Solid state solubility of miconazole in poly[(ethylene glycol)-g-vinyl alcohol] using hot-melt extrusion

Molecular Pharmaceutics

Volumn 9, Issue 10, 2012, Pages 2924-2932

  Litvinov, V M ^a   Guns, S ^b   Adriaensens, P ^c   Scholtens, B J R ^a   Quaedflieg, M P ^a   Carleer, R ^c   Van Den Mooter, G ^b  

^a DSM RESOLVE   (Netherlands)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c HASSELT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE VINYL ALCOHOL COPOLYMER; MICONAZOLE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; DRUG SOLUBILITY; HOT MELT EXTRUSION; PHARMACOLOGICAL PROCEDURES; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; TEMPERATURE; X RAY POWDER DIFFRACTION;

EID: 84870218526     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300280k     Document Type: Article

References (49)

1. Chiou, W. L.; Riegelman, S. Pharmaceutical applications of solid dispersion systems J. Pharm. Sci. 1971, 60, 1281-1302
2. Gao, P. Amorphous Pharmaceutical Solids: Characterization, Stabilization, and Development of Marketable Formulations of Poorly Soluble Drugs with Improved Oral Absorption Mol. Pharmaceutics 2008, 5, 903-904 and manuscripts in the same issue
3. Willart, J. F.; Descamps, M. Solid State Amorphization of Pharmaceuticals Mol. Pharmaceutics 2008, 5, 905-920
4. Vasanthavada, M.; Tong, W.-Q.; Joshi, Y.; Kislalioglu, M. S. Phase Behavior of Amorphous Molecular Dispersions I: Determination of the Degree and Mechanism of Solid Solubility Pharm. Res. 2004, 21, 1598-1606
5. 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
6. Fedotov, V. D.; Schneider, H. Structure and Dynamics of Bulk Polymers by NMR Methods. In NMR Basic Principles and Progress; Diehl, P.; Fluck, E.; Gunter, H.; Kosfeld, R.; Seelig, I., Eds.; Springer-Verlag: Berlin, 1989.
7. McBrierty, V. J.; Packer, K. J. Nuclear Magnetic Resonance in Solid Polymers; Cambridge University Press: Cambridge, 1993.
8. Schmidt-Rohr, K.; Spiess, H. W. Multidimensional Solid-State NMR and Polymers; Academic Press: London, 1994.
9. Byrn, S. R.; Xu, W.; Newman, A. W. Chemical Reactivity in Solid-State Pharmaceuticals: Formulation Implications Adv. Drug Delivery Rev. 2001, 48, 115-136
10. Bugay, D. E. Characterization of the Solid-State: Spectroscopic Techniques Adv. Drug Delivery Rev. 2001, 48, 43-65
11. Berendt, R. T.; Sperger, D. M.; Isbester, P. K.; Munson, E. J. Solid-State NMR Spectroscopy in Pharmaceutical Research and Analysis TrAC, Trends Anal. Chem. 2006, 25, 977-984
12. Schantz, S.; Hoppu, P.; Juppo, A. M. A Solid-State NMR Study of Phase Structure, Molecular Interactions, and Mobility in Blends of Citric Acid and Paracetamol J. Pharm. Sci. 2009, 98, 1862-1870
13. Weuts, I.; Van Dycke, F.; Voorspoels, J; De Cort, S.; Stokbrokx, S.; Leemans, R.; Brewster, M. E.; Xu, D. W.; Segmuller, B.; Turner, Y. T. A.; Roberts, C. J.; Davies, M. C.; Qi, S.; Craig, D. Q. M.; Reading, M. Physicochemical Properties of the Amorphous Drug, Cast Films, and Spray Dried Powders to Predict Formulation Probability of Success for Solid Dispersions: Etravirine J. Pharm. Sci. 2011, 100, 260-274
14. 1 Relaxation Measurements Mol. Pharmaceutics 2010, 7, 1667-1691
15. Forster, A.; Apperley, D.; Hempenstall, J.; Lancaster, R.; Rades, T. Investigation of the Physical Stability of Amorphous Drug and Drug/Polymer Melts Using Variable Temperature Solid State NMR Pharmazie 2003, 58, 761-762
16. Barich, D. H.; Davis, J. M.; Schieber, L. J.; Zell, M. T.; Munson, E. J. Investigation of Solid-State NMR Line Widths of Ibuprofen in Drug Formulations J. Pharm. Sci. 2006, 95, 1586-1594
17. Lubach, J. W.; Xu, D.; Segmuller, B. E.; Munson, E. J. Investigation of the Effects of Pharmaceutical Processing Upon Solid-State NMR Relaxation Times and Implications to Solid-State Formulation Stability J. Pharm. Sci. 2007, 96, 777-787
18. Janssens, S.; Novoa de Armas, H.; Remon, J. P.; Van den Mooter, G. The Use of a New Hydrophilic Polymer, Kollicoat IR, in the Formulation of Solid Dispersions of Itraconazole Eur. J. Pharm. Sci. 2007, 30, 288-294
19. Janssens, S.; Anné, M.; Rombaut, P.; Van den Mooter, G. Spray Drying from Complex Solvent Systems Broadens the Applicability of Kollicoat IR as a Carrier in the Formulation of Solid Dispersions Eur. J. Pharm. Sci. 2009, 37, 241-248
20. Guns, S.; Kayaert, P.; Martens, J. A.; Van Humbeeck, J.; Mathot, V.; Pijpers, T.; Zhuravlev, E.; Schick, C.; Van den Mooter, G. Characterization of the Copolymer Poly(ethyleneglycol-g-vinylalcohol) as a Potential Carrier in the Formulation of Solid Dispersions Eur. J. Pharm. Biopharm. 2010, 74, 239-247
21. Litvinov, V. M.; Penning, J. P. Phase Composition and Molecular Mobility in Nylon 6 Fibers as Studied by Proton NMR Transverse Magnetization Relaxation Macromol. Chem. Phys. 2004, 205, 1721-1734
22. Litvinov, V. M. EPDM/PP Thermoplastic Vulcanizates As Studied by Proton NMR Relaxation: Phase Composition, Molecular Mobility, Network Structure in the Rubbery Phase, and Network Heterogeneity Macromolecules 2006, 39, 8727-8741
23. Litvinov, V. M.; Persyn, O.; Miri, V.; Lefebvre, J. M. Morphology, Phase Composition, and Molecular Mobility in Polyamide Films in Relation to Oxygen Permeability Macromolecules 2010, 43, 7668-7679
24. 13C NMR of Solid Polymers Polym. Bull. 1982, 8, 253-259
25. Guns, S.; Mathot, V.; Martens, A. J.; Van den Mooter, G. Upscaling of the hot-melt extrusion process: comparison between laboratory scale and pilot scale production of solid dispersions with miconazole and Kollicoat IR Eur. J. Pharm. Biopharm. 2012, 81 (3) 674-682 10.1016/j.ejpb.2012.03.020
26. Newman, A.; Engers, D.; Bates, S.; Ivanisevic, I.; Kelly, R. C.; Zografi, G. Characterization of Amorphous API: Polymer Mixtures Using X-Ray Powder Diffraction J. Pharm. Sci. 2008, 97, 4840-4856
27. Litvinov, V. Molecular Mobility and Phase Composition in Polyolefins: From Fundamental to Applied Research. In NMR Spectroscopy of Polymers: Innovative Strategies for Complex Macromolecules; ACS Symposium Series, Vol. 1077; Cheng, H. N.; Asakura, T.; English, A. D., Eds.; American Chemical Society: Washington, DC, 2011; Chapter 11, pp 179-190.
28. Aharoni, S. M. On Entanglements of Flexible and Rodlike Polymers Macromolecules 1983, 16, 1722-1728
29. Wool, R. P. Polymer Entanglements Macromolecules 1993, 26, 1564-1569
30. Heymans, N. A Novel Look at Models for Polymer Entanglement Macromolecules 2000, 33, 4226-4234
31. 1H Solid State NMR Study Macromolecules 1999, 32, 167-180
32. Litvinov, V. M.; Soliman, M. The Effect of Storage of Poly(propylene) Pipes Under Hydrostatic Pressure and Elevated Temperatures on the Morphology, Molecular Mobility and Failure Behaviour Polymer 2005, 46, 3077-3089
33. 2 Relaxation Under Uniaxial Compression Macromolecules 2001, 34, 8468-8474
34. Hedesiu, C.; Kleppinger, R.; Demco, D. E.; Buda, A.; Blümich, B.; Remerie, K.; Litvinov, V. M. The Effect of Temperature and Annealing on the Phase Composition, Molecular Mobility and the Thickness of Domains in High-Density Polyethylene Polymer 2007, 48, 763-777
35. Hedesiu, C.; Demco, D. E.; Kleppinger, R.; Vanden Poel, G.; Gijsbers, W.; Blümich, B.; Remerie, K.; Litvinov, V. M. Effect of Temperature and Annealing on the Phase Composition, Molecular Mobility, and the Thickness of Domains in Isotactic Polypropylene Studied by Proton Solid-State NMR, SAXS, and DSC Macromolecules 2007, 40, 3977-3989
36. 13C NMR Polymer 2001, 42, 4687-4707
37. 13C NMR Investigation of the Structure and Hydrogen Bonding for Stereoregular Poly(vinyl alcohol) Films in the Hydrated State Polymer 2007, 48, 3850-3857
38. Hedesiu, C.; Demco, D. E.; Kleppinger, R.; Vanden Poel, G.; Remerie, K.; Litvinov, V. M.; Blümich, B.; Steenbakkers, R. Aging Effects on the Phase Composition and Chain Mobility of Isotactic Poly(propylene) Macromol. Mater. Eng. 2008, 293, 847-857
39. Alexy, P.; Lacík, I.; Simková, B.; Bakos, D.; Prónayova, N.; Liptaj, T.; Hanzelová, S.; Városová, M. Effect of Melt Processing on Thermo-Mechanical Degradation of Poly(vinyl alcohol)s Polym. Degrad. Stab. 2004, 85, 823-830
40. Clauss, J.; Schmidt-Rohr, K.; Spiess, H. W. Determination of Domain Sizes in Heterogeneous Polymers by Solid-State NMR Acta Polym. 1993, 44, 1-17
41. VanderHart, D. L.; McFadden, G. M. Some Perspectives on the Interpretation of Proton NMR Spin Diffusion Data in Terms of Polymer Morphologies Solid State NMR 1996, 7, 45-66
42. White, J. L.; Machowicz, M. Polymer Blend Miscibility Annu. Rep. NMR Spectrosc. 2008, 64, 189-209
43. 13C Solid-State NMR and Thermal Analysis Macromolecules 2002, 35, 3965-3970
44. Mens, R.; Adriaensens, P.; Lutsen, L.; Swinnen, A.; Bertho, S.; Ruttens, B.; D'Haen, J.; Manca, J.; Cleij, T.; Vanderzande, D.; Gelan, J. NMR Study of the Nanomorphology in Thin Films of Polymer Blends Used in Organic PV Devices: MDMO-PPV/PCBM J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 138-145
45. 13C NMR Spectra of Poly(vinyl alcohol) Polymer 2001, 42, 9855-9858
46. Ohgi, H.; Sato, T.; Hu, S.; Horii, F. Highly Isotactic Poly(vinyl alcohol) Derived from Tert-butyl Vinyl Ether. Part IV. Some Physical Properties, Structure and Hydrogen Bonding of Highly Isotactic Poly(vinyl alcohol) Films Polymer 2006, 47, 1324-1332
47. 13C NMR Investigation of the Structure and Hydrogen Bonding for Stereoregular Poly(vinyl alcohol) Films in the Hydrated State Polymer 2007, 48, 3850-3857
48. Demco, D. E.; Johannsson, A.; Tegenfeldt, J. Proton Spin Diffusion for Spatial Heterogeneity and Morphology Investigations of Polymers Solid State Nucl. Magn. Reson. 1995, 4, 13-38
49. 1H NMR Spin Diffusion Coefficients for Mobile Polymers through Transverse Relaxation. Measurements Macromolecules 1999, 32, 4686-4691