Theoretical and experimental investigation on the solid solubility and miscibility of naproxen in poly(vinylpyrrolidone)

Molecular Pharmaceutics

Volumn 7, Issue 4, 2010, Pages 1133-1148

  Paudel, Amrit ^a   Van Humbeeck, Jan ^a   Van Den Mooter, Guy ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

amorphous miscibility; drug polymer interaction; melting point depression; moisture sorption; Solid dispersion; solid solubility

Indexed keywords

1 METHYL 2 PYRROLIDINONE; NAPROXEN; PLASTICIZER; POLYMER; POVIDONE;

ARTICLE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; DRUG STRUCTURE; MELTING POINT; MISCIBILITY; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SOLUBILITY; SPRAY DRYING; TEMPERATURE MEASUREMENT; THERMAL ANALYSIS; THERMODYNAMICS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; NAPROXEN; POLYMERS; PYRROLIDINONES; SOLUBILITY; TRANSITION TEMPERATURE;

EID: 77955243354     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100013p     Document Type: Article

References (51)

1. Chiou, W. L.; Riegelman, S. Pharmaceutical Applications of Solid Dispersion Systems J. Pharm. Sci. 1971, 60, 1281-1302
2. Leuner, C.; Dressman, J. Improving Drug Solubility for Oral Delivery using Solid Dispersions Eur. J. Pharm. Biopharm. 2000, 50, 47-60
3. Sethia, S.; Squillante, E. Solid Dispersions: Revival with Greater Possibilities and Applications in Oral Drug Delivery Crit. Rev. Ther. Drug. Carrier Syst. 2003, 20, 215-247
4. Serajuddin, A. T. M. Solid Dispersion of poorly Water-soluble Drugs: Early Promises, Subsequent Problems, and Recent Breakthroughs J. Pharm. Sci. 2000, 88, 1058-1066
5. Khougaz, K.; Clas, S. D. Crystallization Inhibition in Solid Dispersions of MK-0591 and Poly (vinylpyrrolidone) Polymers J. Pharm. Sci. 2000, 89, 1325-1334
6. Janssens, S.; Van den Mooter, G. Review: Physical Chemistry of Solid Dispersions J. Pharm. Pharmacol. 2009, 61, 1571-1586
7. Marsac, P. J.; Shamblin, S. L.; Taylor, L. S. Theoretical and Practical Approaches for Prediction of Drug-Polymer Miscibility and Solubility Pharm. Res. 2006, 23, 2417-2426
8. 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
9. Velaz, I.; Sanchez, M.; Martin, C.; Martinez-Oharriz, M. C.; Zornoza, A. Interaction of Naproxen with Vinyl Pyrrolidone and Î-Cyclodextrin: a Fluorimetric Study Int. J. Pharm. 1997, 153, 211-217
10. Bettinetti, G. P.; Mura, P. Dissolution Properties of Naproxen in Combinations with Polyvinlypyrrolidone Drug Dev. Ind. Pharm. 1994, 20, 1353-1366
11. Bettinetti, P.; Mura, P.; Liguori, A.; Bramanti, G. Solubilization and Interaction of naproxen with Polyvinylpyrrolidone in Aqueous Solution and in Solid State Farmaco Prat. 1988, 43, 331-343
12. Bogdanova, S.; Pajeva, I.; Nikolova, P.; Tsakovska, I.; MuÌ̂ller, B. Interactions of Poly(vinylpyrrolidone) with Ibuprofen and Nap roxen: Experimental and Modeling Studies Pharm. Res. 2005, 22, 806-815
13. Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, 1953.
14. Hildebrand, H. The Term a ̃Regular Solutionâ Nature 1951, 168, 868
15. Greenhalgh, D. J.; Williams, A. C.; Timmins, P.; York, P. Solubility Parameters as Predictors of Miscibility in Solid Dispersions J. Pharm. Sci. 1999, 88, 1182-1190
16. Muruganandham, M.; Chen, S. H.; Wu, J. J. Mineralization of N-methyl-2-pyrolidone by Advanced Oxidation Processes Sep. Purif. Technol. 2007, 55, 360-367 (Pubitemid 46727089)
17. Pinal, R. Entropy of Mixing and the Glass Transition of Amorphous Mixtures Entropy 2008, 10, 207-223
18. Gordon, M.; Taylor, J. S. Ideal Copolymers and the Second-order Transitions of Synthetic rubbers. I. Non-crystalline polymers J. Appl. Chem. 1952, 2, 493-500
19. Simha, R.; Boyer, R. F. On a General Relation Involving the Glass Temperature and Coefficients of Expansion of Polymers J. Chem. Phys. 1962, 37, 1003-1007
20. 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, 440-448
21. Forster, A.; Hempenstall, J.; Rades, T. Comparison of the Gordon-Taylor and Couchman-Karasz Equations for Prediction of the Glass Transition Temperature of Glass Solutions of Drug and Polyvinylpyrrolidone Prepared by Melt Extrusion Pharmazie 2003, 58, 838-839
22. Feldsteina, M. M.; Roos, A.; Chevallier, C.; Creton, C.; Dormidontova, E. E. Relation of glass Transition Temperature to the Hydrogen Bonding degree and Energy in Poly (N-vinyl pyrrolidone) blends with Hydroxyl-containing Plasticizers: 3. Analysis of two Glass Transition Temperatures featured for PVP Solutions in liquid Poly (ethylene glycol) Polymer 2003, 44, 1819-1834
23. Schneider, H. A. Conformational Entropy Contributions to the Glass Temperature of Blends of Miscible Polymers J. Res. Natl. Inst. Stand. Technol. 1997, 102, 229-248
24. Couchman, P. R.; Karasz, F. E. A Classical Thermodynamic Discussion of the effect of Composition on Glass Transition Temperatures Macromolecules 1978, 11, 117-119
25. Tanaka, N. Conformational effects on Glass Transition Temperature and Relaxation Phenomena of Polymers Polymer 1978, 19, 770-772
26. Neau, S. H.; Flynn, G. L.; Yalkowsky, S. H. The influence of Heat Capacity Assumptions on the Estimation of Solubility Parameters from Solubility data Int. J. Pharm. 1989, 49, 223-229
27. Neau, S. H.; Bhandarkar, S. V.; Hellmuth, E. W. Differential Molar Heat Capacities to test Ideal Solubility Estimations Pharm. Res. 1997, 14, 601-605
28. Hancock, B. C.; Parks, M. What is the true Solubility Advantage for Amorphous Pharmaceuticals Pharm. Res. 2000, 17, 397-404
29. LuÌ̂der, K.; Lindfors, L.; Westergren, J.; Nordholm, S.; Kjellander, R. In Silico Prediction of Drug Solubility. 3. Free Energy of Solvation in pure Amorphous Matter J. Phys. Chem. B 2007, 111, 7303-7311 (Pubitemid 47152517)
30. Fedors, R. F. A Method for Estimating both the Solubility Parameters and Molecular Volumes of Liquids Polym. Eng. Sci. 1974, 14, 147-154
31. Nishi, T.; Wang, T. T. Melting-Point Depression and Kinetic Effects of Cooling on Crystallization in Poly (vinylidene fluoride)-Poly (methyl methacrylate) Mixtures Macromolecules 1975, 8, 909-915
32. Wertheim, M. S. Fluids with highly Directional Attractive Forces. I. Statistical Thermodynamics J. Stat. Phys. 1984, 35, 19-34
33. Wertheim, M. S. Fluids with highly Directional Attractive Forces. II. Thermodynamic Perturbation Theory and Integral Equations J. Stat. Phys. 1984, 35, 35-47
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, 1262-1267
35. Crowley, K. J.; Zografi, G. Water Vapor Absorption into Amorphous Hydrophobic Drug/Poly (vinylpyrrolidone) Dispersions J. Pharm. Sci. 2002, 91, 2150-2165
36. BuÌ̂hler, V. Polyvinylpyrrolidone Excipients for Pharmaceuticals Povidone, Crospovidone and Copovidone; Springer-Verlag Publishing Co.: Berlin Heidelberg, 2005; pp 88 -' 108.
37. Gashi, Z.; Censi, R.; Malaj, L.; Gobetto, R.; Mozzicafreddo, M.; Angeletti, M.; Masic, A.; Di Martino, P. Differences in the Interaction between Aryl Propionic Acid Derivatives and Poly (vinylpyrrolidone) K30: A Multi-methodological Approach J. Pharm. Sci. 2009, 11, 4216-4228
38. LemaiÌtre, V.; Smith, M. E.; Watts, A. A Review of Oxygen-17 Solid-State NMR of Organic Materials-Towards Biological Applications Solid State Nucl. Magn. Reson. 2004, 26, 215-235
39. Velazquez, M. M.; Valero, M.; RodriÌguez, L. J.; Costa, S. M.; Santos, M. A. Hydrogen Bonding in a Non-Steroidal Anti-Inflammatory Drug-Naproxen J. Photochem. Photobiol. B 1995, 29, 23-31
40. Tsivintzelis, I.; Economou, I. G.; Kontogeorgis, G. M. Modeling the Phase Behavior in Mixtures of Pharmaceuticals with Liquid or Supercritical solvents J. Phys. Chem. B 2009, 113, 6446-6458
41. Chawla, G.; Bansal, A. K. A Comparative Assessment of Solubility Advantage from Glassy and Crystalline forms of a Water-insoluble Drug Eur. J. Pharm. Sci. 2007, 32, 45-57
42. Sengwa, R. J.; Sankhla, S. Chain Length Effect on Dynamical Structure of Poly (vinyl pyrrolidone)-Polar Solvent Mixtures in Dilute Solution of Dioxane Studied by Microwave Dielectric Relaxation Measurement PRAMANAî - ̧J. Phys. 2006, 67, 375-381
43. Panayiotou, C.; Pantoula, M.; Stefanis, E.; Tsivintzelis, I. Nonrandom Hydrogen-Bonding Model of Fluids and Their Mixtures. 1. Pure Fluids Ind. Eng. Chem. Res. 2004, 43, 6592-6606
44. Panayiotou, C.; Tsivintzelis, I.; Economou, I. G. Nonrandom Hydrogen-Bonding Model of Fluids and Their Mixtures. 2. Multicomponent Mixtures Ind. Eng. Chem. Res. 2007, 46, 2628-2636
45. Frank, T. C.; Downey, J. R.; Gupta, S. K. Quickly Screen Solvents for Organic Solids Chem. Eng. Prog. 1999, 95, 41-61
46. Chen, C.; Song, Y. Solubility Modeling with a Nonrandom Two-Liquid Segment Activity Coefficient Model Ind. Eng. Chem. Res. 2004, 43, 8354-8362
47. Klamt, A.; Eckert, F.; Hornig, M.; Beck, M. E.; Burger, T. Prediction of Aqueous Solubility of Drugs and Pesticides with COSMO-RS J. Comput. Chem. 2002, 23, 275-281
48. Wiranidchaponga, C.; Rades, T.; Kulvanich, P.; Tucker, I. G. Method of preparation does not affect the miscibility between steroid hormone and polymethacrylate Thermochim. Acta 2009, 485, 57-64
49. Available at https://lirias.kuleuven.be/bitstream/1979/2083/2/.pdf.
50. Rumondor, A. C.; 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, 1492-14505
51. 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, 169-185