Dehydration of Niclosamide Monohydrate Polymorphs: Different Mechanistic Pathways to the Same Product

Mann, Jen E.; Gao, Renee; Swift, Jennifer A.

doi:10.1021/acs.cgd.3c00322

Dehydration of Niclosamide Monohydrate Polymorphs: Different Mechanistic Pathways to the Same Product

Journal Article · 02 June 2023 · Crystal Growth and Design

DOI:https://doi.org/10.1021/acs.cgd.3c00322· OSTI ID:2423366

Mann, Jen E. ^[1]; Gao, Renee ^[1]; ^[1]

Georgetown University, Department of Chemistry, 37th and O Streets NW, Washington, District of Columbia 20057-1227, 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:: 2423366

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 7 Vol. 23; ISSN 1528-7483

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (49)

GSAS-II : the genesis of a modern open-source all purpose crystallography software package Toby, Brian H.; Von Dreele, Robert B. Journal of Applied Crystallography, Vol. 46, Issue 2 https://doi.org/10.1107/S0021889813003531	journal	March 2013
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
Preparation and physicochemical characterization of 5 niclosamide solvates and 1 hemisolvate van Tonder, Elsa C.; Mahlatji, Mabatane D.; Malan, Sarel F. AAPS PharmSciTech, Vol. 5, Issue 1 https://doi.org/10.1208/pt050112	journal	March 2004
A Prolific Solvate Former, Galunisertib, under the Pressure of Crystal Structure Prediction, Produces Ten Diverse Polymorphs Bhardwaj, Rajni M.; McMahon, Jennifer A.; Nyman, Jonas Journal of the American Chemical Society, Vol. 141, Issue 35 https://doi.org/10.1021/jacs.9b06634	journal	August 2019
A versatile sample-environment cell for non-ambient X-ray scattering experiments Chupas, Peter J.; Chapman, Karena W.; Kurtz, Charles Journal of Applied Crystallography, Vol. 41, Issue 4 https://doi.org/10.1107/S0021889808020165	journal	July 2008
Two New Polymorphs of Huperzine A Obtained from Different Dehydration Processes of One Monohydrate Zhang, Qi; Mei, Xuefeng Crystal Growth & Design, Vol. 16, Issue 6 https://doi.org/10.1021/acs.cgd.6b00493	journal	May 2016
Broad Spectrum Antiviral Agent Niclosamide and Its Therapeutic Potential Xu, Jimin; Shi, Pei-Yong; Li, Hongmin ACS Infectious Diseases, Vol. 6, Issue 5 https://doi.org/10.1021/acsinfecdis.0c00052	journal	March 2020
Discovery of O -Alkylamino-Tethered Niclosamide Derivatives as Potent and Orally Bioavailable Anticancer Agents Chen, Haijun; Yang, Zhengduo; Ding, Chunyong ACS Medicinal Chemistry Letters, Vol. 4, Issue 2 https://doi.org/10.1021/ml3003082	journal	January 2013
Model-free treatment of the dehydration kinetics of nedocromil sodium trihydrate Zhou, Deliang; Schmitt, Eric A.; Zhang, Geoff G. Z. Journal of Pharmaceutical Sciences, Vol. 92, Issue 7 https://doi.org/10.1002/jps.10400	journal	July 2003
New methods for evaluating kinetic parameters from thermal analysis data Friedman, Henry L. Journal of Polymer Science Part B: Polymer Letters, Vol. 7, Issue 1 https://doi.org/10.1002/pol.1969.110070109	journal	January 1969
Using Salt Cocrystals to Improve the Solubility of Niclosamide Grifasi, Francesca; Chierotti, Michele R.; Gaglioti, Katia Crystal Growth & Design, Vol. 15, Issue 4 https://doi.org/10.1021/acs.cgd.5b00106	journal	March 2015
Amorphous Solid Dispersions and the Contribution of Nanoparticles to In Vitro Dissolution and In Vivo Testing: Niclosamide as a Case Study Jara, Miguel O.; Warnken, Zachary N.; Williams, Robert O. Pharmaceutics, Vol. 13, Issue 1 https://doi.org/10.3390/pharmaceutics13010097	journal	January 2021
Pharmaceutical Cocrystals of Niclosamide Sanphui, Palash; Kumar, S. Sudalai; Nangia, Ashwini Crystal Growth & Design, Vol. 12, Issue 9 https://doi.org/10.1021/cg300784v	journal	August 2012
On the Formation and Desolvation Mechanism of Organic Molecule Solvates: A Structural Study of Methyl Cholate Solvates Be̅rziņš, Agris; Trimdale, Aija; Kons, Artis Crystal Growth & Design, Vol. 17, Issue 11 https://doi.org/10.1021/acs.cgd.7b00657	journal	October 2017
Identification of Niclosamide as a Novel Anticancer Agent for Adrenocortical Carcinoma Satoh, Kei; Zhang, Lisa; Zhang, Yaqin Clinical Cancer Research, Vol. 22, Issue 14 https://doi.org/10.1158/1078-0432.CCR-15-2256	journal	July 2016
Transforming Computed Energy Landscapes into Experimental Realities: The Role of Structural Rugosity Montis, Riccardo; Davey, Roger J.; Wright, Sarah E. Angewandte Chemie International Edition, Vol. 59, Issue 46 https://doi.org/10.1002/anie.202006939	journal	September 2020
Niclosamide Therapy for Tapeworm Infections Pearson, Richard D. Annals of Internal Medicine, Vol. 102, Issue 4 https://doi.org/10.7326/0003-4819-102-4-550	journal	April 1985
Access to Several Polymorphic Forms of (±)-Modafinil by Using Various Solvation–Desolvation Processes Mahieux, Julien; Sanselme, Morgane; Coquerel, Gerard Crystal Growth & Design, Vol. 16, Issue 1 https://doi.org/10.1021/acs.cgd.5b01384	journal	December 2015
Contrasting the Surface and Bulk Properties of Anhydrate and Dehydrated Hydrate Materials Yamauchi, Masahiro; Lee, Eun Hee; Otte, Andrew Crystal Growth & Design, Vol. 11, Issue 3 https://doi.org/10.1021/cg101098v	journal	January 2011
Niclosamide ethanolamine–induced mild mitochondrial uncoupling improves diabetic symptoms in mice Tao, Hanlin; Zhang, Yong; Zeng, Xiangang Nature Medicine, Vol. 20, Issue 11 https://doi.org/10.1038/nm.3699	journal	October 2014
Preparation and physicochemical properties of niclosamide anhydrate and two monohydrates van Tonder, Elsa C.; Maleka, Tshoane S. P.; Liebenberg, Wilna International Journal of Pharmaceutics, Vol. 269, Issue 2 https://doi.org/10.1016/j.ijpharm.2003.09.035	journal	January 2004
Role of isoconversional methods in varying activation energies of solid-state kinetics Khawam, Ammar; Flanagan, Douglas R. Thermochimica Acta, Vol. 429, Issue 1 https://doi.org/10.1016/j.tca.2004.11.030	journal	May 2005
Niclosamide: Beyond an antihelminthic drug Chen, Wei; Mook, Robert A.; Premont, Richard T. Cellular Signalling, Vol. 41 https://doi.org/10.1016/j.cellsig.2017.04.001	journal	January 2018
Identification of small-molecule inhibitors of Zika virus infection and induced neural cell death via a drug repurposing screen Xu, Miao; Lee, Emily M.; Wen, Zhexing Nature Medicine, Vol. 22, Issue 10 https://doi.org/10.1038/nm.4184	journal	August 2016
Plausible mechanisms of Niclosamide as an antiviral agent against COVID-19 Pindiprolu, Sai Kiran S. S.; Pindiprolu, Sai Harshini Medical Hypotheses, Vol. 140 https://doi.org/10.1016/j.mehy.2020.109765	journal	July 2020
Solid-State Kinetic Models: Basics and Mathematical Fundamentals Khawam, Ammar; Flanagan, Douglas R. The Journal of Physical Chemistry B, Vol. 110, Issue 35 https://doi.org/10.1021/jp062746a	journal	September 2006
Identifying the Stable Polymorph Early in the Drug Discovery–Development Process Miller, Jonathan M.; Collman, Benjamin M.; Greene, Landon R. Pharmaceutical Development and Technology, Vol. 10, Issue 2 https://doi.org/10.1081/PDT-54467	journal	January 2005
Formation of Isomorphic Desolvates: Creating a Molecular Vacuum Stephenson, Gregory A.; Groleau, Edward G.; Kleemann, Rita L. Journal of Pharmaceutical Sciences, Vol. 87, Issue 5 https://doi.org/10.1021/js970449z	journal	May 1998
Crystalline solids Vippagunta, Sudha R.; Brittain, Harry G.; Grant, David J. W. Advanced Drug Delivery Reviews, Vol. 48, Issue 1, p. 3-26 https://doi.org/10.1016/S0169-409X(01)00097-7	journal	May 2001
Crystal Engineering of Pharmaceutical Co-crystals: “NMR Crystallography” of Niclosamide Co-crystals Luedeker, David; Gossmann, Rebecca; Langer, Klaus Crystal Growth & Design, Vol. 16, Issue 6 https://doi.org/10.1021/acs.cgd.5b01619	journal	April 2016
Niclosamide methanol solvate and niclosamide hydrate: structure, solvent inclusion mode and implications for properties Harriss, Bethany I.; Wilson, Claire; Radosavljevic Evans, Ivana Acta Crystallographica Section C Structural Chemistry, Vol. 70, Issue 8 https://doi.org/10.1107/S2053229614015496	journal	July 2014
Influence of moisture on the crystal forms of niclosamide obtained from acetone and ethyl acetate Manek, Rahul V.; Kolling, William M. AAPS PharmSciTech, Vol. 5, Issue 1 https://doi.org/10.1208/pt050114	journal	March 2004
Antituberculosis activity of certain antifungal and antihelmintic drugs Sun, Z.; Zhang, Y. Tubercle and Lung Disease, Vol. 79, Issue 5 https://doi.org/10.1054/tuld.1999.0212	journal	September 1999
Insight into Crystallization Mechanisms of Polymorphic Hydrate Systems Tian, F.; Qu, H.; Louhi‐Kultanen, M. Chemical Engineering & Technology, Vol. 33, Issue 5 https://doi.org/10.1002/ceat.200900572	journal	April 2010
Physical transformations of the active pharmaceutical ingredient BN83495: enantiotropic and monotropic relationships. Access to several polymorphic forms by using various solvation–desolvation processes Martins, D.; Sanselme, M.; Houssin, O. CrystEngComm, Vol. 14, Issue 7 https://doi.org/10.1039/c2ce06537a	journal	January 2012
Polymorphism and Solvatomorphism 2010 Brittain, Harry G. Journal of Pharmaceutical Sciences, Vol. 101, Issue 2 https://doi.org/10.1002/jps.22788	journal	February 2012
Dual activity of niclosamide to suppress replication of integrated HIV-1 and Mycobacterium tuberculosis (Beijing) Fan, XiuZhen; Xu, Jimin; Files, Megan Tuberculosis, Vol. 116 https://doi.org/10.1016/j.tube.2019.04.008	journal	May 2019
Effect of particle size and temperature on the dehydration kinetics of trehalose dihydrate Taylor, Lynne S.; York, P. International Journal of Pharmaceutics, Vol. 167, Issue 1-2 https://doi.org/10.1016/S0378-5173(98)00065-9	journal	June 1998
Niclosamide Is a Proton Carrier and Targets Acidic Endosomes with Broad Antiviral Effects Jurgeit, Andreas; McDowell, Robert; Moese, Stefan PLoS Pathogens, Vol. 8, Issue 10 https://doi.org/10.1371/journal.ppat.1002976	journal	October 2012
Inhibition of Severe Acute Respiratory Syndrome Coronavirus Replication by Niclosamide Wu, Chang-Jer; Jan, Jia-Tsrong; Chen, Chi-Min Antimicrobial Agents and Chemotherapy, Vol. 48, Issue 7 https://doi.org/10.1128/AAC.48.7.2693-2696.2004	journal	July 2004
Comparison of the Physical and Chemical Stability of Niclosamide Crystal Forms in Aqueous Versus Nonaqueous Suspensions de Villiers, Melgardt M.; Mahlatji, Mabatane D.; van Tonder, Elsa C. Drug Development and Industrial Pharmacy, Vol. 30, Issue 6 https://doi.org/10.1081/DDC-120037489	journal	January 2004
Antihelminth Compound Niclosamide Downregulates Wnt Signaling and Elicits Antitumor Responses in Tumors with Activating APC Mutations Osada, Takuya; Chen, Minyong; Yang, Xiao Yi Cancer Research, Vol. 71, Issue 12 https://doi.org/10.1158/0008-5472.CAN-10-3978	journal	June 2011
Integrated Approach to Study the Dehydration Kinetics of Nitrofurantoin Monohydrate Koradia, Vishal; de Diego, Heidi Lopez; Elema, Michiel Ringkjøbing Journal of Pharmaceutical Sciences, Vol. 99, Issue 9 https://doi.org/10.1002/jps.22244	journal	September 2010
Structure and order in thermal dehydrations of crystalline solids Galwey, Andrew K. Thermochimica Acta, Vol. 355, Issue 1-2 https://doi.org/10.1016/S0040-6031(00)00448-2	journal	July 2000
Expanding the structural landscape of niclosamide: a highZ′ polymorph, two new solvates and monohydrate H_A Sovago, Ioana; Bond, Andrew D. Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 5 https://doi.org/10.1107/S2053229615005847	journal	April 2015
Predicting mechanical properties of crystalline materials through topological analysis Bryant, M. J.; Maloney, A. G. P.; Sykes, R. A. CrystEngComm, Vol. 20, Issue 19 https://doi.org/10.1039/C8CE00454D	journal	January 2018
Pseudopolymorphic transitions of niclosamide monitored by Raman spectroscopy Sardo, Mariana; Amado, Ana M.; Ribeiro‐Claro, Paulo J. A. Journal of Raman Spectroscopy, Vol. 39, Issue 12 https://doi.org/10.1002/jrs.2058	journal	July 2008
Basics and Applications of Solid-State Kinetics: A Pharmaceutical Perspective**The authors dedicate this review to the memory of Dr. David J.W. Grant who passed away on December 9, 2005. Dr. Grant was an internationally known authority at the University of Minnesota on the solid-state properties of drugs. He will be remembered as a kind, humble, and brilliant scholar. Khawam, Ammar; Flanagan, Douglas R. Journal of Pharmaceutical Sciences, Vol. 95, Issue 3 https://doi.org/10.1002/jps.20559	journal	March 2006
Polymorphism and molecular conformations of nicosulfuron: structure, properties and desolvation process Liu, Yu; Jia, Lina; Wu, Songgu CrystEngComm, Vol. 21, Issue 17 https://doi.org/10.1039/C8CE02074D	journal	January 2019

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