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Cocrystal polymorphs and solvates of the anti-Trypanosoma cruzi drug benznidazole with improved dissolution performance

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dc.contributor.author Bezerra, Beatriz Pinheiro
dc.contributor.author Pogoda, Dorota
dc.contributor.author Perry, Miranda L.
dc.contributor.author Vidal, Laura M. T.
dc.contributor.author Zaworotko, Michael J.
dc.contributor.author Ayala, Alejandro P.
dc.date.accessioned 2020-06-29T13:34:44Z
dc.date.issued 2020
dc.identifier.uri http://hdl.handle.net/10344/8967
dc.description peer-reviewed en_US
dc.description The full text of this article will not be available in ULIR until the embargo expires on the 15/05/2021
dc.description.abstract Benznidazole, the primary drug used in Chagas’ disease treatment, has known side effects, which may limit its widespread use. Its low solubility could negatively interfere in the bioavailability, even accentuating the toxic effects. Cocrystals have been extensively used to modify and optimize physicochemical properties, but, as single-component raw materials, they are susceptible to the phenomenon of polymorphism. In this work, we report a trimorphic cocrystal containing a 1:1 ratio of benznidazole and salicylic acid. The crystalline structures of three polymorphs were elucidated by single-crystal X-ray diffraction. Moreover, several isostructural solvates were also synthesized and analyzed. The same carboxylic acid-imidazole supramolecular heterosynthon is present in the four forms, but the main structural feature is an extended column based on amide-amide hydrogen bonds. Based on the crystalline structures, the trimorphic system was classified as conformational and packing polymorphism. Furthermore, the dissolution profiles of the stable forms were determined and shown a significant solubility improvement over the raw material. en_US
dc.language.iso eng en_US
dc.publisher American Chemical Society en_US
dc.relation.ispartofseries Crystal Growth and Design;
dc.rights © 2020 ACS This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.cgd.0c00490 en_US
dc.subject benznidazole en_US
dc.subject cocrystal en_US
dc.subject polymorphism en_US
dc.subject solvate en_US
dc.subject dissolution en_US
dc.title Cocrystal polymorphs and solvates of the anti-Trypanosoma cruzi drug benznidazole with improved dissolution performance en_US
dc.type info:eu-repo/semantics/article en_US
dc.type.supercollection all_ul_research en_US
dc.type.supercollection ul_published_reviewed en_US
dc.contributor.sponsor CAPES en_US
dc.contributor.sponsor CNPq en_US
dc.relation.projectid PR2-0101-00006.01.00/15 en_US
dc.date.embargoEndDate 2021-05-15
dc.embargo.terms 2021-05-15 en_US
dc.rights.accessrights info:eu-repo/semantics/embargoedAccess en_US


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