Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride

Autores
Brusau, Elena Virginia; Camí, Gerardo Enrique; Narda, Griselda Edith; Cuffini, Silvia Lucia; Ayala, A. P.; Ellena, J.
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Mebendazole hydrochloride [(5‐benzoyl‐1H‐benzimidazole‐2‐yl)‐carbamic acid methyl ester hydrochloride, MBZ·HCl], a new stable salt of mebendazole (MBZ), has been synthesized and characterized. It can easily be obtained from recrystallization of forms A, B, or C of MBZ in diverse solvents with the addition of hydrochloric acid solution. Crystallographic data reveals that the particular conformation adopted by the carbamic group contributes to the stability of the network. The crystal packing is stabilized by the presence of three N–H…Cl intermolecular interactions that form chains along the b axis. The XRD analyses of the three crystalline habits found in the crystallization process (square‐based pyramids, pseudohexagonal plates, and prismatic) show equivalent diffraction patterns. The vibrational behavior is consistent with crystal structure. The most important functional groups show shifts to lower or higher frequencies in relation to the MBZ polymorphs. The thermal study on MBZ·HCl indicates that the compound is stable up to 160°C approximately. Decomposition occurs in four steps. In the first step the HCl group is eliminated, and after that the remaining MBZ polymorph A decomposes in three steps, as happens with polymorphs B and C.
Fil: Brusau, Elena Virginia. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; Argentina
Fil: Ayala, A. P.. Universidade Federal do Ceara; Brasil
Fil: Ellena, J.. Universidade de Sao Paulo; Brasil
Materia
Mebendazole hydrochloride
Polymorphism
Salt formation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/242252
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/242252
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis and Characterization of a New Mebendazole Salt: Mebendazole HydrochlorideBrusau, Elena VirginiaCamí, Gerardo EnriqueNarda, Griselda EdithCuffini, Silvia LuciaAyala, A. P.Ellena, J.Mebendazole hydrochloridePolymorphismSalt formationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Mebendazole hydrochloride [(5‐benzoyl‐1H‐benzimidazole‐2‐yl)‐carbamic acid methyl ester hydrochloride, MBZ·HCl], a new stable salt of mebendazole (MBZ), has been synthesized and characterized. It can easily be obtained from recrystallization of forms A, B, or C of MBZ in diverse solvents with the addition of hydrochloric acid solution. Crystallographic data reveals that the particular conformation adopted by the carbamic group contributes to the stability of the network. The crystal packing is stabilized by the presence of three N–H…Cl intermolecular interactions that form chains along the b axis. The XRD analyses of the three crystalline habits found in the crystallization process (square‐based pyramids, pseudohexagonal plates, and prismatic) show equivalent diffraction patterns. The vibrational behavior is consistent with crystal structure. The most important functional groups show shifts to lower or higher frequencies in relation to the MBZ polymorphs. The thermal study on MBZ·HCl indicates that the compound is stable up to 160°C approximately. Decomposition occurs in four steps. In the first step the HCl group is eliminated, and after that the remaining MBZ polymorph A decomposes in three steps, as happens with polymorphs B and C.Fil: Brusau, Elena Virginia. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; ArgentinaFil: Ayala, A. P.. Universidade Federal do Ceara; BrasilFil: Ellena, J.. Universidade de Sao Paulo; BrasilJohn Wiley & Sons2008-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/242252Brusau, Elena Virginia; Camí, Gerardo Enrique; Narda, Griselda Edith; Cuffini, Silvia Lucia; Ayala, A. P.; et al.; Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride; John Wiley & Sons; Journal of Pharmaceutical Sciences; 97; 1; 1-2008; 542-5520022-3549CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0022354916324625info:eu-repo/semantics/altIdentifier/doi/10.1002/jps.21164info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:52:30Zoai:ri.conicet.gov.ar:11336/242252instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:52:30.566CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
title Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
spellingShingle Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
Brusau, Elena Virginia
Mebendazole hydrochloride
Polymorphism
Salt formation
title_short Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
title_full Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
title_fullStr Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
title_full_unstemmed Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
title_sort Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride
dc.creator.none.fl_str_mv Brusau, Elena Virginia
Camí, Gerardo Enrique
Narda, Griselda Edith
Cuffini, Silvia Lucia
Ayala, A. P.
Ellena, J.
author Brusau, Elena Virginia
author_facet Brusau, Elena Virginia
Camí, Gerardo Enrique
Narda, Griselda Edith
Cuffini, Silvia Lucia
Ayala, A. P.
Ellena, J.
author_role author
author2 Camí, Gerardo Enrique
Narda, Griselda Edith
Cuffini, Silvia Lucia
Ayala, A. P.
Ellena, J.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Mebendazole hydrochloride
Polymorphism
Salt formation
topic Mebendazole hydrochloride
Polymorphism
Salt formation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Mebendazole hydrochloride [(5‐benzoyl‐1H‐benzimidazole‐2‐yl)‐carbamic acid methyl ester hydrochloride, MBZ·HCl], a new stable salt of mebendazole (MBZ), has been synthesized and characterized. It can easily be obtained from recrystallization of forms A, B, or C of MBZ in diverse solvents with the addition of hydrochloric acid solution. Crystallographic data reveals that the particular conformation adopted by the carbamic group contributes to the stability of the network. The crystal packing is stabilized by the presence of three N–H…Cl intermolecular interactions that form chains along the b axis. The XRD analyses of the three crystalline habits found in the crystallization process (square‐based pyramids, pseudohexagonal plates, and prismatic) show equivalent diffraction patterns. The vibrational behavior is consistent with crystal structure. The most important functional groups show shifts to lower or higher frequencies in relation to the MBZ polymorphs. The thermal study on MBZ·HCl indicates that the compound is stable up to 160°C approximately. Decomposition occurs in four steps. In the first step the HCl group is eliminated, and after that the remaining MBZ polymorph A decomposes in three steps, as happens with polymorphs B and C.
Fil: Brusau, Elena Virginia. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; Argentina
Fil: Ayala, A. P.. Universidade Federal do Ceara; Brasil
Fil: Ellena, J.. Universidade de Sao Paulo; Brasil
description Mebendazole hydrochloride [(5‐benzoyl‐1H‐benzimidazole‐2‐yl)‐carbamic acid methyl ester hydrochloride, MBZ·HCl], a new stable salt of mebendazole (MBZ), has been synthesized and characterized. It can easily be obtained from recrystallization of forms A, B, or C of MBZ in diverse solvents with the addition of hydrochloric acid solution. Crystallographic data reveals that the particular conformation adopted by the carbamic group contributes to the stability of the network. The crystal packing is stabilized by the presence of three N–H…Cl intermolecular interactions that form chains along the b axis. The XRD analyses of the three crystalline habits found in the crystallization process (square‐based pyramids, pseudohexagonal plates, and prismatic) show equivalent diffraction patterns. The vibrational behavior is consistent with crystal structure. The most important functional groups show shifts to lower or higher frequencies in relation to the MBZ polymorphs. The thermal study on MBZ·HCl indicates that the compound is stable up to 160°C approximately. Decomposition occurs in four steps. In the first step the HCl group is eliminated, and after that the remaining MBZ polymorph A decomposes in three steps, as happens with polymorphs B and C.
publishDate 2008
dc.date.none.fl_str_mv 2008-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/242252
Brusau, Elena Virginia; Camí, Gerardo Enrique; Narda, Griselda Edith; Cuffini, Silvia Lucia; Ayala, A. P.; et al.; Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride; John Wiley & Sons; Journal of Pharmaceutical Sciences; 97; 1; 1-2008; 542-552
0022-3549
CONICET Digital
CONICET
url http://hdl.handle.net/11336/242252
identifier_str_mv Brusau, Elena Virginia; Camí, Gerardo Enrique; Narda, Griselda Edith; Cuffini, Silvia Lucia; Ayala, A. P.; et al.; Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride; John Wiley & Sons; Journal of Pharmaceutical Sciences; 97; 1; 1-2008; 542-552
0022-3549
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0022354916324625
info:eu-repo/semantics/altIdentifier/doi/10.1002/jps.21164
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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