Applying thermodynamic and kinetic parameters to predict the physical stability of two differently prepared amorphous forms of simvastatin

Current Drug Delivery

Volumn 6, Issue 4, 2009, Pages 374-382

  Graeser, Kirsten A ^a,b   Patterson, James E ^b   Rades, Thomas ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Adam Gibbs; Amorphous; DSC; Kohlrausch Williams Watts; Physical stability; Simvastatin

Indexed keywords

SIMVASTATIN;

ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; DRUG STABILITY; ENERGY; ENTHALPY; ENTROPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; PRIORITY JOURNAL; SOLID; TECHNIQUE; THERMODYNAMICS; X RAY POWDER DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLIZATION; DRUG STABILITY; ENTROPY; SIMVASTATIN; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL; THERMODYNAMICS; X-RAY DIFFRACTION;

EID: 68949083240     PISSN: 15672018     EISSN: None     Source Type: Journal    
DOI: 10.2174/156720109789000492     Document Type: Article

References (44)

1. Hancock, B.C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci., 1997, 86, 1-12.
2. Shalaev, E.; Zografi, G. In: Amorphous Food and Pharmaceutical Systems, The Royal Society of Chemistry: Cambridge, 2002.
3. Petit, S.; Coquerel, G. In: Polymorphism, Hilfiker, R., Ed. Wiley- VCH: Weinheim, 2006, pp. 259-286.
4. Imaizumi, H. Stability and several physical properties of amorphous and crystalline forms of indomethacin. Chem. Pharm. Bull., 1980, 28, 2565-2569.
5. Behme, R.J.; Brooke, D. Heat of fusion measurement of a low melting polymorph of carbamazepine that undergoes multiplephase changes during differential scanning calorimetry. J. Pharm. Sci., 1991, 80, 986-990.
6. Egawa, H.; Maeda, S.; Yonemochi, E.; Oguchi, T.; Yamamoto, K.; Nakai, Y. Solubility parameter and dissolution behaviour of cefalexin powders with different crystallinity. Chem. Pharm. Bull., 1992, 40, 819-820.
7. Zhang, F.; Aaltonen, J.; Tian, F.; Saville, D.J.; Rades, T. Influence of particle size and preparation methods on the physical and chemical stability of amorphous simvastatin. Eur. J. Pharm. Biopharm., 2009, 71, 64-70.
8. Andronis, V.; Zografi, G. Crystal nucleation and growth of indomethacin polymorphs from the amorphous state. J. Non Cryst. Solids, 2000, 271, 236-248. (Pubitemid 30876406)
9. Ishida, H.; Wu, T.A.; Yu, L.A. Sudden rise of crystal growth rate of nifedipine near T-g without and with polyvinylpyrrolidone. J. Pharm. Sci., 2007, 96, 1131-1138.
10. Duddu, S.P.; DalMonte, P.R. Effect of glass transition temperature on the stability of lyophilized formulations containing a chimeric therapeutic monoclonal antibody. Pharm. Res., 1997, 14, 591-595. (Pubitemid 27220275)
11. Tang, X.L.C.; Pikal, M.J.; Taylor, L.S. A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers. Pharm. Res., 2002, 19, 477-483. (Pubitemid 34408948)
12. Andronis, V.; Yoshioka, M.; Zografi, G. Effects of sorbed water on the crystallization of indomethacin from the amorphous state. J. Pharm. Sci., 1997, 86, 346-351. (Pubitemid 27113770)
13. Crowley, K.J.; Zografi, G. The use of thermal methods for predicting glass-former fragility. Thermochim. Acta, 2001, 380, 79-93. (Pubitemid 33100002)
14. Qi, S.; Avalle, P.; Saklatvala, R.; Craig, D.Q.M. An investigation into the effects of thermal history on the crystallisation behaviour of amorphous paracetamol. Eur. J. Pharm. Biopharm., 2008, 69, 364-371.
15. Abdul-Fattah, A.M.; Dellerman, K.M.; Bogner, R.H.; Pikal, M.J. The effect of annealing on the stability of amorphous solids: Chemical stability of freeze-dried moxalactam. J. Pharm. Sci., 2007, 96, 1237-1250.
16. Zhou, D.L.; Zhang, G.G.Z.; Law, D.; Grant, D.J.W.; Schmitt, E.A. Physical stability of amorphous pharmaceuticals: Importance of configurational thermodynamic quantities and molecular mobility. J. Pharm. Sci., 2002, 91, 1863-1872.
17. Marsac, P.J.; Konno, H.; Taylor, L.S. A comparison of the physical stability of amorphous felodipine and nifedipine systems. Pharm. Res., 2006, 23, 2306-2316.
18. Gupta, P.; Chawla, G.; Bansal, A.K. Physical stability and solubility advantage from amorphous celecoxib: The role of thermodynamic quantities and molecular mobility. Mol. Pharm., 2004, 1, 406-413.
19. Aso, Y.; Yoshioka, S.; Kojima, S. Molecular mobility-based estimation of the crystallization rates of amorphous nifedipine and phenobarbital in poly(vinylpyrrolidone) solid dispersions. J. Pharm. Sci., 2004, 93, 384-391. (Pubitemid 38180444)
20. Hancock, B.C.; Shamblin, S.L.; Zografi, G. Molecular mobility of amorphous pharmaceutical solids below their glass-transition temperatures. Pharm. Res., 1995, 12, 799-806.
21. Vyazovkin, S.; Dranca, I. Physical stability and relaxation of amorphous indomethacin. J. Phys. Chem. B., 2005, 109, 18637-18644. (Pubitemid 41472062)
22. Richards, W.T. Remarks concerning the formation and crystallization of vitreous media. J. Chem. Phys., 1936, 4, 449-457.
23. Tombari, E.; Ferrari, C.; Johari, G.P.; Shanker, R.M. Calorimetric relaxation in pharmaceutical molecular glasses and its utility in understanding their stability against crystallization. J. Phys. Chem. B., 2008, 112, 10806-10814.
24. Kawakami, K.; Pikal, M.J. Calorimetric investigation of the structural relaxation of amorphous materials: Evaluating validity of the methodologies. J. Pharm. Sci., 2005, 94, 948-965.
25. Hancock, B.C.; Shamblin, S.L. Molecular mobility of amorphous pharmaceuticals determined using differential scanning calorimetry. Thermochim. Acta, 2001, 380, 95-107. (Pubitemid 33096427)
26. Mao, C.; Chamarthy, S.; Pinal, R. Time-dependence of molecular mobility during structural relaxation and its impact on organic amorphous solids: An investigation based on a calorimetric approach. Pharm. Res., 2006, 23, 1906-1917. (Pubitemid 44200555)
27. Shamblin, S.L.; Hancock, B.C.; Dupuis, Y.; Pikal, M.J. Interpretation of relaxation time constants for amorphous pharmaceutical systems. J. Pharm. Sci., 2000, 89, 417-427.
28. Mao, C.; Chamarthy, S.P.; Pinal, R. Calorimetric study and modeling of molecular mobility in amorphous organic pharmaceutical compounds using a modified Adam-Gibbs approach. J. Phys. Chem. B., 2007, 111, 13243-13252. (Pubitemid 350254031)
29. Gibbs, J.H.; Dimarzio, E.A. Nature of the Glass Transition and the Glassy State. J. Chem. Phys., 1958, 28, 373-383.
30. Adam, G.; Gibbs, J.H. On temperature dependence of cooperative relaxation properties in glass forming liquids. J. Chem. Phys., 1981, 43, 139-146.
31. Scherer, G.W. Use of the Adam-Gibbs Equation in the Analysis of Structural Relaxation. J. Am. Ceram. Soc., 1984, 67, 504-511. (Pubitemid 14602502)
32. Rault, J. Origin of the VTF law in glass forming materials: the a-βbifurcation. J. Non Cryst. Solids, 2000, 271, 177-217.
33. Graeser, K.A.; Patterson, J.E.; Zeitler, J.A.; Gordon, K.C.; Rades, T. Correlating thermodynamic and kinetic parameters with amorphous stability. Eur. J. Pharm. Sci., 2009, doi:10.1016/j.ejps. 2009.04.005.
34. Savolainen, M.; Heinz, A.; Strachan, C.; Yliruusi, J.; Rades, T.; Sandler, N. Screening for differences in the amorphous state of indomethacin using multivariate visualization. Eur. J. Pharm. Sci., 2007, 32, 113-123.
35. Yonemochi, E.; Inoue, Y.; Buckton, G.; Moffat, A.; Oguchi, T.; Yamamoto, K. Differences in crystallization behavior between quenched and ground amorphous ursodeoxycholic acid. Pharm. Res., 1999, 16, 835-840. (Pubitemid 29284193)
36. Patterson, J.E.; James, M.B.; Forster, A.H.; Lancaster, R.W.; Butler, J.M.; Rades, T. The influence of thermal and mechanical preparative techniques on the amorphous state of four poorly soluble compounds. J. Pharm. Sci., 2005, 94, 1998-2012. (Pubitemid 41551483)
37. Graeser, K.A.; Strachan, C.J.; Patterson, J.E.; Gordon, K.C.; Rades, T. Physicochemical properties and stability of two differently prepared amorphous forms of simvastatin. Cryst. Growth Des., 2008, 8, 128-135.
38. Hill, V.L.; Craig, D.Q.M.; Feely, L.C. The effects of experimental parameters and calibration on MTDSC data. Int. J. Pharm., 1999, 192, 21-32.
39. Putnam, R.L.; Boerio-Goates, J. Heat capacity measurements and thermodynamic functions of crystalline sucrose at temperatures from 5 K to 342 K. J. Chem. Thermodyn., 1993, 25, 607-613.
40. Luthra, S.A.; Hodge, I.M.; Pikal, M.J. Investigation of the impact of annealing on global molecular mobility in glasses: Optimization for stabilization of amorphous pharmaceuticals. J. Pharm. Sci., 1999, 97, 3865-3882.
41. Yu, L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv. Drug Deliv. Rev., 2001, 48, 27-42. (Pubitemid 32454482)
42. Shamblin, S.L.; Tang, X.L.; Chang, L.Q.; Hancock, B.C.; Pikal, M.J. Characterization of the time scales of molecular motion in pharmaceutically important glasses. J. Phys. Chem. B., 1999, 103, 4113-4121.
43. Fukuoka, E.; Makita, M.; Yamamura, S. Some physicochemical properties of glassy indomethacin. Chem. Pharm. Bull., 1986, 34, 4314-4321. (Pubitemid 17201167)
44. Lu, Q.; Zografi, G. Properties of citric acid at the glass transition. J. Pharm. Sci., 1997, 86, 1374-1378. (Pubitemid 28018317)