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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/242252
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T09:53:23Zoai: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:34982025-09-03 09:53:23.816CONICET 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 |
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CONICET Digital (CONICET) |
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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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1842269222614335488 |
score |
13.13397 |