Inhibition of crystal nucleation and growth by water-soluble polymers and its impact on the supersaturation profiles of amorphous drugs

Journal of Pharmaceutical Sciences

Volumn 102, Issue 7, 2013, Pages 2273-2281

  Ozaki, Shunsuke ^a,b   Kushida, Ikuo ^a   Yamashita, Taro ^a   Hasebe, Takashi ^a   Shirai, Osamu ^b   Kano, Kenji ^b  

^a EISAI CO LTD   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Amorphous; Crystal growth; Crystal nucleation; Crystallization; Kinetics; Polymers; Supersaturation

Indexed keywords

DANAZOL; EUDRAGIT; GRISEOFULVIN; HYDROXYPROPYLMETHYLCELLULOSE; POLYMER; POVIDONE; WATER;

ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG FORMULATION; DRUG SOLUBILITY; QUALITY CONTROL;

EID: 84879009647     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23588     Document Type: Article

References (32)

1. Sugano K. 2009. Introduction to computational oral absorption simulation. Expert Opin Drug Metab Toxicol 5:252-293.
2. Sugano K. 2009. A simulation of oral absorption using classical nucleation theory. Int J Pharm 378:142-145.
3. Brouwers J, Brewster ME, Augustijns P. 2009. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J Pharm Sci 98:2549-2572.
4. Carlert S, Pålsson A, Hanisch G, Corswant C, Nilsson C, Lindfors L, Lennernäs H, Abrahamsson B. 2010. Predicting intestinal precipitation-A case example for a basic BCS class II drug. Phram Res 27:2119-2130.
5. Takano R, Takata N, Saito R, Furumoto K, Higo S, Hayashi Y, Machida M, Aso Y, Yamashita S. 2010. Quantitative analysis of the effect of supersaturation on in vivo drug absorption. Mol Pharm 7:1431-1440.
6. Hancock BC, Parks M. 2000. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res 17:397-404.
7. Matteucci ME, Miller MA, Williams III RO, Johnston KP. 2008. Highly supersaturated solutions of amorphous drugs approaching predictions from configurational thermodynamic properties. J Phys Chem B 112:16675-16681.
8. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. 2010. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J Pharm Sci 99:1254-1264.
9. Vaughn JM, McConville JT, Crisp MT, Johnston KP, Williams III RO. 2006. Supersaturation produces high bioavailability of amorphous danazol particles formed by evaporative precipitation into aqueous solution and spray freezing into liquid technologies. Drug Dev Ind Pharm 32:559-567.
10. Zhang S, Kawakami K, Yamamoto M, Masaoka Y, Kataoka M, Yamashita S, Sakuma S. 2011. Coaxial electrospray formulations for improving oral absorption of a poorly water-soluble drug. Mol Pharm 8:807-813.
11. Kushida I, Ichikawa M, Asakawa N. 2002. Improvement of dissolution and oral absorption of ER-34122, a poorly water-soluble dual 5-lipoxygenase/cyclooxygenase inhibitor with anti-inflammatory activity by preparing solid dispersion. J Pharm Sci 91:258-266.
12. Kawakami K. 2009. Current status of amorphous formulation and other special dosage forms as formulations for early clinical phases. J Pharm Sci 98:2875-2885.
13. Ozaki S, Kushida I, Yamashita T, Hasebe T, Shirai O, Kano K. 2012. Evaluation of drug supersaturation by thermodynamic and kinetic approaches for the prediction of oral absorbability in amorphous pharmaceuticals. J Pharm Sci 101:4220-4230.
14. Murdande SB, Ikal MJ, Shanker RM, Bogner RH. 2011. Solubility advantage of amorphous pharmaceuticals: III. Is maximum solubility advantage experimentally attainable and sustainable? J Pharm Sci 100:4349-4356.
15. Guzman HR, Tawa M, Zhang Z, Ratanabanangkoon P, Shaw P, Gardner CR, Chen H, Moreau JP, Almarsson O, Remenar JF. 2007. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J Pharm Sci 96:2686-2702.
16. Yamashita T, Ozaki S, Kushida I. 2011. Solvent shift method for anti-precipitant screening of poorly soluble drugs using biorelevant medium and dimethyl sulfoxide. Int J Pharm 419:170-174.
17. Lindfors L, Forssén S, Westergren J, Olsson U. 2008. Nucleation and crystal growth in supersaturated solutions of a model drug. J Colloid Interface Sci 325:404-413.
18. Alonzo DE, Raina S, Zhou D, Gao Y, Zhang GGZ, Taylor LS. 2012. Characterizing the impact of hydroxypropylmethyl cellulose on the growth and nucleation kinetics of felodipine from supersaturated solutions. Cryst Growth Des 12:1538-1547.
19. Ozaki S, Minamisono T, Yamashita T, Kato T, Kushida I. 2012. Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms. J Pharm Sci 101:214-222.
20. Takano R, Sugano K, Higashida A, Hayashi Y, Machida M, Aso Y, Yamashita S. 2006. Oral absorption of poorly water-soluble drugs: Computer simulation of fraction absorbed in humans from a miniscale dissolution test. Pharm Res 23:1144-1156.
21. Gu CH, Young Jr V, Grant DJW. 2001. Polymorph screening: Influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci 90:1878-1890.
22. Kuldipkumar A, Kwon GS, Zhang GGZ. 2007. Determining the growth mechanism of tolazamide by induction time measurement. Cryst Growth Des 7:234-242.
23. Dressman JB, Reppas C. 2000. In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs. Eur J Pharm 11:S73-S80.
24. Miller JM, Beig A, Carr RA, Webster GK, Dahan A. 2012. The solubility-permeability interplay when using cosolvents for solubilization: Revising the way we use solubility-enabling formulations. Mol Pharm 9:581-590.
25. DiNunzio JC, Miller DA, Yang W, McGinity JW, Williams III RO. 2008. Amorphous compositions using concentration enhancing polymers for improved bioavailability of itraconazole. Mol Pham 5:968-960.
26. Taylor LS, Zografi G. 1997. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res 14:1691-1698.
27. Kushida I, Gotoda M. 2012. Investigation for the amorphous state of ER-34122, a dual 5-lipoxygenase/cyclooxygenase inhibitor with poor aqueous solubility, in HPMC solid dispersion prepared by the solvent evaporation method. Drug Dev Ind Pharm. [Epub ahead of print.] DOI:10.3109/03639045.2012.679279.
28. Konno H, Taylor LS. 2006. Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine. J Pharm Sci 95:2692-2705.
29. Konno H, Taylor LS. 2008. Ability of different polymers to inhibit the crystallization of amorphous felodipine in the presence of moisture. Pharm Res 25:969-978.
30. Raghavan SL, Trividic A, Davis AF, Hadgraft J. 2001. Crystallization of hydrocortisone acetate: Influence of polymers. Int J Pharm 212:213-221.
31. Ilevbare GA, Liu H, Edgar KJ, Taylor LS. 2012. Inhibition of solution crystal growth of ritonavir by cellulose polymers-Factors influencing polymer effectiveness. Cryst Eng Comm 14:6503-6514.
32. Ilevbare GA, Liu H, Edgar KJ, Taylor LS. 2013. Maintaining supersaturation in aqueous drug solutions: Impact of different polymers on induction times. Cryst Growth Des 13:740-751.