Monitoring of Isothermal Crystallization and Time-Temperature Transformation of Amorphous Felodipine: The Time-Domain Nuclear Magnetic Resonance Method.


Journal

AAPS PharmSciTech
ISSN: 1530-9932
Titre abrégé: AAPS PharmSciTech
Pays: United States
ID NLM: 100960111

Informations de publication

Date de publication:
19 Sep 2024
Historique:
received: 24 05 2024
accepted: 12 08 2024
medline: 20 9 2024
pubmed: 20 9 2024
entrez: 19 9 2024
Statut: epublish

Résumé

The isothermal crystallization process of felodipine has been investigated using the time-domain Nuclear Magnetic Resonance (NMR) method for amorphous bulk and ground samples. The obtained induction and crystallization times were then used to construct the time-temperature-transformation (TTT) diagram, both above and below the glass transition temperature (T

Identifiants

pubmed: 39299994
doi: 10.1208/s12249-024-02919-2
pii: 10.1208/s12249-024-02919-2
doi:

Substances chimiques

Felodipine OL961R6O2C

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

219

Informations de copyright

© 2024. The Author(s).

Références

Amidon GL, Lennernäs H, Shah VP, Crison JR. A Theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res. 1995;12:413–20.
pubmed: 7617530 doi: 10.1023/A:1016212804288
Hancock BC, Parks M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res. 2000;17(4):397–404.
pubmed: 10870982 doi: 10.1023/A:1007516718048
Gurunath S, Kumar PS, Basavaraj NK PP. Amorphous solid dispersion method for improving oral bioavailability of poorly water-soluble drugs. J Pharm Res. 2013;6:476–80.
Yu L. Amorphous pharmaceutical solids: Preparation, characterization and stabilization. Adv Drug Deliv Rev. 2001;48:27–42.
pubmed: 11325475 doi: 10.1016/S0169-409X(01)00098-9
Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility Advantage of amorphous pharmaceuticals: I. a thermodynamic analysis. J Pharm Sci. 2008;99:1254–64.
doi: 10.1002/jps.21903
Kothari K, Ragoonanan V, Suryanarayanan R. Influence of molecular mobility on the physical stability of amorphous pharmaceuticals in the supercooled and glassy states. Mol Pharmaceutics. 2014;11:3048–55.
doi: 10.1021/mp500229d
Newman A, Zografi G. What we need to know about solid-state isothermal crystallization of organic molecules from the amorphous state below the glass transition temperature. Mol Pharm. 2020;17:1761–77.
pubmed: 32275832 doi: 10.1021/acs.molpharmaceut.0c00181
Bhattacharya S, Suryanarayanan RAJ. Local mobility in amorphous pharmaceuticals — characterization and implications on stability. J Am Pharm Assoc. 2009;98:2935–53.
Wang Y, Wang Y, Cheng J, Chen H, Xu J, Liu Z, et al. Recent advances in the application of characterization pharmaceutical solids. Crystals. 2021;11:1440.
doi: 10.3390/cryst11121440
Kumar NSK, Suryanarayanan R. Crystallization propensity of amorphous pharmaceuticals: kinetics and thermodynamics. Mol Pharm. 2022;19:472–83.
doi: 10.1021/acs.molpharmaceut.1c00839
Cheng S, Chakravarty P, Nagapudi K, Mckenna GB. Isothermal crystallization monitoring and time − temperature- transformation of amorphous GDC-0276: differential scanning calorimetric and rheological measurements. Mol Pharm. 2021;18:158–73.
pubmed: 33259220 doi: 10.1021/acs.molpharmaceut.0c00776
Zhou D, Grant DJW, Zhang GGZ, Law D, Schmitt EA. A calorimetric investigation of thermodynamic and molecular mobility contributions to the physical stability of two pharmaceutical glasses. J Pharm Sci. 2007;96:71–83.
pubmed: 17031846 doi: 10.1002/jps.20633
Bhugra C, Shmeis R, Steven L, Krill MJP. Prediction of onset of crystallization from experimental relaxation times. Ii. comparison between predicted and experimental onset times. J Pharm Sci. 2012;101:2271–80.
Kestur US, Ivanesivic I, Alonzo DE, Taylor LS. Influence of particle size on the crystallization kinetics of amorphous felodipine powders. Powder Technol. 2013;236:197–204.
doi: 10.1016/j.powtec.2012.02.010
D’Amore A, Kenny JM, Nicolais L, Tucci V. Dynamic-mechanical and dielectric characterization of PEEK crystallization. Polym Eng Sci. 1990;30:314–20.
doi: 10.1002/pen.760300509
Pajzderska A, Fojud Z, Jarek M, Wąsicki J. NMR relaxometry in the investigation of the kinetics of the recrystallization of felodipine. Powder Technol. 2019;347:35–41.
doi: 10.1016/j.powtec.2019.02.041
Pajzderska A, Jenczyk J, Embs JP, Wąsicki J. Exploring molecular reorientations in amorphous and recrystallized felodipine at the microscopic level. RSC Adv. 2020;10:37346–57.
pubmed: 35521258 pmcid: 9057141 doi: 10.1039/D0RA07266D
Cheng S, McKenna GB. Isothermal crystallization and time-temperature transformation of amorphous nifedipine: a case of polymorphism formation and conversion. Mol Pharm. 2021;18:2786–802.
pubmed: 34105978 doi: 10.1021/acs.molpharmaceut.1c00331
Lalge R, Kumar NSK, Suryanarayanan R. Understanding the effect of nucleation in amorphous solid dispersions through time-temperature transformation. Mol Pharm. 2023;20:4196–209.
pubmed: 37358932 doi: 10.1021/acs.molpharmaceut.3c00313
Blaabjerg LI, Lindenberg E, Löbmann K, Grohganz H, Rades T. Glass forming ability of amorphous drugs investigated by continuous cooling and isothermal transformation. Mol Pharm. 2016;13:3318–25.
pubmed: 27529364 doi: 10.1021/acs.molpharmaceut.6b00650
Schwartz DRA, JB. Calcium-antagonist drugs. N Engl J Med. 1999;341:1447–57.
pubmed: 10547409 doi: 10.1056/NEJM199911043411907
Cheng S. Glass Transition and crystallization of amorphous pharmaceuticals: time-temperature-transformation diagram and crystallization suppression. Texas Tech University; 2021. https://ttu-ir.tdl.org/home .
Pajzderska A, Drużbicki K, Gonzalez MA, Jenczyk J, Mielcarek J, Wąsicki J. Diversity of methyl group dynamics in felodipine: a DFT supported NMR and QENS study. CrystEngComm. 2018;20:7371–85.
doi: 10.1039/C8CE01605D
Kothari K. The role of molecular mobility and hydrogen bonding interactions on the physical stability of amorphous pharmaceuticals University of Minnesota Thesis. 2014.
Tang XC, Pikal MJ, Taylor LS. A Spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers. Pharm Res. 2002;19:484–90.
pubmed: 12033384 doi: 10.1023/A:1015199713635
Pajzderska A, Gonzalez MA, Embs JP, Mielcarek J, Wąsicki JW. Dynamics of an amorphous pharmacologically active compound-diazepam: A QENS study combined with molecular dynamics simulations. RSC Adv. 2017;7:35504–15.
doi: 10.1039/C7RA06133A
Hussan KPS, Thayyil MS, Deshpande SK, Jinitha TV, Manoj KNK. Molecular dynamics, physical and thermal stability of neat amorphous amlodipine besylate and in binary mixture. Eur J Pharm Sci. 2018;119:268–78.
doi: 10.1016/j.ejps.2018.04.030
Gupta J, Nunes C, Vyas S, Jonnalagadda S. Prediction of solubility parameters and miscibility of pharmaceutical compounds by molecular dynamics simulations. J Phys Chem B. 2011;115:2014–23.
pubmed: 21306175 doi: 10.1021/jp108540n
Gerges J, Affouard F. Predictive Calculation of the crystallization tendency of model pharmaceuticals in the supercooled state from molecular dynamics simulations. J Phys Chem B. 2015;119:10768–83.
pubmed: 26226388 doi: 10.1021/acs.jpcb.5b05557
Gerges J, Affouard F. Insight from molecular dynamics simulations on the crystallization tendency of indomethacin polymorphs in the undercooled liquid state. J Pharm Sci. 2020;109:1086–95.
pubmed: 31678250 doi: 10.1016/j.xphs.2019.10.054
Xiang T, Anderson BD. Molecular dynamics simulation of amorphous indomethacin-poly (vinylpyrrolidone) glasses: Solubility and hydrogen bonding interactions. J Pharm Sci. 2013;102:876–91.
pubmed: 23280486 doi: 10.1002/jps.23353
Barmpalexis P, Karagianni A, Kachrimanis K. Molecular simulations for amorphous drug formulation: Polymeric matrix properties relevant to hot-melt extrusion. Eur J Pharm Sci. 2019;130:260–8.
pubmed: 30735824 doi: 10.1016/j.ejps.2019.02.004
Pajzderska A, Gonzalez MA. Molecular dynamics simulations of selected amorphous stilbenoids and their amorphous solid dispersions with poly(vinylpyrrolidone). J Pharm Sci. 2023;112:2444–52.
pubmed: 36965843 doi: 10.1016/j.xphs.2023.03.013
Salo-Ahen OMH, Alanko I, Bhadane R, Bonvin AMJJ, Honorato RV, Hossain S, Juffer AH, Kabedev A, Lahtela-Kakkonen M, Larsen AS, et al. Molecular dynamics simulations in drug discovery and pharmaceutical development. Processes. 2021;9:71.
doi: 10.3390/pr9010071
Mollazadeh S, Sahebkar A, Shahlaei M, Moradi S. Nano drug delivery systems: Molecular dynamic simulation. J Mol Liq. 2021;332:115823.
doi: 10.1016/j.molliq.2021.115823
Fossheim R. Crystal structure of the dihydropyridine ca2+ antagonist felodipine. Dihydropyridine binding prerequisites assessed from crystallographic data. J Med Chem. 1986;29:305–7.
pubmed: 3005572 doi: 10.1021/jm00152a023
Hatakeyama T, Quinn FX. Thermal Analysis: Fundamentals and Applications to Polymer Science. New York: Wiley; 1994.
PeakFit-Jandel Scientific Software, San Rafael, CA. https://www.systat.com/products/PeakFit/ .
Thompson AP, Aktulga HM, Berger R, Bolintineanu DS, Brown WM, Crozier PS, in’t Veld PJ, Kohlmeyer A, Moore SG, Nguyen TD, Shan R, Stevens MJ, Tranchida J, Trott CPS. LAMMPS - a flexible simulation tool for particle-based materials modeling at the atomic, meso, and continuum scales. Comp Phys Comm. 2022;271:10817.
doi: 10.1016/j.cpc.2021.108171
Materials Studio Modelling Environment, Version 6.5, Accelrys, Inc., San Diego; 2009. https://www.3ds.com/products/biovia/materials-studio .
Allen MP, Tildesley TJ. Computer simulation of liquids. Oxford: Oxford University Press; 2002.
Banks JL, Beard HS, Cao Y, Cho AE, Damm W, Farid R, Felts AK, Halgren TA, Mainz DT, Maple JR, Murphy R, Philipp DM, Repasky MP, Zhang LY, Berne BJ, Friesner RA, Gallicchio ELR. Integrated modeling program, applied chemical theory (IMPACT). J Comput Chem. 2005;26:1752–80.
pubmed: 16211539 pmcid: 2742605 doi: 10.1002/jcc.20292
Hinsen K, Pellegrini E, Stachura S, Kneller GR. NMoldyn 3: Using task farming for a parallel spectroscopy-oriented analysis of molecular dynamics simulations. J Comput Chem. 2012;33:2043–8.
pubmed: 22685090 doi: 10.1002/jcc.23035
Bloembergen N, Purcell EM, Pound RV. Relaxation effects in nuclear magnetic resonance absorption. Phys Rev. 1948;73:679–712.
doi: 10.1103/PhysRev.73.679
Wu T, Yu L. Surface crystallization of indomethacin below T g. Pharm Res. 2006;23:2350–5.
pubmed: 16927184 doi: 10.1007/s11095-006-9023-4
Zhu L, Wong L, Yu L. Surface-enhanced crystallization of amorphous nifedipine. Mol Pharm. 2008;5:921–6.
pubmed: 19434917 doi: 10.1021/mp8000638
Zhu L, Jona J, Nagapudi K, Wu T. Fast surface crystallization of amorphous griseofulvin below Tg. Pharm Res. 2010;27:1558–67.
pubmed: 20414704 doi: 10.1007/s11095-010-0140-8
Vlassios A, Minoru Y, George Z. Effects of sorbed water on the crystallization of indomethacin from the amorphous state. J Pharm Sci. 1997;86:346–51.
doi: 10.1021/js9602711
Kestur US, Taylor LS. Evaluation of the crystal growth rate of felodipine polymorphs in the presence and absence of additives as a function of temperature. Cryst Growth Des. 2013;13:4349–54.
doi: 10.1021/cg400708p
Prada-Gracia D, Shevchuk RRF. The quest for self-consistency in hydrogen bond definitions. J Chem Phys. 2013;139:084501.
pubmed: 24007012 doi: 10.1063/1.4818885
Steiner T. The Hydrogen Bond in the Solid State. Angew Chem Int Ed. 2002;41:48–76.
doi: 10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U
Sun Y, Xi H, Ediger MD, Yu L. Diffusionless crystal growth from glass has precursor in equilibrium liquid. J Phys Chem B. 2008;112:661–4.
pubmed: 18095668 doi: 10.1021/jp709616c
Sun Y, Xi H, Chen S, Ediger MD, Yu L. Crystallization near glass transition: Transition from diffusion-controlled to diffusionless crystal growth studied with seven polymorphs. J Phys Chem B. 2008;112:5594–601.
pubmed: 18407712 doi: 10.1021/jp7120577

Auteurs

A Pajzderska (A)

Faculty of Physics, Adam Mickiewicz University, Uniwersytetu Poznańskiego 2, 61-614, Poznań, Poland. apajzder@amu.edu.pl.

M A Gonzalez (MA)

Institute Laue Langevin, 71 Avenue Des Martyrs, Grenoble, France.

M Jarek (M)

NanoBioMedical Centre, A. Mickiewicz University, Wszechnicy Piastowskiej 3, Poznan, Poland.

J Wąsicki (J)

Faculty of Physics, Adam Mickiewicz University, Uniwersytetu Poznańskiego 2, 61-614, Poznań, Poland.

Articles similaires

Photosynthesis Ribulose-Bisphosphate Carboxylase Carbon Dioxide Molecular Dynamics Simulation Cyanobacteria
Fucosyltransferases Drug Repositioning Molecular Docking Simulation Molecular Dynamics Simulation Humans
Receptor, Cannabinoid, CB1 Ligands Molecular Dynamics Simulation Protein Binding Thermodynamics

Classifications MeSH