Physical stability of drugs after storage above and below the glass transition temperature: Relationship to glass-forming ability

International Journal of Pharmaceutics

Volumn 495, Issue 1, 2015, Pages 312-317

  Alhalaweh, Amjad ^a   Alzghoul, Ahmad ^b   Mahlin, Denny ^a   Bergström, Christel A S ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

Amorphous; Computational prediction; Glass forming ability; Physical stability; SVM

Indexed keywords

ACEMETACIN; ARIPIPRAZOLE; BICALUTAMIDE; BUDESONIDE; CAPTOPRIL; CARVEDILOL; CELECOXIB; CHLORAMPHENICOL; CHLORHEXIDINE; CINNARIZINE; CLEMASTINE; CLOTRIMAZOLE; DANAZOL; DRUG; EMTRICITABINE; ESTRADIOL; EZETIMIBE; FELODIPINE; FLUORESCAMINE; FLURBIPROFEN; NIFEDIPINE; PARACETAMOL; PIMOZIDE; TAMOXIFEN; TENOFOVIR; TESTOSTERONE; TETRAHYDROLIPSTATIN; TINIDAZOLE; TOLAZAMIDE; UNINDEXED DRUG; GLASS;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STABILITY; DRUG STORAGE; ENTHALPY; GLASS TRANSITION TEMPERATURE; HEATING; MELTING POINT; MOLECULAR SIZE; MOLECULAR WEIGHT; PREDICTION; PRIORITY JOURNAL; SOLID STATE; SUPPORT VECTOR MACHINE; TEMPERATURE SENSITIVITY; THERMODYNAMICS; CHEMISTRY; STRUCTURE ACTIVITY RELATION; TEMPERATURE; TRANSITION TEMPERATURE;

CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG STABILITY; GLASS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT VECTOR MACHINE; TEMPERATURE; THERMODYNAMICS; TRANSITION TEMPERATURE;

EID: 84941104993     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2015.08.101     Document Type: Article

References (32)

1. A. Alhalaweh, A. Alzghoul, and W. Kaialy Data mining of solubility parameters for computational prediction of drug-excipient miscibility Drug. Dev. Ind. Pharm. 40 2013 p904 909
2. A. Alhalaweh, A. Alzghoul, K. Waseem, M. Denny, and C.A.S. Bergstrom Computational predictions of glass-forming ability and crystallization tendency of drug molecules Mol. Pharm. 11 2014 3123 3132
3. M. Alonso, P. Geerlings, and F. De Proft Exploring the structure-aromaticity relationship in Hückel and Möbius N-fused pentaphyrins using DFT Phys. Chem. Chem. Phys. 16 2014 14396 14407
4. A. Alzghoul, A. Alhalaweh, D. Mahlin, and C.A. Bergström Experimental and computational prediction of glass transition temperature of drugs J. Chem. Inf. Model. 54 2014 3396 3403
5. V. Andronis, and G. Zografi The molecular mobility of supercooled amorphous indomethacin as a function of temperature and relative humidity Pharm. Res. 15 1998 p835 842
6. C. Angell Perspective on the glass transition J. Phys. Chem. Solids 49 1988 p863 871
7. K.R. Back, R.J. Davey, T. Grecu, C.A. Hunter, and L.S. Taylor Molecular conformation and crystallization: the case of ethenzamide Cryst. Growth Des. 12 2012 6110 6117
8. J.A. Baird, B. Van Eerdenbrugh, and L.S. Taylor A classification system to assess the crystallization tendency of organic molecules from undercooled melts J. Pharm. Sci. 99 2010 3787 3806
9. I. Bar, and J. Bernstein Modification of crystal packing and molecular conformation via systematic substitution Tetrahedron 43 1987 p1299 1305
10. J. Bernstein, and A. Hagler Conformational polymorphism. The influence of crystal structure on molecular conformation J. Am. Chem. Soc. 100 1978 p673 681
11. C. Bhugra, and M.J. Pikal Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state J. Pharm. Sci. 97 2008 p1329 1349
12. K.A. Graeser, J.E. Patterson, J.A. Zeitler, K.C. Gordon, and T. Rades Correlating thermodynamic and kinetic parameters with amorphous stability Eur. J. Pharm. Sci. 37 2009 492 498
13. B.C. Hancock, G.T. Carlson, D.D. Ladipo, B.A. Langdon, and M.P. Mullarney Comparison of the mechanical properties of the crystalline and amorphous forms of a drug substance Int. J. Pharm. 241 2002 p73 85
14. B.C. Hancock, K. Christensen, and S.L. Shamblin Estimating the critical molecular mobility temperature (TK) of amorphous pharmaceuticals Pharm. Res. 15 1998 1649 1651
15. B.C. Hancock, and M. Parks What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17 2000 397 404
16. B.C. Hancock, S.L. Shamblin, and G. Zografi Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures Pharm. Res. 12 1995 799 806
17. J.D. Hoffman Thermodynamic driving force in nucleation and growth processes J. Chem. Phys. 29 1958 p1192 1193
18. W. Kauzmann The nature of the glassy state and the behavior of liquids at low temperatures Chem. Rev. 43 1948 219 256
19. K. Kawakami, T. Harada, K. Miura, Y. Yoshihashi, E. Yonemochi, K. Terada, and H. Moriyama Relationship between crystallization tendencies during cooling from melt and isothermal storage: toward a general understanding of physical stability of pharmaceutical glasses Mol. Pharm. 11 2014 1835 1843
20. K. Kothari, V. Ragoonanan, and R. Suryanarayanan Influence of molecular mobility on the physical stability of amorphous pharmaceuticals in the supercooled and glassy states Mol. Pharm. 11 2014 3048 3055
21. D. Mahlin, and C.A. Bergström Early drug development predictions of glass-forming ability and physical stability of drugs Eur. J. Pharm. Sci. 49 2013 323 332
22. D. Mahlin, S. Ponnambalam, M. Heidarian Höckerfelt, and C.A. Bergström Toward in silico prediction of glass-forming ability from molecular structure alone: a screening tool in early drug development Mol. Pharm. 8 2011 498 506
23. P.J. Marsac, H. Konno, and L.S. Taylor A comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 23 2006 2306 2316
24. P.J. Marsac, S.L. Shamblin, and L.S. Taylor Theoretical and practical approaches for prediction of drug-polymer miscibility and solubility Pharm. Res. 23 2006 2417 2426
25. M.L. Nascimento, L.A. Souza, E.B. Ferreira, and E.D. Zanotto Can glass stability parameters infer glass forming ability? J. Non-Cryst. Solids 351 2005 3296 3308
26. J.T. Pulkkinen, R. Laatikainen, M.J. Ahlgrén, M. Peräkylä, and J.J. Vepsäläinen Conformational flexibility and role of aromatic?aromatic interactions in the crystal packing of the coordination compounds of some novel quadridentate Schiff bases J. Chem. Soc. Perkin Trans. 2 2000 777 784
27. J.A. Suykens, and J. Vandewalle Least squares support vector machine classifiers Neural Process. Lett. 9 1999 293 300
28. N.S. Trasi, J.A. Baird, U.S. Kestur, and L.S. Taylor Factors influencing crystal growth rates from undercooled liquids of pharmaceutical compounds J. Phys. Chem. B 118 2014 9974 9982
29. M.C. Weinberg Glass-forming ability and glass stability in simple systems J. Non-Cryst. Solids 167 1994 81 88
30. M. Yoshioka, B.C. Hancock, and G. Zografi Crystallization of indomethacin from the amorphous state below and above its glass transition temperature J. Pharm. Sci. 83 1994 1700 1705
31. L. Yu Amorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Deliv. Rev. 48 2001 27 42
32. D. Zhou, G.G. Zhang, D. Law, D.J. Grant, and E.A. Schmitt Physical stability of amorphous pharmaceuticals: importance of configurational thermodynamic quantities and molecular mobility J. Pharm. Sci. 91 2002 1863 1872