Amorphous dispersions of flubendazole in hydroxypropyl methylcellulose: Formulation stability assisted by pair distribution function analysis

Bezzon, Vinicius D. N.; Ferreira, Fabio F.; Smith, Pamela; Benmore, Chris J.; Byrn, Stephen R.; de Araujo, Gabriel L. B.

doi:10.1016/j.ijpharm.2021.120500

Title: Amorphous dispersions of flubendazole in hydroxypropyl methylcellulose: Formulation stability assisted by pair distribution function analysis

Journal Article · Sat May 01 00:00:00 EDT 2021 · International Journal of Pharmaceutics

DOI:https://doi.org/10.1016/j.ijpharm.2021.120500· OSTI ID:1781671

Bezzon, Vinicius D. N. ^[1]; Ferreira, Fabio F. ^[2]; Smith, Pamela ^[3]; Benmore, Chris J. ^[4]; Byrn, Stephen R. ^[5]; de Araujo, Gabriel L. B. ^[6]

Federal University of ABC (UFABC), Santo Andre, SP (Brazil); Improved Pharma, West Lafayette, IN (United States)
Federal University of ABC (UFABC), Santo Andre, SP (Brazil)
Improved Pharma, West Lafayette, IN (United States)
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Improved Pharma, West Lafayette, IN (United States); Purdue Univ., West Lafayette, IN (United States)
Univ. of Sao Paulo (Brazil)

Here, we use X-ray pair distribution function (PDF) analysis applied to high-energy synchrotron X-ray powder diffraction data to evaluate the amorphous solid dispersions interactions and their aging stability. The obtained systems are based on hydroxypropyl methylcellulose (hypromellose) derivatives and flubendazole (FBZ) drug dispersions prepared using a spray-dryer technique. We carry out stability studies under aging parameters (40 °C/75% relative humidity) to tune the systems’ recrystallization. The results reveal that ion-base interactions between the drug-polymer matrix are responsible for reducing clustering processes yielding slower recrystallization and different ordering in the hypromellose phthalate (HPMCP/FBZ) and hypromellose acetate succinate (HPMC-AS/FBZ) systems and complete drug clustering in hypromellose (HPMC-E3/FBZ). The structural ordering was accessed using differential X-ray PDFs that revealed the region between 3.5 Å and 5.0 Å could be related to FBZ intermolecular interactions and is more ordered for the least stable system (HPMC-E3/FBZ) and less ordered for the most stable system (HPMCP/FBZ). These results show that the ion-base interactions between drug and matrix occur at these intermolecular distances.

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

Sponsoring Organization:: Sao Paulo Research Foundation (FAPESP); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357; 2018/11990-5; 2019/04998-2

OSTI ID:: 1781671

Journal Information:: International Journal of Pharmaceutics, Vol. 600; ISSN 0378-5173

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (27)

Exploring the Potential of Flubendazole in Filariasis Control: Evaluation of the Systemic Exposure for Different Pharmaceutical Preparations Ceballos, Laura; Mackenzie, Charles; Geary, Timothy PLoS Neglected Tropical Diseases, Vol. 8, Issue 5 https://doi.org/10.1371/journal.pntd.0002838	journal	May 2014
A Review of High-Energy X-Ray Diffraction from Glasses and Liquids Benmore, C. J. ISRN Materials Science, Vol. 2012 https://doi.org/10.5402/2012/852905	journal	January 2012
Probing the Amorphous State of Pharmaceutical Compounds Within Mesoporous Material Using Pair Distribution Function Analysis Garcia-Bennett, Alfonso E.; Lau, Michael; Bedford, Nicholas Journal of Pharmaceutical Sciences, Vol. 107, Issue 8 https://doi.org/10.1016/j.xphs.2018.03.029	journal	August 2018
Recrystallization, Phase Composition, and Local Structure of Amorphous Lactose from the Total Scattering Pair Distribution Function Terban, Maxwell W.; Cheung, Eugene Y.; Krolikowski, Paul Crystal Growth & Design, Vol. 16, Issue 1 https://doi.org/10.1021/acs.cgd.5b01100	journal	November 2015
Evaluation of Three Amorphous Drug Delivery Technologies to Improve the Oral Absorption of Flubendazole Vialpando, Monica; Smulders, Stefanie; Bone, Scott Journal of Pharmaceutical Sciences, Vol. 105, Issue 9 https://doi.org/10.1016/j.xphs.2016.03.003	journal	September 2016
Characterisation of amorphous and nanocrystalline molecular materials by total scattering Billinge, Simon J. L.; Dykhne, Timur; Juhás, Pavol CrystEngComm, Vol. 12, Issue 5 https://doi.org/10.1039/B915453A	journal	January 2010
A New Thermodynamically Favored Flubendazole/Maleic Acid Binary Crystal Form: Structure, Energetics, and in Silico PBPK Model-Based Investigation de Araujo, Gabriel L. B.; Ferreira, Fabio Furlan; Bernardes, Carlos E. S. Crystal Growth & Design, Vol. 18, Issue 4 https://doi.org/10.1021/acs.cgd.7b01807	journal	February 2018
TOPAS and TOPAS-Academic : an optimization program integrating computer algebra and crystallographic objects written in C++ Coelho, Alan A. Journal of Applied Crystallography, Vol. 51, Issue 1 https://doi.org/10.1107/S1600576718000183	journal	February 2018
Local Structure of Ion Pair Interaction in Lapatinib Amorphous Dispersions characterized by Synchrotron X-Ray diffraction and Pair Distribution Function Analysis de Araujo, Gabriel L. B.; Benmore, Chris J.; Byrn, Stephen R. Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/srep46367	journal	April 2017
Investigating the Interaction Pattern and Structural Elements of a Drug–Polymer Complex at the Molecular Level Nie, Haichen; Mo, Huaping; Zhang, Mingtao Molecular Pharmaceutics, Vol. 12, Issue 7 https://doi.org/10.1021/acs.molpharmaceut.5b00162	journal	June 2015
Structural Characterization and Aging of Glassy Pharmaceuticals made Using Acoustic Levitation Benmore, Chris J.; Weber, J. K. R.; Tailor, Amit N. Journal of Pharmaceutical Sciences, Vol. 102, Issue 4 https://doi.org/10.1002/jps.23464	journal	April 2013
Pair distribution functions of amorphous organic thin films from synchrotron X-ray scattering in transmission mode Shi, Chenyang; Teerakapibal, Rattavut; Yu, Lian IUCrJ, Vol. 4, Issue 5 https://doi.org/10.1107/S2052252517009344	journal	July 2017
Investigation of Drug–Excipient Interactions in Lapatinib Amorphous Solid Dispersions Using Solid-State NMR Spectroscopy Song, Yang; Yang, Xinghao; Chen, Xin Molecular Pharmaceutics, Vol. 12, Issue 3 https://doi.org/10.1021/mp500692a	journal	January 2015
Atomic pair distribution function: a revolution in the characterization of nanostructured pharmaceuticals Billinge, Simon JL Nanomedicine, Vol. 10, Issue 16 https://doi.org/10.2217/nnm.15.116	journal	August 2015
Hydroxypropyl Methylcellulose Acetate Succinate-Based Spray-Dried Dispersions: An Overview Friesen, Dwayne T.; Shanker, Ravi; Crew, Marshall Molecular Pharmaceutics, Vol. 5, Issue 6 https://doi.org/10.1021/mp8000793	journal	November 2008
PDFgetX2: a GUI-driven program to obtain the pair distribution function from X-ray powder diffraction data Qiu, Xiangyun; Thompson, Jeroen W.; Billinge, Simon J. L. Journal of Applied Crystallography, Vol. 37, Issue 4, p. 678-678 https://doi.org/10.1107/S0021889804011744	journal	July 2004
A profile refinement method for nuclear and magnetic structures Rietveld, H. M. Journal of Applied Crystallography, Vol. 2, Issue 2, p. 65-71 https://doi.org/10.1107/S0021889869006558	journal	June 1969
Comparison of Flubendazole and Diethylcarbamazine in Treatment of Onchocerciasis Dominguez-Vazquez, Alfredo; Taylor, HughR.; Ruvalcaba-Macias, A. M. The Lancet, Vol. 321, Issue 8317 https://doi.org/10.1016/S0140-6736(83)92753-8	journal	January 1983
Accurate Structure Determination of Mo ₆ S _y I _z Nanowires from Atomic Pair Distribution Function (PDF) Analysis Paglia, Gianluca; Božin, Emil S.; Vengust, Damjan Chemistry of Materials, Vol. 18, Issue 1 https://doi.org/10.1021/cm051833x	journal	January 2006
Characterizing an Amorphous System Exhibiting Trace Crystallinity: A Case Study with Saquinavir Heinz, Andrea; Strachan, Clare J.; Atassi, Faraj Crystal Growth & Design, Vol. 8, Issue 1 https://doi.org/10.1021/cg700912q	journal	January 2008
A comparison of various commonly used correlation functions for describing total scattering Keen, David A. Journal of Applied Crystallography, Vol. 34, Issue 2 https://doi.org/10.1107/S0021889800019993	journal	April 2001
Towards solution and refinement of organic crystal structures by fitting to the atomic pair distribution function Prill, Dragica; Juhás, Pavol; Billinge, Simon J. L. Acta Crystallographica Section A Foundations and Advances, Vol. 72, Issue 1 https://doi.org/10.1107/S2053273315022457	journal	January 2016
Scherrer after sixty years: A survey and some new results in the determination of crystallite size Langford, J. I.; Wilson, A. J. C. Journal of Applied Crystallography, Vol. 11, Issue 2 https://doi.org/10.1107/S0021889878012844	journal	April 1978
Characterization of amorphous API:Polymer mixtures using X-ray powder diffraction Newman, Ann; Engers, David; Bates, Simon Journal of Pharmaceutical Sciences, Vol. 97, Issue 11 https://doi.org/10.1002/jps.21352	journal	November 2008
Illustrated formalisms for total scattering data: a guide for new practitioners Peterson, Peter F.; Olds, Daniel; McDonnell, Marshall T. Journal of Applied Crystallography, Vol. 54, Issue 1 https://doi.org/10.1107/S1600576720015630	journal	February 2021
Two-dimensional detector software: From real detector to idealised image or two-theta scan Hammersley, A. P.; Svensson, S. O.; Hanfland, M. High Pressure Research, Vol. 14, Issue 4-6, p. 235-248 https://doi.org/10.1080/08957959608201408	journal	January 1996
X-ray Intermolecular Structure Factor ( XISF ): separation of intra- and intermolecular interactions from total X-ray scattering data Mou, Q.; Benmore, C. J.; Yarger, J. L. Journal of Applied Crystallography, Vol. 48, Issue 3 https://doi.org/10.1107/S1600576715005518	journal	May 2015

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60 APPLIED LIFE SCIENCES
amorphous structure
flubendazole
hypromellose derivatives
pair distribution function

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