Role of the Strength of Drug-Polymer Interactions on the Molecular Mobility and Crystallization Inhibition in Ketoconazole Solid Dispersions

Molecular Pharmaceutics

Volumn 12, Issue 9, 2015, Pages 3339-3350

  Mistry, Pinal ^a   Mohapatra, Sarat ^a   Gopinath, Tata ^b   Vogt, Frederick G ^c   Suryanarayanan, Raj ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

^c Morgan Lewis Bockius LLP C   (United States)

Author keywords

amorphous solid dispersions; crystallization; dielectric spectroscopy; hydrogen bonding; infrared spectroscopy; ionic interaction; ketoconazole; molecular mobility; solid state nuclear magnetic resonance

Indexed keywords

KETOCONAZOLE; POLYMER; 2 HYDROXYETHYL METHACRYLATE; ACRYLIC ACID RESIN; CARBOPOL 940; METHACRYLIC ACID DERIVATIVE; POVIDONE;

AMORPHOUS SOLID DISPERSION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; HYDROGEN BOND; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; TITRIMETRY; X RAY POWDER DIFFRACTION; CHEMISTRY; DRUG INTERACTION; DRUG STABILITY; PHASE TRANSITION; X RAY DIFFRACTION;

ACRYLIC RESINS; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG INTERACTIONS; DRUG STABILITY; HYDROGEN BONDING; KETOCONAZOLE; METHACRYLATES; PHASE TRANSITION; POLYMERS; POVIDONE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; X-RAY DIFFRACTION;

EID: 84941101436     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.5b00333     Document Type: Article

References (56)

1. Kawabata, Y.; Wada, K.; Nakatani, M.; Yamada, S.; Onoue, S. Formulation design for poorly water-soluble drugs based on biopharmaceutics classification system: Basic approaches and practical applications Int. J. Pharm. 2011, 420, 1-10
2. Bhardwaj, S. P.; Arora, K. K.; Kwong, E.; Templeton, A.; Clas, S. D.; Suryanarayanan, R. Mechanism of amorphous itraconazole stabilization in polymer solid dispersions: Role of molecular mobility Mol. Pharmaceutics 2014, 11, 4228-4237
3. Kothari, K.; Ragoonanan, V.; Suryanarayanan, R. The role of drug-polymer hydrogen-bonding interactions on the molecular mobility and physical stability of nifedipine solid dispersions Mol. Pharmaceutics 2015, 12, 162-170
4. Khougaz, K.; Clas, S. Crystallization inhibition in solid dispersions of MK-0591 and poly(vinylpyrrolidone) polymers J. Pharm. Sci. 2000, 89, 1325-1334
5. Miyazaki, T.; Yoshioka, S.; Aso, Y.; Kojima, S. Ability of polyvinylpyrrolidone and polyacrylic acid to inhibit the crystallization of amorphous acetaminophen J. Pharm. Sci. 2004, 93, 2710-2717
6. Taylor, L. S.; Zografi, G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions Pharm. Res. 1997, 14, 1691-1698
7. Kestur, U. S.; Taylor, L. S. Role of polymer chemistry in influencing crystal growth rates from amorphous felodipine CrystEngComm 2010, 12, 2390-2397
8. Trasi, N. S.; Taylor, L. S. Effect of polymers on nucleation and crystal growth of amorphous acetaminophen CrystEngComm 2012, 14, 5188-5197
9. Gupta, M. K.; Vanwert, A.; Bogner, R. H. Formation of physically stable amorphous drugs by milling with Neusilin J. Pharm. Sci. 2003, 92, 536-551
10. Bahl, D.; Bogner, R. H. Amorphization of indomethacin by cogrinding with Neusilin US2: Amorphization kinetics, physical stability, and mechanism Pharm. Res. 2006, 23, 2317-2325
11. Maclean, J.; Medina, C.; Daurio, D.; Alvarez-Nunez, F.; Jona, J.; Munson, E.; Nagapudi, K. Manufacture and performance evaluation of a stable amorphous complex of an acidic drug molecule and Neusilin J. Pharm. Sci. 2011, 100, 3332-3344
12. Mallick, S.; Pattnaik, S.; Swain, K.; De, P. K.; Saha, A.; Ghoshal, G.; Mondal, A. Formation of physically stable amorphous phase of ibuprofen by solid-state milling with kaolin Eur. J. Pharm. Biopharm. 2008, 68, 346-351
13. Weuts, I.; Kempen, D.; Verreck, G.; Peeters, J.; Brewster, M.; Blaton, N.; Van den Mooter, G. Salt formation in solid dispersions consisting of polyacrylic acid as a carrier and three basic model compounds resulting in very high glass transition temperatures and constant dissolution properties upon storage Eur. J. Pharm. Sci. 2005, 25, 387-393
14. Yoo, S. U.; Krill, S. L.; Wang, Z.; Telang, C. Miscibility/stability considerations in binary solid dispersion systems composed of functional excipients towards the design of multicomponent amorphous systems J. Pharm. Sci. 2009, 98, 4711-4723
15. Wegiel, L. A.; Mauer, L. J.; Edgar, K. J.; Taylor, L. S. Crystallization of amorphous solid dispersions of resveratrol during preparation and storage-Impact of different polymers J. Pharm. Sci. 2013, 102, 171-184
16. Sarode, A. L.; Sandhu, H.; Shah, N.; Malick, W.; Zia, H. Hot melt extrusion for amorphous solid dispersions: Temperature and moisture activated drug-polymer interactions for enhanced stability Mol. Pharmaceutics 2013, 10, 3665-3675
17. Liu, H.; Zhang, X.; Suwardie, H.; Wang, P.; Gogos, C. G. Miscibility studies of indomethacin and Eudragit(R) E PO by thermal, rheological, and spectroscopic analysis J. Pharm. Sci. 2012, 101, 2204-2212
18. Matsumoto, T.; Zografi, G. Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinyl-acetate) in relation to indomethacin crystallization Pharm. Res. 1999, 16, 1722-1728
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
20. Kothari, K.; Ragoonanan, V.; Suryanarayanan, R. Influence of molecular mobility on the physical stability of amorphous pharmaceuticals in the supercooled and glassy states Mol. Pharmaceutics 2014, 11, 3048-3055
21. Bhardwaj, S. P.; Arora, K. K.; Kwong, E.; Templeton, A.; Clas, S. D.; Suryanarayanan, R. Correlation between molecular mobility and physical stability of amorphous itraconazole Mol. Pharmaceutics 2013, 10, 694-700
22. Martin, F. A.; Pop, M. M.; Borodi, G.; Filip, X.; Kacso, I. Ketoconazole salt and co-crystals with enhanced aqueous solubility Cryst. Growth Des. 2013, 13, 4295-4304
23. Bhugra, C.; Shmeis, R.; Krill, S. L.; Pikal, M. J. Predictions of onset of crystallization from experimental relaxation times I-Correlation of molecular mobility from temperatures above the glass transition to temperatures below the glass transition Pharm. Res. 2006, 23, 2277-2290
24. Kanaujia, P.; Lau, G.; Ng, W. K.; Widjaja, E.; Hanefeld, A.; Fischbach, M.; Maio, M.; Tan, R. B. Nanoparticle formation and growth during in vitro dissolution of ketoconazole solid dispersion J. Pharm. Sci. 2011, 100, 2876-2885
25. Goh, H. W.; Goh, S. H.; Xu, G. Q. Hydrogen bonding and hydrophobic interactions between [60]fullerenated poly(2-hydroxyethyl methacrylate) and poly(1-vinylimidazole) or poly(4-vinylpyridine) J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 4316-4327
26. Van den Mooter, G.; Wuyts, M.; Blaton, N.; Busson, R.; Grobet, P.; Augustijns, P.; Kinget, R. Physical stabilization of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25 Eur. J. Pharm. Sci. 2001, 12, 261-269
27. Marsac, P. J.; Li, T.; Taylor, L. S. Estimation of drug-polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters Pharm. Res. 2009, 26, 139-151
28. Delaglio, F.; Grzesiek, S.; Vuister, G. W.; Zhu, G.; Pfeifer, J.; Bax, A. NMRPipe: A multidimensional spectral processing system based on UNIX pipes J. Biomol. NMR 1995, 6, 277-293
29. Wishart, D. S.; Bigam, C. G.; Yao, J.; Abildgaard, F.; Dyson, H. J.; Oldfield, E.; Markley, J. L.; Sykes, B. D. 1H, 13C, and 15N chemical shift referencing in biomolecular NMR J. Biomol. NMR 1995, 6, 135-140
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
31. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. A comparison of models for calculating nuclear magnetic resonance shielding tensors J. Chem. Phys. 1996, 104, 5497-5509
32. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
33. Kothari, K.; Ragoonanan, V.; Suryanarayanan, R. Dielectric spectroscopy of small molecule pharmaceuticals-Effect of sample configuration J. Pharm. Sci. 2014, 103, 3190-3196
34. Havriliak, S.; Negami, S. A complex plane analysis of α-dispersions in some polymer systems J. Polym. Sci., Part C: Polym. Symp. 1966, 14 (1) 99-117
35. Rumondor, A. C.; Ivanisevic, I.; Bates, S.; Alonzo, D. E.; Taylor, L. S. Evaluation of drug-polymer miscibility in amorphous solid dispersion systems Pharm. Res. 2009, 26, 2523-2534
36. Crowley, K. J.; Zografi, G. The effect of low concentrations of molecularly dispersed poly(vinylpyrrolidone) on indomethacin crystallization from the amorphous state Pharm. Res. 2003, 20, 1417-1422
37. Yoshioka, M.; Hancock, B. C.; Zografi, G. Inhibition of indomethacin crystallization in poly(vinylpyrrolidone) coprecipitates J. Pharm. Sci. 1995, 84, 983-986
38. Bhugra, C.; Shmeis, R.; Krill, S. L.; Pikal, M. J. Prediction of onset of crystallization from experimental relaxation times. II. Comparison between predicted and experimental onset times J. Pharm. Sci. 2008, 97, 455-472
39. Fox, T. G. Influence of diluent and of copolymer composition on the glass temperature of a polymer system Bull. Am. Phys. Soc. 1956, 1, 22060-26218
40. Glipa, X.; Bonnet, B.; Mula, B.; Jones, D. J.; Rozière, J. Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole J. Mater. Chem. 1999, 9, 3045-3049
41. Bouchet, R.; Siebert, E. Proton conduction in acid-doped polybenzimidazole Solid State Ionics 1999, 118, 287-299
42. Asensio, J. A.; Borrós, S.; Gómez-Romero, P. Proton-conducting polymers based on benzimidazoles and sulfonated benzimidazoles J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3703-3710
43. Dong, J.; Ozaki, Y.; Nakashima, K. Infrared, Raman, and near-infrared spectroscopic evidence for the coexistence of various hydrogen-bond forms in poly(acrylic acid) Macromolecules 1997, 30, 1111-1117
44. Stothers, J. Carbon-13 NMR Spectroscopy; Academic Press: New York, 1972; Vol. 24, p 299.
45. Carbon-13 NMR Spectroscopy; Kalinowski, H.; Berger, S.; Braun, S., Eds.; John Wiley and Sons: New York, 1998; p 198.
46. Schuster, I. I.; Roberts, J. D. Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts in imidazoles J. Org. Chem. 1979, 44, 3864-3867
47. Berger, S.; Braun, S.; Kalinowski, H. NMR Spectroscopy of the Nonmetallic Elements; Wiley: New York, 1997.
48. Alei, M., Jr; Morgan, L.; Wageman, W.; Whaley, T. The pH dependence of nitrogen-15 NMR shifts and coupling constants in aqueous imidazole and 1-methylimidazole. Comments on estimation of tautomeric equilibrium constants for aqueous histidine J. Am. Chem. Soc. 1980, 102, 2881-2887
49. Yang, Z.; Han, C. D. Rheology of miscible polymer blends with hydrogen bonding Macromolecules 2008, 41, 2104-2118
50. Wang, L.; Zhao, L.; Liu, M.; Chen, R.; Yang, Y.; Gu, Y. Multicomponent hydrogen-bonding salts formed between imidazole and aromatic acids: Synthons cooperation and crystal structures Sci. China: Chem. 2012, 55, 2115-2122
51. Angell, C. A.; Ngai, K. L.; McKenna, G. B.; McMillan, P. F.; Martin, S. W. Relaxation in glass-forming liquids and amorphous solids J. Appl. Phys. 2000, 88, 3113-3157
52. 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, 3787-3806
53. Song, Y.; Yang, X.; Chen, X.; Nie, H.; Byrn, S.; Lubach, J. W. Investigation of drug-excipient interactions in lapatinib amorphous solid dispersions using solid-state NMR spectroscopy Mol. Pharmaceutics 2015, 12, 857-866
54. Dieterich, D.; Keberle, W.; Witt, H. Polyurethane ionomers, a new class of block polymers Angew. Chem., Int. Ed. Engl. 1970, 9, 40-50
55. Longworth, R.; Morawetz, H. Polymer association. IV. Hydrogen bonding and melt viscosities in copolymers of styrene with methacrylic acid J. Polym. Sci. 1958, 29, 307-319
56. Shohamy, E.; Eisenberg, A. The effect of ion aggregation on some melt properties of styrene ionomers J. Polym. Sci., Polym. Phys. Ed. 1976, 14, 1211-1220