Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs

Autores
de Paula, Karina; Camí, Gerardo Enrique; Brusau, Elena Virginia; Narda, Griselda Edith; Ellena, Javier
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Mebendazole mesylate monohydrate, a new stable salt of mebendazole (MBZ), has been synthesized and fully characterized. It was obtained from recrystallization of MBZ forms A, B, or C in diverse solvents with the addition of methyl sulfonic acid solution. The crystal packing is first organized as a two-dimensional array consisting of rows of alternating MBZ molecules linked to columns of mesylate ions by hydrogen bonds. The three-dimensional structure is further developed by classical intermolecular interactions involving water molecules. In addition, nonclassical contacts are also found. The vibrational behavior is consistent with the crystal structure, the most important functional groups showing shifts to lower or higher frequencies in relation to the MBZ polymorphs. Thermal analysis indicates that the compound is stable up to 50◦C. Decomposition occurs in five steps. Solubility studies show that the title compound presents a significant higher performance than polymorph C.
Fil: de Paula, Karina. Universidade de Sao Paulo; Brasil
Fil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Brusau, Elena Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Ellena, Javier. Universidade de Sao Paulo; Brasil
Materia
CRYSTAL STRUCTURE
DISSOLUTION
FTIR-RAMAN SPECTROSCOPY
MEBENDAZOLE MESYLATE
SOLID STATE
THERMAL STABILITY
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:11336/2209
Acceder
id CONICETDig_808124a5a714165bf903c06fe8518a84
oai_identifier_str oai:ri.conicet.gov.ar:11336/2209
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphsde Paula, KarinaCamí, Gerardo EnriqueBrusau, Elena VirginiaNarda, Griselda EdithEllena, JavierCRYSTAL STRUCTUREDISSOLUTIONFTIR-RAMAN SPECTROSCOPYMEBENDAZOLE MESYLATESOLID STATETHERMAL STABILITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Mebendazole mesylate monohydrate, a new stable salt of mebendazole (MBZ), has been synthesized and fully characterized. It was obtained from recrystallization of MBZ forms A, B, or C in diverse solvents with the addition of methyl sulfonic acid solution. The crystal packing is first organized as a two-dimensional array consisting of rows of alternating MBZ molecules linked to columns of mesylate ions by hydrogen bonds. The three-dimensional structure is further developed by classical intermolecular interactions involving water molecules. In addition, nonclassical contacts are also found. The vibrational behavior is consistent with the crystal structure, the most important functional groups showing shifts to lower or higher frequencies in relation to the MBZ polymorphs. Thermal analysis indicates that the compound is stable up to 50◦C. Decomposition occurs in five steps. Solubility studies show that the title compound presents a significant higher performance than polymorph C.Fil: de Paula, Karina. Universidade de Sao Paulo; BrasilFil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Brusau, Elena Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Ellena, Javier. Universidade de Sao Paulo; BrasilJohn Wiley & Sons2013-07-29info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2209de Paula, Karina; Camí, Gerardo Enrique; Brusau, Elena Virginia; Narda, Griselda Edith; Ellena, Javier; Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs; John Wiley & Sons; Journal of Pharmaceutical Sciences; 102; 10; 29-7-2013; 3528-35381520-6017enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jps.23658/abstractinfo:eu-repo/semantics/altIdentifier/doi/DOI:10.1002/jps.23658info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:35:59Zoai:ri.conicet.gov.ar:11336/2209instacron: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 09:35:59.409CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
title Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
spellingShingle Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
de Paula, Karina
CRYSTAL STRUCTURE
DISSOLUTION
FTIR-RAMAN SPECTROSCOPY
MEBENDAZOLE MESYLATE
SOLID STATE
THERMAL STABILITY
title_short Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
title_full Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
title_fullStr Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
title_full_unstemmed Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
title_sort Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs
dc.creator.none.fl_str_mv de Paula, Karina
Camí, Gerardo Enrique
Brusau, Elena Virginia
Narda, Griselda Edith
Ellena, Javier
author de Paula, Karina
author_facet de Paula, Karina
Camí, Gerardo Enrique
Brusau, Elena Virginia
Narda, Griselda Edith
Ellena, Javier
author_role author
author2 Camí, Gerardo Enrique
Brusau, Elena Virginia
Narda, Griselda Edith
Ellena, Javier
author2_role author
author
author
author
dc.subject.none.fl_str_mv CRYSTAL STRUCTURE
DISSOLUTION
FTIR-RAMAN SPECTROSCOPY
MEBENDAZOLE MESYLATE
SOLID STATE
THERMAL STABILITY
topic CRYSTAL STRUCTURE
DISSOLUTION
FTIR-RAMAN SPECTROSCOPY
MEBENDAZOLE MESYLATE
SOLID STATE
THERMAL STABILITY
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 mesylate monohydrate, a new stable salt of mebendazole (MBZ), has been synthesized and fully characterized. It was obtained from recrystallization of MBZ forms A, B, or C in diverse solvents with the addition of methyl sulfonic acid solution. The crystal packing is first organized as a two-dimensional array consisting of rows of alternating MBZ molecules linked to columns of mesylate ions by hydrogen bonds. The three-dimensional structure is further developed by classical intermolecular interactions involving water molecules. In addition, nonclassical contacts are also found. The vibrational behavior is consistent with the crystal structure, the most important functional groups showing shifts to lower or higher frequencies in relation to the MBZ polymorphs. Thermal analysis indicates that the compound is stable up to 50◦C. Decomposition occurs in five steps. Solubility studies show that the title compound presents a significant higher performance than polymorph C.
Fil: de Paula, Karina. Universidade de Sao Paulo; Brasil
Fil: Camí, Gerardo Enrique. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Brusau, Elena Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Ellena, Javier. Universidade de Sao Paulo; Brasil
description Mebendazole mesylate monohydrate, a new stable salt of mebendazole (MBZ), has been synthesized and fully characterized. It was obtained from recrystallization of MBZ forms A, B, or C in diverse solvents with the addition of methyl sulfonic acid solution. The crystal packing is first organized as a two-dimensional array consisting of rows of alternating MBZ molecules linked to columns of mesylate ions by hydrogen bonds. The three-dimensional structure is further developed by classical intermolecular interactions involving water molecules. In addition, nonclassical contacts are also found. The vibrational behavior is consistent with the crystal structure, the most important functional groups showing shifts to lower or higher frequencies in relation to the MBZ polymorphs. Thermal analysis indicates that the compound is stable up to 50◦C. Decomposition occurs in five steps. Solubility studies show that the title compound presents a significant higher performance than polymorph C.
publishDate 2013
dc.date.none.fl_str_mv 2013-07-29
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/11336/2209
de Paula, Karina; Camí, Gerardo Enrique; Brusau, Elena Virginia; Narda, Griselda Edith; Ellena, Javier; Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs; John Wiley & Sons; Journal of Pharmaceutical Sciences; 102; 10; 29-7-2013; 3528-3538
1520-6017
url http://hdl.handle.net/11336/2209
identifier_str_mv de Paula, Karina; Camí, Gerardo Enrique; Brusau, Elena Virginia; Narda, Griselda Edith; Ellena, Javier; Mebendazole Mesylate Monohydrate: A New Route to Improve the Solubility of Mebendazole Polymorphs; John Wiley & Sons; Journal of Pharmaceutical Sciences; 102; 10; 29-7-2013; 3528-3538
1520-6017
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jps.23658/abstract
info:eu-repo/semantics/altIdentifier/doi/DOI:10.1002/jps.23658
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
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
_version_ 1844613125582618624
score 13.070432

Publicaciones similares