Impact of polymers on the crystallization and phase transition kinetics of amorphous nifedipine during dissolution in aqueous media

Molecular Pharmaceutics

Volumn 11, Issue 10, 2014, Pages 3565-3576

  Raina, Shweta A ^a   Alonzo, David E ^b,c   Zhang, Geoff G Z ^b   Gao, Yi ^b   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b ABBVIE INC   (United States)

^c GILEAD SCIENCES   (United States)

Author keywords

crystallization; multivariate curve resolution; polymers; polymorphism; Raman spectroscopy; solution mediated phase transformation; supersaturated solutions

Indexed keywords

ACETIC ACID; HYDROXYPROPYLMETHYLCELLULOSE; NIFEDIPINE; POLYMER; POVIDONE; POLYVINYLPOLYPYRROLIDONE;

ANALYTIC METHOD; AQUEOUS SOLUTION; ARTICLE; CHEMOMETRIC ANALYSIS; CONTROLLED STUDY; CRYSTALLIZATION; DISPERSION; DRUG SOLUBILITY; DRUG STRUCTURE; KINETICS; MICROSCOPY; PHASE TRANSITION; RAMAN SPECTROMETRY; ANALOGS AND DERIVATIVES; CHEMISTRY; SOLUBILITY;

CRYSTALLIZATION; HYPROMELLOSE DERIVATIVES; KINETICS; NIFEDIPINE; PHASE TRANSITION; POLYMERS; POVIDONE; SOLUBILITY; SPECTRUM ANALYSIS, RAMAN;

EID: 84908007389     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500333v     Document Type: Article

References (64)

1. Serajuddin, A. T. M. Solid dispersion of poorly water-soluble drugs: Early promises, subsequent problems, and recent breakthroughs J. Pharm. Sci. 1999, 88 (10) 1058-1066
2. Leuner, C.; Dressman, J. Improving drug solubility for oral delivery using solid dispersions Eur. J. Pharm. Biopharm. 2000, 50 (1) 47-60
3. 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 (1) 171-184
4. Taylor, L. S.; Zografi, G. Spectroscopic Characterization of Interactions Between PVP and Indomethacin in Amorphous Molecular Dispersions Pharm. Res. 1997, 14 (12) 1691-1698
5. Matsumoto, T.; Zografi, G. Physical Properties of Solid Molecular Dispersions of Indomethacin with Polyvinylpyrrolidone and Polyvinylpyrrolidone-co-vinyl-acetate in Relation to Indomethacin Crystallization Pharm. Res. 1999, 16 (11) 1722-1728
6. Tang, X. C.; Pikal, M. J.; Taylor, L. S. A Spectroscopic Investigation of Hydrogen Bond Patterns in Crystalline and Amorphous Phases in Dihydropyridine Calcium Channel Blockers Pharm. Res. 2002, 19 (4) 477-483
7. 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
8. 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 (11) 2710-2717
9. Marsac, P.; Konno, H.; Rumondor, A.; Taylor, L. Recrystallization of Nifedipine and Felodipine from Amorphous Molecular Level Solid Dispersions Containing Poly(vinylpyrrolidone) and Sorbed Water Pharm. Res. 2008, 25 (3) 647-656
10. Marsac, P.; Konno, H.; Taylor, L. A Comparison of the Physical Stability of Amorphous Felodipine and Nifedipine Systems Pharm. Res. 2006, 23 (10) 2306-2316
11. Alonzo, D.; Zhang, G. Z.; Zhou, D.; Gao, Y.; Taylor, L. Understanding the Behavior of Amorphous Pharmaceutical Systems during Dissolution Pharm. Res. 2010, 27 (4) 608-618
12. 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
13. Mullin, J. W. Crystallization, 4 th ed.; Butterworth-Heinemann: Woburn, MA, 2001.
14. Abbou Oucherif, K.; Raina, S.; Taylor, L. S.; Litster, J. D. Quantitative analysis of the inhibitory effect of HPMC on felodipine crystallization kinetics using population balance modeling CrystEngComm 2013, 15 (12) 2197-2205
15. 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
16. Eerdenbrugh, B.; Raina, S.; Hsieh, Y.-L.; Augustijns, P.; Taylor, L. Classification of the Crystallization Behavior of Amorphous Active Pharmaceutical Ingredients in Aqueous Environments Pharm. Res. 2013, 1-14
17. Raina, S. A.; Zhang, G. G. Z.; Alonzo, D. E.; Wu, J.; Zhu, D.; Catron, N. D.; Gao, Y.; Taylor, L. S. Enhancements and Limits in Drug Membrane Transport Using Supersaturated Solutions of Poorly Water-Soluble Drugs J. Pharm. Sci. 2013, n/a-n/a
18. 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
19. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Inhibition of solution crystal growth of ritonavir by cellulose polymers-factors influencing polymer effectiveness CrystEngComm 2012, 14 (20) 6503-6514
20. Sarode, A. L.; Sandhu, H.; Shah, N.; Malick, W.; Zia, H. Hot melt extrusion (HME) for amorphous solid dispersions: Predictive tools for processing and impact of drug-polymer interactions on supersaturation Eur. J. Pharm. Sci. 2013, 48 (3) 371-384
21. Raghavan, S. L.; Kiepfer, B.; Davis, A. F.; Kazarian, S. G.; Hadgraft, J. Membrane transport of hydrocortisone acetate from supersaturated solutions; the role of polymers Int. J. Pharm. 2001, 221 (1-2) 95-105
22. Threlfall, T. Structural and Thermodynamic Explanations of Ostwald's Rule Org. Process Res. Dev 2003, 7 (6) 1017-1027
23. Grzesiak, A. L.; Matzger, A. J. Selection of Protein Crystal Forms Facilitated by Polymer-Induced Heteronucleation Cryst. Growth Des. 2007, 8 (1) 347-350
24. Price, C. P.; Grzesiak, A. L.; Matzger, A. J. Crystalline Polymorph Selection and Discovery with Polymer Heteronuclei J. Am. Chem. Soc. 2005, 127 (15) 5512-5517
25. Lang, M.; Grzesiak, A. L.; Matzger, A. J. The Use of Polymer Heteronuclei for Crystalline Polymorph Selection J. Am. Chem. Soc. 2002, 124 (50) 14834-14835
26. Gift, A. D.; Luner, P. E.; Luedeman, L.; Taylor, L. S. Influence of polymeric excipients on crystal hydrate formation kinetics in aqueous slurries J. Pharm. Sci. 2008, 97 (12) 5198-5211
27. Giron, D. Investigations of Polymorphism and Pseudo-polymorphism in Pharmaceuticals by Combined Thermoanalytical Techniques J. Therm. Anal. Calorim. 2001, 64 (1) 37-60
28. Haleblian, J. K. Characterization of habits and crystalline modification of solids and their pharmaceutical applications J. Pharm. Sci. 1975, 64 (8) 1269-1288
29. Khalil, S. A.; Moustafa, M. A.; Ebian, A. R.; Motawi, M. M. GI absorption of two crystal forms of sulfameter in man J. Pharm. Sci. 1972, 61 (10) 1615-1617
30. M. W. Kunst, H. Mu. Absorption of Pivampicillin in Postoperative Patients Antimicrob. Agents Chemother. 1975, 8 (1) 11-14
31. 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) 3787-3806
32. Gnutzmann, T.; Kahlau, R.; Scheifler, S.; Friedrichs, F.; Rossler, E. A.; Rademann, K.; Emmerling, F. Crystal growth rates and molecular dynamics of nifedipine CrystEngComm 2013, 15 (20) 4062-4069
33. Gunn, E.; Guzei, I. A.; Cai, T.; Yu, L. Polymorphism of Nifedipine: Crystal Structure and Reversible Transition of the Metastable β Polymorph Cryst. Growth Des. 2012, 12 (4) 2037-2043
34. Klimakow, M.; Rademann, K.; Emmerling, F. Toward Novel Pseudo-Polymorphs of Nifedipine: Elucidation of a Slow Crystallization Process Cryst. Growth Des. 2010, 10 (6) 2693-2698
35. Grooff, D.; Liebenberg, W.; De Villiers, M. M. Preparation and transformation of true nifedipine polymorphs: Investigated with differential scanning calorimetry and X-Ray diffraction pattern fitting methods J. Pharm. Sci. 2011, 100 (5) 1944-1957
36. Chan, K. L. A.; Fleming, O. S.; Kazarian, S. G.; Vassou, D.; Chryssikos, G. D.; Gionis, V. Polymorphism and devitrification of nifedipine under controlled humidity: a combined FT-Raman, IR and Raman microscopic investigation J. Raman Spectrosc. 2004, 35 (5) 353-359
37. Braun, D. E.; Maas, S. G.; Zencirci, N.; Langes, C.; Urbanetz, N. A.; Griesser, U. J. Simultaneous quantitative analysis of ternary mixtures of d-mannitol polymorphs by FT-Raman spectroscopy and multivariate calibration models Int. J. Pharm. 2010, 385 (1-2) 29-36
38. Blanco, M.; Alcalá, M.; González, J. M.; Torras, E. Near infrared spectroscopy in the study of polymorphic transformations Anal. Chim. Acta 2006, 567 (2) 262-268
39. Xie, Y.; Cao, W.; Krishnan, S.; Lin, H.; Cauchon, N. Characterization of Mannitol Polymorphic Forms in Lyophilized Protein Formulations Using a Multivariate Curve Resolution (MCR)-Based Raman Spectroscopic Method Pharm. Res. 2008, 25 (10) 2292-2301
40. Shamsipur, M.; Hemmateenejad, B.; Akhond, M.; Javidnia, K.; Miri, R. A study of the photo-degradation kinetics of nifedipine by multivariate curve resolution analysis J. Pharm. Biomed. 2003, 31 (5) 1013-1019
41. Christensen, N. P.; Van Eerdenbrugh, B.; Kwok, K.; Taylor, L. S.; Bond, A. D.; Rades, T.; Rantanen, J.; Cornett, C. Rapid Insight into Heating-Induced Phase Transformations in the Solid State of the Calcium Salt of Atorvastatin Using Multivariate Data Analysis Pharm. Res. 2013, 30 (3) 826-835
42. Li, B.; Konecke, S.; Harich, K.; Wegiel, L.; Taylor, L. S.; Edgar, K. J. Solid dispersion of quercetin in cellulose derivative matrices influences both solubility and stability Carbohydr. Polym. 2013, 92 (2) 2033-2040
43. Bhugra, C.; Pikal, M. J. Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state J. Pharm. Sci. 2008, 97 (4) 1329-1349
44. Van Eerdenbrugh, B.; Baird, J. A.; Taylor, L. S. Crystallization tendency of active pharmaceutical ingredients following rapid solvent evaporation-classification and comparison with crystallization tendency from undercooled melts J. Pharm. Sci. 2010, 99 (9) 3826-38
45. Kestur, U. S.; Taylor, L. S. Role of polymer chemistry in influencing crystal growth rates from amorphous felodipine CrystEngComm 2010, 12 (8) 2390-2397
46. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Understanding Polymer Properties Important for Crystal Growth Inhibition-Impact of Chemically Diverse Polymers on Solution Crystal Growth of Ritonavir Cryst. Growth Des. 2012, 12 (6) 3133-3143
47. Zhou, D.; Schmitt, E. A.; Zhang, G. G.; Law, D.; Vyazovkin, S.; Wight, C. A.; Grant, D. J. W. Crystallization kinetics of amorphous nifedipine studied by model-fitting and model-free approaches J. Pharm. Sci. 2003, 92 (9) 1779-1792
48. Keymolen, B.; Ford, J. L.; Powell, M. W.; Rajabi-Siahboomi, A. R. Investigation of the polymorphic transformations from glassy nifedipine Thermochim. Acta 2003, 397, 103
49. Ishida, H.; Wu, T.; Yu, L. Sudden rise of crystal growth rate of nifedipine near Tg without and with polyvinylpyrrolidone J. Pharm. Sci. 2007, 96 (5) 1131-1138
50. Burger, A.; Koller, A. T. Polymorphism and pseudopolymorphism on Nifedipine Sci. Pharm. 1996, 64, 293
51. Grooff, D.; De Villiers, M. M.; Liebenberg, W. Thermal methods for evaluating polymorphic transitions in nifedipine Thermochim. Acta 2007, 454 (1) 33-42
52. Caira, M. R.; Robbertse, Y.; Bergh, J. J.; Song, M.; De Villiers, M. M. Structural characterization, physicochemical properties, and thermal stability of three crystal forms of nifedipine J. Pharm. Sci. 2003, 92 (12) 2519-2533
53. Aso, Y.; Yoshioka, S.; Kojima, S. Feasibility of using isothermal microcalorimetry to evaluate the physical stability of amorphous nifedipine and phenobarbital Thermochim. Acta 2001, 380 (2) 199-204
54. Otsuka, M.; Kato, F.; Matsuda, Y. Physicochemical stability of cimetidine amorphous forms estimated by isothermal microcalorimetry AAPS PharmSciTech 2002, 3 (4) 32-44
55. Chan, K. L. A.; Kazarian, S. G.; Vassou, D.; Gionis, V.; Chryssikos, G. D. In situ high-throughput study of drug polymorphism under controlled temperature and humidity using FT-IR spectroscopic imaging Vib. Spectrosc. 2007, 43 (1) 221-226
56. Xu, A.-W.; Dong, W.-F.; Antonietti, M.; Cölfen, H. Polymorph Switching of Calcium Carbonate Crystals by Polymer-Controlled Crystallization Adv. Funct. Mater. 2008, 18 (8) 1307-1313
57. Raghavan, S. L.; Trividic, A.; Davis, A. F.; Hadgraft, J. Crystallization of hydrocortisone acetate: influence of polymers Int. J. Pharm. 2001, 212 (2) 213-221
58. Amjad, Z.; Pugh, J.; Reddy, M., Kinetic Inhibition of Calcium Carbonate Crystal Growth in the Presence of Natural and Synthetic Organic Inhibitors. In Water Soluble Polymers; Amjad, Z., Ed.; Springer: New York, 2002; pp 131-147.
59. Ilevbare, G. A.; Liu, H.; Pereira, J.; Edgar, K. J.; Taylor, L. S. Influence of Additives on the Properties of Nanodroplets Formed in Highly Supersaturated Aqueous Solutions of Ritonavir Mol. Pharmaceutics 2013, 10 (9) 3392-3403
60. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Impact of Polymers on Crystal Growth Rate of Structurally Diverse Compounds from Aqueous Solution Mol. Pharmaceutics 2013, 10 (6) 2381-2393
61. Wikström, H.; Rantanen, J.; Gift, A. D.; Taylor, L. S. Toward an Understanding of the Factors Influencing Anhydrate-to-Hydrate Transformation Kinetics in Aqueous Environments Cryst. Growth Des. 2008, 8 (8) 2684-2693
62. Qiu, Y.; Chen, Y.; Zhang, G. G. Z.; Liu, L.; Porter, W. R., Eds. Developing Solid Oral Dosage Forms: Pharmaceutical Theory & Practice; Elsevier: New York, 2009.
63. Pudipeddi, M.; Serajuddin, A. T. M. Trends in solubility of polymorphs J. Pharm. Sci. 2005, 94 (5) 929-939
64. Aguiar, A. J.; Zelmer, J. E. Dissolution behavior of polymorphs of chloramphenicol palmitate and mefenamic acid J. Pharm. Sci. 1969, 58 (8) 983-987