Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine

Journal of Pharmaceutical Sciences

Volumn 95, Issue 12, 2006, Pages 2692-2705

  Konno, Hajime ^a,b   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

Amorphous; Calorimetry (DSC); Crystallization; FTIR; Solid dispersion

Indexed keywords

FELODIPINE; HYDROXYPROPYLMETHYLCELLULOSE; HYDROXYPROPYLMETHYLCELLULOSE ACETATE SUCCINATE; POLYMER; POVIDONE;

ARTICLE; CRYSTALLIZATION; DISPERSION; DRUG COATING; DRUG MANUFACTURE; DRUG MIXTURE; ENTHALPY; EVAPORATION; GLASS TRANSITION TEMPERATURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; MOLECULAR MECHANICS; SOLID STATE; THERMAL ANALYSIS;

EID: 33846256269     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20697     Document Type: Article

References (46)

1. Sekiguchi K, Obi N. 1961. Studies on absorption of eutectic mixture 1. A comparison of the behavior of eutectic mixture of sulphathiazole and that of ordinary sulfathiazole in man. Chem Pharm Bull 9:866-872.
2. Chiou WL, Riegelman S. 1971. Pharmaceutical applications of solid dispersions. J Pharm Sci 60: 1281-1302.
3. Ford JL. 1986. The current status of solid dispersions. Pharm Acta Helv 61:69-88.
4. Serajuddin ATM. 1999. Solid dispersions of poorly water-soluble drugs: Early promises, subsequent problems and recent breakthroughs. J Pharm Sci 88:1058-1066.
5. Leuner C, Dressman J. 2000. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50:47-60.
6. Simonelli AP, Mehta SC, Higuchi WI. 1970. Inhibition of sulfathiazole crystal growth by PVP. J Pharm Sci 59:633-637.
7. Yoshioka M, Hancock BC, Zografi G. 1995. Inhibition of indomethacin crystallization in poly(vinylpyrrolidone). J Pharm Sci 84:983-986.
8. Taylor LS, Zografi G. 1997. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res 14:1691-1698.
9. Choiu WL, Riegelman S. 1969. Preparation and dissolution characteristics of several-fast release solid dispersions of griseofluvin. J Pharm Sci 58: 1505-1509.
10. Lin CW, Cham TM. 1996. Effect of particle size on the available surface area of nifedipine from nifedipine-poly(ethylene glycol) 6000 solid dispersions. Int J Pharm 127:261-272.
11. Mura P, Manderioli A, Bramanti G, Ceccarelli L. 1996. Properties of solid dispersion of naproxen in various poly(ethylene glycol)s. Drug Dev Ind Pharm 22:909-916.
12. Hino T, Ford JL. 2001. Characterization of the hydroxypropylmethylcellulose-nicontinamide binary system. Int J Pharm 219:39-49.
13. Yamashita K, Nakate T, Okimoto K, Ohike A, Tokunaga Y, Ibuki R, Higaki K, Kimura T. 2003. Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int J Pharm 267:79-91.
14. Jolley JE. 1970. Microstructure of photographic gelatin binders. Photogr Sci Eng 14:169-177.
15. Van den Mooter G, Wuyts M, Blaton N, Busson R, Grobet P, Augustijns P, Kinget R. 2001. Physical stabilisation of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25. Eur J Pharm Sci 12:261-269.
16. Oksanen CA, Zografi G. 1990. The relationship between the glass transition temperature and water vapor absorption by poly(vinylpyrrolidone). Pharm Res 7:654-657.
17. Abe Y, Arahori T, Naruse A. 1976. Crystallization of calcium metaphosphate glass below the glass transition temperature. A J Am Ceram Soc 59:487-490.
18. Yoshioka M, Hancock BC, Zografi G. 1994. Crystallization of indomethacin from the amorphous state below and above its glass transition temperature. J Pharm Sci 83:1700-1705.
19. Taylor LS, Zografi G. 1997. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res 14:1691-1698.
20. Tang XC, Pikal MJ, Taylor LS. 2002. A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers. Pharm Res 19:477-483.
21. Miyazaki T, Yoshioka S, Aso Y, Kojima S. 2004. Ability of polyvinylpyrrolidone and polyacrylic acid to inhibit the crystallization of amorphous acetaminophen. J Pham Sci 93:2710-2717.
22. Andronis V, Zografi G. 2000. Crystal nucleation and growth of indomethacin polymorphs from the amorphous state. J Non-Cryst Sol 271:236-248.
23. Inoue S, Oldenbourg R. 1995. Microscopes. In: Bass M, editor. Handbook of optics, Vol. 2. New York: McGraw-Hill.
24. Gordon M, Taylor JS. 1952. Ideal co-polymers and the second-order transitions of synthetic rubbers. J Appl Chem 2:493-500.
25. Simha R, Boyer RF. 1962. On a general relation involving the glass temperature and coefficients of expansion of polymers. J Chem Phys 37:1003-1007.
26. Couchman PR, Karasz FE. 1978. A classical thermodynamic discussion on the effect of composition on glass-transition temperatures. Macromolecules 11:117-119.
27. Hancock BC, Shamblin SL, Zografi G. 1995. Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures. Pharm Res 12:799-806.
28. Shamblin SL, Zografi G. 1998. Enthalpy relaxation in binary amorphous mixtures containing sucrose. Pharm Res 15:1828-1834.
29. Nitta K, Shin Y, Hashiguchi H, Tanimoto S, Terano M. 2005. Morphology and mechanical properties in the binary blends of isotactic polypropylene and novel propylene-co-olefin random copolymers with isotactic propylene sequence 1. Ethylene-propylene copolymers. Polymer 46:965-975.
30. Shamblin SL, Taylor LS, Zografi G. 1998. Mixing behavior of colyophilized binary systems. J Pharm Sci 87:694-701.
31. 2+ antagonist felodipine. Dihydropyridine binding prerequisites assessed from crystallographic data. J Med Chem 29:305-307.
32. Jeffrey GA. 1997. An introduction to hydrogen bonding. New York: Oxford University Press.
33. Matsumoto T, Zografi G. 1999. Physical properties of solid dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinyl acetate) in relation to indomethacin crystallization. Pharm Res 16:1722-1728.
34. Khougaz K, Clas SD. 2000. Crystallization inhibition in solid dispersions of MK-0591 and poly(vinylpyrrolidone) polymers. J Pharm Sci 89: 1325-1334.
35. Coleman MM, Graf JF, Painter P. 1991. Specific interactions and the miscibility of polymer blends. Lancaster: Technomic Publishing Company, Inc.
36. Aso Y, Yoshioka S, Chang J, Zografi G. 2002. Effect of water on the molecular mobility of sucrose and poly(vinylpyrrolidone) in a colyophilized formulation as measured by C-13-NMR relaxation time. Chem Pharm Bull 50:822-826.
37. Fujii M, Hasegawa J, Kitajima H, Matsumoto M. 1991. The solid dispersion of benzodiazepins with phosphatidylcholine-the effect of substituents of benzodiazepins on the formation of solid dispersions. Chem Pharm Bull 39:3013-3017.
38. Brekner MJ, Schneider HA, Cantow HJ. 1988. Approach to the composition dependence of the glass transition temperature of compatible polymer blends: 1. Polymer 29:78-85.
39. Turnbull D, Fisher JC. 1949. Rate of nucleation in condensed systems. J Chem Phys 17:71-73.
40. Angell CA. Origin and control of low-melting behavior in salts, polysalts, salt solvates, and glass formers. In: Gaune-Escard, editor. 2002. Molten salts: From fundamentals to applications. The Netherlands: Kluwer Academic Publishers, pp 305-322.
41. Flory PJ. 1953. Principles of polymer chemistry. Ithaca, New York: Cornell University.
42. Hancock BC, Zografi G. 1993. 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 10:1262-1267.
43. Zhang J, Zografi G. 2001. Water vapor absorption into amorphous sucrose-poly(vinylpyrrolidone) and trehalose-poly(vinylpyrrolidone) mixtures. J Pharm Sci 90:1375-1385.
44. Chang LQ, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ. 2005. Mechanism of protein stabilization by sugars during freeze-drying and storage: Native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci 94:1427-1444.
45. Stein RS. 1994. Crystallization from polymer blends. Materials Research Society Symposium Proceedings 321 (Crystallization and Related Phenomena in Amorphous Materials), pp 531-542.
46. Crowley KJ, Zografi G. 2003. The effect of low concentrations of molecularly dispersed poly(vinylpyrrolidone) on indomethacin crystallization from the amorphous state. Pharm Res 20:1417-1422.