R. On the Polymorphism of Pharmaceuticals and other Molecular Crystals I. Theory of Thermodynamic Rules. Mikorchim. Acta [Wein] 1979, II, 259-271.
9. Griesser, U. J.; Burger, A.; Mereiter, K. The Polymorphic Drug Substances of the European Pharmacopoeia. Part 9. Physicochemical Properties and Crystal Structures of Acetazolamide Crystal Forms. J. Pharm. Sci. 1997, 86, 352-358.
10. The program Cerius 2 was developed by BIOSYM/Molecular Simulations.
11. Connolly, M. L. Analytical Molecular Surface Calculation. J. Appl. Crystal. 1983, 16, 548-558.
12. Threlfall, T. L. Analysis of Organic Polymorphs, A Review. Analyst 1995, 120, 2437-2460. Note: In the present study we refer to nonstoichiometric solvates of variable solvent content.
13. Nonstoichiometric desolvates need not always be of variable composition. The site symmetry of the solvent molecule in the crystal lattice dictates that it is a nonstoichiometric solvate; e.g., the solvent molecule may occupy a crystallographic special position.
14. (a) Bergen, M. S. Dynamic moisture sorption gravimetry (DMSG) and solid-state stability. Land-O-Lakes Conference, Madison, WI, 1994.
15. (b) Cox, J. S. G.; Woodard, G. D.; McCrone, W. C. Solid-State Chemistry of Cromolyn Sodium (disodium cromoglycate). J. Pharm. Sci. 1971, 60 (10), 1458-1465.
16. Stephenson, G. A.; Stowell, J. G.; Pfeiffer, R. R., Toma, P. H.; Byrn, S. R. Solid-State Investigations of Erythromycin A Dihydrate: Structure, NMR Spectroscopy, and Hygroscopicity. J. Pharm. Sci. 1997, 86, 1239-1244.
17. Xu, W.; Wahle, M.; Stowell, J. G.; Byrn, S. R. Spirapril Hydrochloride Hydrate. Acta Crystallogr C In press.
18. Byrn, S. R. Solid State Chemistry of Drugs; Academic Press: New York, 1982.
19. Pfeiffer, R. R.; Tucker, M. A. Crystalline Cephalexin Monohydrate. U. S. patent 1277137, 1970.
20. Ahlneck, C.; Zografi, G. The Molecular Basis of the Effects of Moisture on the Physical and Chemical Stability of Drugs in the Solid-State. Int. J. Pharm. 1990, 62, 87-95.
21. Kitamura, S.; Koda, S.; Miyamae, A.; Yasuda, T.; Morimoto, Y Int. J. Pharm. 1990, 59, 217-224.
22. Byrn, S. R.; and Kessler, D. W. The Solid State Reactivity of the Crystal Forms of Hydrocortisone Esters. Tetrahedron 1987, 43 (7), 1335-1343.
23. Pikal, M. Personal communication.
24. Although a general shift toward smaller d spacing for most reflections is observed, this is not an absolute requirement. It is possible for a unit cell parameter to expand upon desolvation if the other parameters shrink sufficiently to cause a net reduction in the overall unit cell volume.
25. Copet, C.; Rigsbee, D. R.; Pikal, M. J. The Study of Enthalpy Relaxation in Glassy Pharmaceuticals with Isothermal Calorimetry. Pharm. Res. 1997, 14 (11), S186.
26. Hansen, L. D.; Lewis, E. A.; Eatough, D. J.; Bergstrom, R. G.; DeGraft-Johnson, D. Kinetics of Drug Decomposition by Heat Conduction Calorimetry. Pharm. Res. 1989, 6 (1), 20-27.
27. The difference in packing efficiency was determined as the difference in the packing coefficient for the solvate minus the desolvate divided by the packing coefficient of the solvate.
28. Xu, W. Investigations of Solid-State Stability of Selected Bioactive Compounds. Ph.D. Thesis, Purdue University, August 1997.