Implications of Drug–Polymer Interactions on Time–Temperature–Transformation: A Tool to Assess the Crystallization Propensity in Amorphous Solid Dispersions

Lalge, Rahul; Kumar, N. S.  Krishna; Suryanarayanan, Raj

doi:10.1021/acs.molpharmaceut.2c01004

Implications of Drug–Polymer Interactions on Time–Temperature–Transformation: A Tool to Assess the Crystallization Propensity in Amorphous Solid Dispersions

Journal Article · 05 February 2023 · Molecular Pharmaceutics

DOI:https://doi.org/10.1021/acs.molpharmaceut.2c01004· OSTI ID:2423471

^[1]; Kumar, N. S. Krishna ^[1]; ^[1]

Department of Pharmaceutics, College of Pharmacy, University of Minnesota, 9-177 WDH, 308 Harvard Street S.E., Minneapolis, Minnesota55455, United States

Not provided.

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 2423471

Journal Information:: Molecular Pharmaceutics, Journal Name: Molecular Pharmaceutics Journal Issue: 3 Vol. 20; ISSN 1543-8384

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (55)

Amino acids as co-amorphous stabilizers for poorly water soluble drugs – Part 1: Preparation, stability and dissolution enhancement Löbmann, Korbinian; Grohganz, Holger; Laitinen, Riikka European Journal of Pharmaceutics and Biopharmaceutics, Vol. 85, Issue 3 https://doi.org/10.1016/j.ejpb.2013.03.014	journal	November 2013
Effect of Organic Acids on Molecular Mobility, Physical Stability, and Dissolution of Ternary Ketoconazole Spray-Dried Dispersions Fung, Michelle H.; Suryanarayanan, Raj Molecular Pharmaceutics, Vol. 16, Issue 1 https://doi.org/10.1021/acs.molpharmaceut.8b00593	journal	October 2018
Compression-Induced Crystallization in Sucrose-Polyvinylpyrrolidone Amorphous Solid Dispersions Be̅rziņš, Ka̅rlis; Suryanarayanan, Raj Crystal Growth & Design, Vol. 18, Issue 2 https://doi.org/10.1021/acs.cgd.7b01305	journal	January 2018
The Role of Polymer Concentration on the Molecular Mobility and Physical Stability of Nifedipine Solid Dispersions Kothari, Khushboo; Ragoonanan, Vishard; Suryanarayanan, Raj Molecular Pharmaceutics, Vol. 12, Issue 5 https://doi.org/10.1021/mp500800c	journal	April 2015
Amorphous solid dispersions: Rational selection of a manufacturing process Vasconcelos, Teófilo; Marques, Sara; das Neves, José Advanced Drug Delivery Reviews, Vol. 100 https://doi.org/10.1016/j.addr.2016.01.012	journal	May 2016
Isothermal Crystallization and Time–Temperature Transformation of Amorphous Nifedipine: A Case of Polymorphism Formation and Conversion Cheng, Sixue; McKenna, Gregory B. Molecular Pharmaceutics, Vol. 18, Issue 7 https://doi.org/10.1021/acs.molpharmaceut.1c00331	journal	June 2021
Dual Functionality of Bile Acid: Physical Stabilization of Drugs in the Amorphous Form and Solubility Enhancement in Solution Lalge, Rahul; Kaur, Navpreet; Duggirala, Naga Kiran Molecular Pharmaceutics, Vol. 19, Issue 7 https://doi.org/10.1021/acs.molpharmaceut.2c00294	journal	June 2022
Role of polymer chemistry in influencing crystal growth rates from amorphous felodipine Kestur, Umesh S.; Taylor, Lynne S. CrystEngComm, Vol. 12, Issue 8 https://doi.org/10.1039/c001905d	journal	January 2010
New Strategies for Improving the Development and Performance of Amorphous Solid Dispersions Haser, Abbe; Zhang, Feng AAPS PharmSciTech, Vol. 19, Issue 3 https://doi.org/10.1208/s12249-018-0953-z	journal	January 2018
A kinetic treatment of glass formation: IV. Crystallization on reheating a glass Onorato, P. I. K.; Uhlmann, D. R.; Hopper, R. W. Journal of Non-Crystalline Solids, Vol. 41, Issue 2 https://doi.org/10.1016/0022-3093(80)90164-7	journal	November 1980
Applications of Powder X-Ray Diffraction in Small Molecule Pharmaceuticals: Achievements and Aspirations Thakral, Naveen K.; Zanon, Roger L.; Kelly, Ron C. Journal of Pharmaceutical Sciences, Vol. 107, Issue 12 https://doi.org/10.1016/j.xphs.2018.08.010	journal	December 2018
Sudden Rise of Crystal Growth Rate of Nifedipine near Tg without and with Polyvinylpyrrolidone Ishida, Hajime; Wu, Tian; Yu, Lian Journal of Pharmaceutical Sciences, Vol. 96, Issue 5 https://doi.org/10.1002/jps.20925	journal	May 2007
Role of the Strength of Drug–Polymer Interactions on the Molecular Mobility and Crystallization Inhibition in Ketoconazole Solid Dispersions Mistry, Pinal; Mohapatra, Sarat; Gopinath, Tata Molecular Pharmaceutics, Vol. 12, Issue 9 https://doi.org/10.1021/acs.molpharmaceut.5b00333	journal	July 2015
Solubility Advantage of Amorphous Drugs and Pharmaceutical Cocrystals Babu, N. Jagadeesh; Nangia, Ashwini Crystal Growth & Design, Vol. 11, Issue 7 https://doi.org/10.1021/cg200492w	journal	July 2011
Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-, 3-cyano-, 4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine Triggle, A. M.; Shefter, E.; Triggle, D. J. Journal of Medicinal Chemistry, Vol. 23, Issue 12 https://doi.org/10.1021/jm00186a029	journal	December 1980
Isothermal Crystallization Monitoring and Time–Temperature-Transformation of Amorphous GDC-0276: Differential Scanning Calorimetric and Rheological Measurements Cheng, Sixue; Chakravarty, Paroma; Nagapudi, Karthik Molecular Pharmaceutics, Vol. 18, Issue 1 https://doi.org/10.1021/acs.molpharmaceut.0c00776	journal	December 2020
Effect of polymers on nucleation and crystal growth of amorphous acetaminophen Trasi, Niraj S.; Taylor, Lynne S. CrystEngComm, Vol. 14, Issue 16 https://doi.org/10.1039/c2ce25374g	journal	January 2012
Pharmaceutical Applications of Hot-Melt Extrusion: Part I Crowley, Michael M.; Zhang, Feng; Repka, Michael A. Drug Development and Industrial Pharmacy, Vol. 33, Issue 9 https://doi.org/10.1080/03639040701498759	journal	January 2007
Assessment of granulation technologies for an API with poor physical properties Dalziel, Gena; Nauka, Ewa; Zhang, Feng Drug Development and Industrial Pharmacy, Vol. 39, Issue 7 https://doi.org/10.3109/03639045.2012.687744	journal	June 2012
Hydrogen Bonding Interactions in Amorphous Indomethacin and Its Amorphous Solid Dispersions with Poly(vinylpyrrolidone) and Poly(vinylpyrrolidone- co -vinyl acetate) Studied Using ¹³ C Solid-State NMR Yuan, Xiaoda; Xiang, Tian-Xiang; Anderson, Bradley D. Molecular Pharmaceutics, Vol. 12, Issue 12 https://doi.org/10.1021/acs.molpharmaceut.5b00705	journal	November 2015
A kinetic treatment of glass formation VII: Transient nucleation in non-isothermal crystallization during cooling Yinnon, H.; Uhlmann, D. R. Journal of Non-Crystalline Solids, Vol. 50, Issue 2 https://doi.org/10.1016/0022-3093(82)90266-6	journal	July 1982
Crystallization Propensity of Amorphous Pharmaceuticals: Kinetics and Thermodynamics Krishna Kumar, N. S.; Suryanarayanan, Raj Molecular Pharmaceutics, Vol. 19, Issue 2 https://doi.org/10.1021/acs.molpharmaceut.1c00839	journal	January 2022
On the physical dimensions of the Avrami constant Maffezzoli, Alfonso; Kenny, JoséM.; Torre, Luigi Thermochimica Acta, Vol. 269-270 https://doi.org/10.1016/0040-6031(95)02368-2	journal	December 1995
Developing HME-Based Drug Products Using Emerging Science: a Fast-Track Roadmap from Concept to Clinical Batch Matić, Josip; Paudel, Amrit; Bauer, Hannes AAPS PharmSciTech, Vol. 21, Issue 5 https://doi.org/10.1208/s12249-020-01713-0	journal	June 2020
Crystallization tendency of APIs possessing different thermal and glass related properties in amorphous solid dispersions Kapourani, Afroditi; Vardaka, Elisavet; Katopodis, Konstantinos International Journal of Pharmaceutics, Vol. 579 https://doi.org/10.1016/j.ijpharm.2020.119149	journal	April 2020
Hot Melt Extrusion: Highlighting Physicochemical Factors to Be Investigated While Designing and Optimizing a Hot Melt Extrusion Process Censi, Roberta; Gigliobianco, Maria Rosa; Casadidio, Cristina Pharmaceutics, Vol. 10, Issue 3 https://doi.org/10.3390/pharmaceutics10030089	journal	July 2018
Recent advances in co-amorphous drug formulations Dengale, Swapnil Jayant; Grohganz, Holger; Rades, Thomas Advanced Drug Delivery Reviews, Vol. 100 https://doi.org/10.1016/j.addr.2015.12.009	journal	May 2016
Granulation, Phase Change, and Microstructure Kinetics of Phase Change. III Avrami, Melvin The Journal of Chemical Physics, Vol. 9, Issue 2, p. 177-184 https://doi.org/10.1063/1.1750872	journal	February 1941
Solid-state properties and dissolution behaviour of tablets containing co-amorphous indomethacin–arginine Lenz, Elisabeth; Jensen, Katrine Tarp; Blaabjerg, Lasse Ingerslev European Journal of Pharmaceutics and Biopharmaceutics, Vol. 96 https://doi.org/10.1016/j.ejpb.2015.07.011	journal	October 2015
Solid dispersion of poorly water‐soluble drugs: Early promises, subsequent problems, and recent breakthroughs Serajuddin, Abu T. M. Journal of Pharmaceutical Sciences, Vol. 88, Issue 10 https://doi.org/10.1021/js980403l	journal	October 1999
Drug-Excipient Interactions: Effect on Molecular Mobility and Physical Stability of Ketoconazole–Organic Acid Coamorphous Systems Fung, Michelle H.; DeVault, Marla; Kuwata, Keith T. Molecular Pharmaceutics, Vol. 15, Issue 3 https://doi.org/10.1021/acs.molpharmaceut.7b00932	journal	January 2018
Amorphous Drug–Polymer Salt with High Stability under Tropical Conditions and Fast Dissolution: The Case of Clofazimine and Poly(acrylic acid) Gui, Yue; McCann, Erin C.; Yao, Xin Molecular Pharmaceutics, Vol. 18, Issue 3 https://doi.org/10.1021/acs.molpharmaceut.0c01180	journal	February 2021
Characterization of Physico-Mechanical Properties of Indomethacin and Polymers to Assess their Suitability for Hot-Melt Extrusion Processs as a Means to Manufacture Solid Dispersion/Solution**Mailing address of the place where the work was carried out, Hoffmann-La Roche, Inc., 340 Kingsland Street, Nutley, NJ, 07110. Chokshi, Rina J.; Sandhu, Harpreet K.; Iyer, Raman M. Journal of Pharmaceutical Sciences, Vol. 94, Issue 11 https://doi.org/10.1002/jps.20385	journal	November 2005
Effects of extrusion process parameters on the dissolution behavior of indomethacin in Eudragit® E PO solid dispersions Liu, Huiju; Wang, Peng; Zhang, Xueyan International Journal of Pharmaceutics, Vol. 383, Issue 1-2 https://doi.org/10.1016/j.ijpharm.2009.09.003	journal	January 2010
Crystallization from the Amorphous State: Nucleation–Growth Decoupling, Polymorphism Interplay, and the Role of Interfaces Descamps, Marc; Dudognon, Emeline Journal of Pharmaceutical Sciences, Vol. 103, Issue 9 https://doi.org/10.1002/jps.24016	journal	September 2014
The application of temperature-composition phase diagrams for hot melt extrusion processing of amorphous solid dispersions to prevent residual crystallinity Moseson, Dana E.; Taylor, Lynne S. International Journal of Pharmaceutics, Vol. 553, Issue 1-2 https://doi.org/10.1016/j.ijpharm.2018.10.055	journal	December 2018
A kinetic treatment of glass formation Uhlmann, D. R. Journal of Non-Crystalline Solids, Vol. 7, Issue 4 https://doi.org/10.1016/0022-3093(72)90269-4	journal	May 1972
Determination of the crystal structure of nifedipine form C by synchrotron powder diffraction Bortolotti, Mauro; Lonardelli, Ivan; Pepponi, Giancarlo Acta Crystallographica Section B Structural Science, Vol. 67, Issue 4 https://doi.org/10.1107/s0108768111021653	journal	July 2011
Amorphous pharmaceutical solids: preparation, characterization and stabilization Yu, Lian Advanced Drug Delivery Reviews, Vol. 48, Issue 1 https://doi.org/10.1016/s0169-409x(01)00098-9	journal	May 2001
Isothermal nanocrystallization kinetics during polymorphic transformation Sinha, I.; Mandal, R. K. Journal of Non-Crystalline Solids, Vol. 355, Issue 6 https://doi.org/10.1016/j.jnoncrysol.2008.12.006	journal	March 2009
A kinetic treatment of glass formation. VIII: Critical cooling rates for Na2OSiO2 and K2OSiO2 glasses Fang, Chih-Yao; Yinnon, H.; Uhlmann, D. R. Journal of Non-Crystalline Solids, Vol. 57, Issue 3 https://doi.org/10.1016/0022-3093(83)90433-7	journal	September 1983
Continuous cooling approximation for the formation of a glass Barandiarán, J. M.; Colmenero, J. Journal of Non-Crystalline Solids, Vol. 46, Issue 3 https://doi.org/10.1016/0022-3093(81)90006-5	journal	December 1981
The Role of Drug–Polymer Hydrogen Bonding Interactions on the Molecular Mobility and Physical Stability of Nifedipine Solid Dispersions Kothari, Khushboo; Ragoonanan, Vishard; Suryanarayanan, Raj Molecular Pharmaceutics, Vol. 12, Issue 1 https://doi.org/10.1021/mp5005146	journal	November 2014
Amorphous Drug-Polymer Salts Yao, Xin; Neusaenger, Amy Lan; Yu, Lian Pharmaceutics, Vol. 13, Issue 8 https://doi.org/10.3390/pharmaceutics13081271	journal	August 2021
Assessing Mixing Quality of a Copovidone-TPGS Hot Melt Extrusion Process with Atomic Force Microscopy and Differential Scanning Calorimetry Lamm, Matthew S.; DiNunzio, James; Khawaja, Nazia N. AAPS PharmSciTech, Vol. 17, Issue 1 https://doi.org/10.1208/s12249-015-0387-9	journal	August 2015
Effect of Polymer Molecular Weight on the Crystallization Behavior of Indomethacin Amorphous Solid Dispersions Mohapatra, Sarat; Samanta, Subarna; Kothari, Khushboo Crystal Growth & Design, Vol. 17, Issue 6 https://doi.org/10.1021/acs.cgd.7b00096	journal	May 2017
Hot-melt extrusion in the pharmaceutical industry: toward filing a new drug application Simões, Marta F.; Pinto, Rui M. A.; Simões, Sérgio Drug Discovery Today, Vol. 24, Issue 9 https://doi.org/10.1016/j.drudis.2019.05.013	journal	September 2019
A Simultaneous Differential Scanning Calorimetry–X-ray Diffraction Study of Olanzapine Crystallization from Amorphous Solid Dispersions Askin, Sean; Gonçalves, Andrea D.; Zhao, Min Molecular Pharmaceutics, Vol. 17, Issue 11 https://doi.org/10.1021/acs.molpharmaceut.0c00846	journal	October 2020
A supramolecular synthon approach to design amorphous solid dispersions with exceptional physical stability Duggirala, Naga Kiran; Li, Jinghan; Kumar, N. S. Krishna Chemical Communications, Vol. 55, Issue 39 https://doi.org/10.1039/c9cc02021g	journal	January 2019
Kinetics of Phase Change. I General Theory Avrami, Melvin The Journal of Chemical Physics, Vol. 7, Issue 12, p. 1103-1112 https://doi.org/10.1063/1.1750380	journal	December 1939
Nucleating heterogeneities and glass formation Onorato, P. I. K.; Uhlmann, D. R. Journal of Non-Crystalline Solids, Vol. 22, Issue 2 https://doi.org/10.1016/0022-3093(76)90066-1	journal	November 1976
Glass-Formers and Viscous Liquid Slowdown since David Turnbull: Enduring Puzzles and New Twists Angell, C. A. MRS Bulletin, Vol. 33, Issue 5 https://doi.org/10.1557/mrs2008.108	journal	May 2008
Physical Properties of Solid Molecular Dispersions of Indomethacin with Poly(vinylpyrrolidone) and Poly(vinylpyrrolidone-co-vinyl-acetate) in Relation to Indomethacin Crystallization Matsumoto, Takahiro; Zografi, George Pharmaceutical Research, Vol. 16, Issue 11, p. 1722-1728 https://doi.org/10.1023/a:1018906132279	journal	November 1999
One- and two-step calorimetric studies of crystallization kinetics in simple ionic glass-forming liquids. 1. Calcium nitrate-potassium nitrate system Senapati, H.; Kadiyala, K. K.; Angell, C. A. The Journal of Physical Chemistry, Vol. 95, Issue 18 https://doi.org/10.1021/j100171a060	journal	September 1991
Glass Forming Ability of Amorphous Drugs Investigated by Continuous Cooling and Isothermal Transformation Blaabjerg, Lasse I.; Lindenberg, Eleanor; Löbmann, Korbinian Molecular Pharmaceutics, Vol. 13, Issue 9 https://doi.org/10.1021/acs.molpharmaceut.6b00650	journal	August 2016

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