Drug-polymer-water interaction and its implication for the dissolution performance of amorphous solid dispersions

Molecular Pharmaceutics

Volumn 12, Issue 2, 2015, Pages 576-589

  Chen, Yuejie ^a   Liu, Chengyu ^a   Chen, Zhen ^a   Su, Ching ^b   Hageman, Michael ^b   Hussain, Munir ^b   Haskell, Roy ^b   Stefanski, Kevin ^b   Qian, Feng ^a  

^a Tsinghua University   (China)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

amorphous solid dispersion; crystallization; dissolution; drug polymer interaction; dynamic vapor sorption; Flory Huggins interaction parameter; FT IR; NMR

Indexed keywords

FELODIPINE; GRISEOFULVIN; KETOCONAZOLE; POLYMER; WATER;

AMORPHOUS SOLID DISPERSION; AREA UNDER THE CURVE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; CRYSTALLIZATION; DISPERSION; DISSOLUTION PERFORMANCE PARAMETER; DRUG ACTIVITY; DRUG SOLUBILITY; FLORY HUGGIN INTERACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROPHILICITY; IN VITRO STUDY; INFRARED RADIATION; LOADING DRUG DOSE; PHARMACOLOGICAL PARAMETERS; PREDICTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; SPRAY DRYING; SUPERSATURATION PARAMETER; TECHNOLOGY; ULTRAVIOLET SPECTROPHOTOMETRY; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

CRYSTALLIZATION; FELODIPINE; GRISEOFULVIN; KETOCONAZOLE; MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; WATER;

EID: 84961290360     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500660m     Document Type: Article

References (43)

1. Hancock, B. C. Disordered drug delivery: Destiny, dynamics and the Deborah number J. Pharm. Pharmacol. 2002, 54, 737-46
2. Ediger, M. D.; Angell, C. A.; Nagel, S. R. Supercooled liquids and glasses J. Phys. Chem. 1996, 100 (31) 13200-13212
3. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 1997, 86 (1) 1-12
4. Yu, L. Amorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Delivery Rev. 2001, 48 (1) 27-42
5. Zhou, D.; 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 (8) 1863-1872
6. 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, 37 (3-4) 492-8
7. 13C nuclear magnetic resonance relaxation time and the relaxation time obtained from the heating rate dependence of the glass transition temperature J. Pharm. Sci. 2001, 90 (6) 798-806
8. Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis J. Pharm. Sci. 2010, 99 (3) 1254-1264
9. Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals Pharm. Res. 2010, 27 (12) 2704-14
10. Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals, part 3: Is maximum solubility advantage experimentally attainable and sustainable? J. Pharm. Sci. 2011, 100 (10) 4349-4356
11. Qian, F.; Huang, J.; Hussain, M. A. Drug-polymer solubility and miscibility: Stability consideration and practical challenges in amorphous solid dispersion development J. Pharm. Sci. 2010, 99 (7) 2941-2947
12. Taylor, L. S.; Zografi, G. Sugar-polymer hydrogen bond interactions in lyophilized amorphous mixtures J. Pharm. Sci. 1998, 87 (12) 1615-1621
13. Marsac, P. J.; Konno, H.; Taylor, L. S. A comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 2006, 23 (10) 2306-16
14. Taylor, L. S.; Zografi, G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions Pharm. Res. 1997, 14 (12) 1691-98
15. Konno, H.; Taylor, L. S. Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine J. Pharm. Sci. 2006, 95 (12) 2692-705
16. Konno, H.; Taylor, L. S. Ability of different polymers to inhibit the crystallization of amorphous felodipine in the presence of moisture Pharm. Res. 2008, 25 (4) 969-78
17. Khougaz, K.; Clas, S.-D. Crystallization inhibition in solid dispersions of MK-0591 and poly(vinylpyrrolidone) polymers J. Pharm. Sci. 2000, 89 (10) 1325-1334
18. Rumondor, A. C. F.; Taylor, L. S. Effect of polymer hygroscopicity on the phase behavior of amorphous solid dispersions in the presence of moisture Mol. Pharmaceutics 2010, 7 (2) 477-90
19. Jackson, M. J.; Toth, S. J.; Kestur, U. S.; Huang, J.; Qian, F.; Hussain, M. A.; Simpson, G. J.; Taylor, L. S. Impact of polymers on the precipitation behavior of highly supersaturated aqueous danazol solutions Mol. Pharmaceutics 2014, 11 (9) 3027-38
20. Rumondor, A. C. F.; Marsac, P. J.; Stanford, L. A.; Taylor, L. S. Phase behavior of poly(vinylpyrrolidone) containing amorphous solid dispersions in the presence of moisture Mol. Pharmaceutics 2009, 6 (5) 1492-1505
21. Marsac, P. J.; Rumondor, A. C.; Nivens, D. E.; Kestur, U. S.; Stanciu, L.; Taylor, L. S. Effect of temperature and moisture on the miscibility of amorphous dispersions of felodipine and poly(vinyl pyrrolidone) J. Pharm. Sci. 2010, 99 (1) 169-85
22. Vasanthavada, M.; Tong, W.-Q.; Joshi, Y.; Kislalioglu, M. S. Phase behavior of amorphous molecular dispersions II: Role of hydrogen bonding in solid solubility and phase separation kinetics Pharm. Res. 2005, 22 (3) 440-448
23. Qian, F.; Wang, J.; Hartley, R.; Tao, J.; Haddadin, R.; Mathias, N.; Hussain, M. Solution behavior of PVP-VA and HPMC-AS-Based amorphous solid dispersions and their bioavailability implications Pharm. Res. 2012, 29 (10) 2765-76
24. Newman, A.; Knipp, G.; Zografi, G. Assessing the performance of amorphous solid dispersions J. Pharm. Sci. 2012, 101 (4) 1355-77
25. Friesen, D. T.; Shanker, R.; Crew, M.; Smithey, D. T.; Curatolo, W. J.; Nightingale, J. A. S. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: An overview Mol. Pharmaceutics 2008, 5 (6) 1003-1019
26. Ilevbare, G. A.; Taylor, L. S. Liquid-liquid phase separation in highly supersaturated aqueous solutions of poorly water-soluble drugs: Implications for solubility enhancing formulations Cryst. Growth Des. 2013, 13 (4) 1497-1509
27. Alonzo, D. E.; Zhang, G. G.; Zhou, D.; Gao, Y.; Taylor, L. S. Understanding the behavior of amorphous pharmaceutical systems during dissolution Pharm. Res. 2010, 27 (4) 608-18
28. Alonzo, D. E.; Gao, Y.; Zhou, D.; Mo, H.; Zhang, G. G.; Taylor, L. S. Dissolution and precipitation behavior of amorphous solid dispersions J. Pharm. Sci. 2011, 100 (8) 3316-31
29. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Maintaining supersaturation in aqueous drug solutions: Impact of different polymers on induction times Cryst. Growth Des. 2013, 13 (2) 740-751
30. Alonzo, D. E.; Raina, S.; Zhou, D.; Gao, Y.; Zhang, G. G. Z.; Taylor, L. S. Characterizing the impact of hydroxypropylmethyl cellulose on the growth and nucleation kinetics of felodipine from supersaturated solutions Cryst. Growth Des. 2012, 12 (3) 1538-1547
31. Simonelli, A. P.; Mehta, S. C.; Higuchi, W. I. Dissolution rates of high energy polyvinylpyrrolidone(PVP) sulfathiazole coprecipitates J. Pharm. Sci. 1969, 58, 538-549
32. Sun, Y.; Tao, J.; Zhang, G. G.; Yu, L. Solubilities of crystalline drugs in polymers: An improved analytical method and comparison of solubilities of indomethacin and nifedipine in PVP, PVP/VA, and PVAc J. Pharm. Sci. 2010, 99 (9) 4023-31
33. Zhang, J.; Zografi, G. The relationship between "BET"- and "Free volume"-Derived parameters for water vapor absorption into amorphous solids J. Pharm. Sci. 2000, 89 (8) 1063-1072
34. Hancock, B. C.; Zografi, G. The use of solution theories for predicting water vapor absorption by amorphous pharmaceutical solids: A test of the Flory-Huggins and Vrentas Models Pharm. Res. 1993, 10 (9) 1262-1267
35. Van den Mooter, G.; Wuyts, M.; Blaton, N.; Busson, R.; Grobet, P.; Augustijns, P.; Kinget, R. Physical stabilisation of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25 Eur. J. Pharm. Sci. 2001, 12 (3) 261-269
36. 13C NMR data for felodipine and its derivatives Magn. Reson. Chem. 2001, 39 (7) 406-410
37. Baird, J. A.; Van Eerdenbrugh, B.; Taylor, L. S. A classification system to assess the crystallization tendency of organic molecules from undercooled melts J. Pharm. Sci. 2010, 99 (9) 3787-806
38. Zhou, D.; Zhang, G. G. Z.; Law, D.; Grant, D. J. W.; Schmitt, E. A. Thermodynamics, molecular mobility and crystallization kinetics of amorphous griseofulvin Mol. Pharmaceutics 2008, 5 (6) 927-936
39. Klug, D. D. Thermodynamics. Glassy water Science 2001, 294 (5550) 2305-6
40. Bevernage, J.; Forier, T.; Brouwers, J.; Tack, J.; Annaert, P.; Augustijns, P. Excipient-mediated supersaturation stabilization in human intestinal fluids Mol. Pharmaceutics 2011, 8 (2) 564-70
41. Huggins, M. L. Thermodynamic properties of solutions of long-chain compounds Ann. N.Y. Acad. Sci. 1942, 43 (1) 1-32
42. Flory, P. J. Thermodynamics of high polymer solutions J. Chem. Phys. 1942, 10 (1) 51-61
43. Hosono, T.; Tsuchiya, S.; Matsumaru, H. Model of interaction of ajmaline with polyvinylpyrrolidone J. Pharm. Sci. 1980, 69 (7) 824-826