Crystallization of Amorphous Solid Dispersions of Resveratrol during Preparation and Storage—Impact of Different Polymers

Lindsay A. Wegiel; Lisa J. Mauer; Kevin J. Edgar; Lynne S. Taylor

doi:10.1002/jps.23358

journal article Jan 01, 2013

Crystallization of Amorphous Solid Dispersions of Resveratrol during Preparation and Storage—Impact of Different Polymers

Lindsay A. Wegiel Lisa J. Mauer Kevin J. Edgar Lynne S. Taylor

Journal of Pharmaceutical Sciences Vol. 102 No. 1 pp. 171-184 · Elsevier BV

View at Publisher Save 10.1002/jps.23358

Topics

No keywords indexed for this article. Browse by subject →

References

39

[1]

Leuner "Improving drug solubility for oral delivery using solid dispersions" Eur J Pharm Biopharm (2000) 10.1016/s0939-6411(00)00076-x

[2]

"Solid dispersion of poorly water‐soluble drugs: Early promises, subsequent problems, and recent breakthroughs" J Pharm Sci (1999) 10.1021/js980403l

[3]

Chiou "Pharmaceutical applications of solid dispersion systems" J Pharm Sci (1971) 10.1002/jps.2600600902

[4]

Andronis "Crystal nucleation and growth of indomethacin polymorphs from the amorphous state" J Non‐Cryst Solids (2000) 10.1016/s0022-3093(00)00107-1

[5]

Gupta "Stability and solubility of celecoxib–PVP amorphous dispersions: A molecular perspective" Pharm Res (2004) 10.1023/b:pham.0000045226.42859.b8

[6]

Oberholtzer "Cefoxitin sodium: Solution and solid‐state chemical stability studies" J Pharm Sci (1979) 10.1002/jps.2600680720

[7]

Pikal "Quantitative crystallinity determinations for Î2‐lactam antibiotics by solution calorimetry: Correlations with stability" J Pharm Sci (1978) 10.1002/jps.2600670609

[8]

Rumondor "Effects of polymer type and storage relative humidity on the kinetics of felodipine crystallization from amorphous solid dispersions" Pharm Res (2009) 10.1007/s11095-009-9974-3

[9]

Characteristics and Significance of the Amorphous State in Pharmaceutical Systems

Bruno C. Hancock, George Zografi

Journal of Pharmaceutical Sciences 1997 10.1021/js9601896

[10]

Ford "The current status of solid dispersions" Pharm Acta Helv (1986)

[11]

Khougaz "Crystallization inhibition in solid dispersions of MK‐0591 and poly(vinylpyrrolidone) polymers" J Pharm Sci (2000) 10.1002/1520-6017(200010)89:10<1325::aid-jps10>3.0.co;2-5

[12]

Taylor "Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions" Pharm Res (1997) 10.1023/a:1012167410376

[13]

Van den Mooter "Physical stabilization of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25" Eur J Pharm Sci (2001) 10.1016/s0928-0987(00)00173-1

[14]

Matsumoto "Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone‐co‐vinyl‐acetate) in relation to indomethacin crystallization" Pharm Res (1999) 10.1023/a:1018906132279

[15]

Taylor "Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions" Pharm Res (1997) 10.1023/a:1012167410376

[16]

Matsumoto "Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone‐co‐vinylacetate) in relation to indomethacin crystallization" Pharm Res (1999) 10.1023/a:1018906132279

[17]

Miyazaki "Ability of polyvinylpyrrolidone and polyacrylic acid to inhibit the crystallization of amorphous acetaminophen" J Pharm Sci (2004) 10.1002/jps.20182

[18]

Khougaz "Crystallization inhibition in solid dispersions of MK‐0591 and poly(vinylpyrrolidone) polymers" J Pharm Sci (2000) 10.1002/1520-6017(200010)89:10<1325::aid-jps10>3.0.co;2-5

[19]

Tong "A study of amorphous molecular dispersions of indomethacin and its sodium salt" J Pharm Sci (2001) 10.1002/jps.1150

[20]

Tang "A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers" Pharm Res (2002) 10.1023/a:1015147729564

[21]

Kestur "Role of polymer chemistry in influencing crystal growth rates from amorphous felodipine" CrystEngComm (2010) 10.1039/c001905d

[22]

Van Eerdenbrugh "Small scale screening to determine the ability of different polymers to inhibit drug crystallization upon rapid solvent evaporation" Mol Pharm (2010) 10.1021/mp1001153

[23]

Van Eerdenbrugh "An ab initio polymer selection methodology to prevent crystallization in amorphous solid dispersions by application of crystal engineering principles" CrystEngComm (2011) 10.1039/c1ce05183k

[24]

Baur "Resveratrol, sirtuins, and the promise of a DR mimetic" Mech Ageing Dev (2010) 10.1016/j.mad.2010.02.007

[25]

Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan

Konrad T. Howitz, Kevin J. Bitterman, Haim Y. Cohen et al.

Nature 2003 10.1038/nature01960

[26]

Sun "Measurement and correlation of solubility of trans‐resveratrol in 11 solvents at T = (278.2, 288.2, 298.2, 308.2, and 318.2) K" J Chem Thermodyn (2008) 10.1016/j.jct.2007.10.006

[27]

Van Eerdenbrugh "Crystallization tendency of active pharmaceutical ingredients following rapid solvent evaporation-classification and comparison with crystallization tendency from undercooled melts" J Pharm Sci (2010) 10.1002/jps.22214

[28]

Jeffrey (1997)

[29]

Marsac "A comparison of the physical stability of amorphous felodipine and nifedipine systems" Pharm Res (2006) 10.1007/s11095-006-9047-9

[30]

Moustafine "Physicochemical characterization and drug release properties of Eudragit E PO/Eudragit L 100‐55 interpolyelectrolyte complexes" Eur J Pharm Biopharm (2006) 10.1016/j.ejpb.2005.10.005

[31]

Caruso "Structural basis for antioxidant activity of trans‐resveratrol: Ab initio calculations and crystal and molecular structure" J Agric Food Chem (2004) 10.1021/jf048794e

[32]

Saenger "Flip‐flop hydrogen bonding in a partially disordered system" Nature (London) (1982) 10.1038/296581a0

[33]

Saenger "Flip‐flop hydrogen bridging bonds in Î2‐cyclodextrin—A general principle in polysaccharides" Angew Chem (1983) 10.1002/ange.19830951124

[34]

Etter "Encoding and decoding hydrogen‐bond patterns of organic compounds" Acc Chem Res (1990) 10.1021/ar00172a005

[35]

Etter "Hydrogen bonds as design elements in organic chemistry" J Phys Chem (1991) 10.1021/j100165a007

[36]

Laurence "The pKBHX database: Toward a better understanding of hydrogen‐bond basicity for medicinal chemists" J Med Chem (2009) 10.1021/jm801331y

[37]

Taylor "Fourier transform Raman spectroscopic study of the interaction of water vapor with amorphous polymers" J Pharm Sci (2001) 10.1002/jps.1041

[38]

Rumondor ACF, Konno H, Marsac PJ, Taylor LS. Analysis of the moisture sorption behavior of amorphous drug-polymer blends. J Appl Polym Sci 117(2):1055–1063. 10.1002/app.31803

[39]

Rumondor "Understanding the tendency of amorphous solid dispersions to undergo amorphous‐amorphous phase separation in the presence of absorbed moisture" AAPS PharmSciTech (2011) 10.1208/s12249-011-9686-y

Cited By

180

Amorphous solid dispersion preparation via coprecipitation improves the dissolution, oral bioavailability, and intestinal health enhancement properties of magnolol

Jia Cao, Shixia Zhang · 2023

Poultry Science

Potential Therapeutic Targets of Resveratrol in the Prevention and Treatment of Pulmonary Fibrosis

Iman Ramli, Thamere Cheriet · 2023

Frontiers in Bioscience-Landmark

Precise Dosing of Pramipexole for Low-Dosed Filament Production by Hot Melt Extrusion Applying Various Feeding Methods

Rebecca Chamberlain, Hellen Windolf · 2022

Pharmaceutics

Metrics

180

Citations

39

References

Details

Published: Jan 01, 2013
Vol/Issue: 102(1)
Pages: 171-184
License: View

Authors

Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, Virginia 24061, United States

L

Lynne S. Taylor

Department of Industrial and Physical Pharmacy, College of Pharmacy, Purdue University, West Lafayette, Indiana 47907, United States

Cite This Article

Lindsay A. Wegiel, Lisa J. Mauer, Kevin J. Edgar, et al. (2013). Crystallization of Amorphous Solid Dispersions of Resveratrol during Preparation and Storage—Impact of Different Polymers. Journal of Pharmaceutical Sciences, 102(1), 171-184. https://doi.org/10.1002/jps.23358

Crystallization of Amorphous Solid Dispersions of Resveratrol during Preparation and Storage—Impact of Different Polymers

You May Also Like