Conformational polymorphism of the antidiabetic drug chlorpropamide

Autores
Ayala, A. P.; Caetano, M. W. C.; Honorato, S. B.; Mendes Filho, J.; Siesler, H. W.; Faudone, Sonia Nerina; Cuffini, Silvia Lucia; Martins, F. T.; Da Silva, C. C. P.; Ellena, J.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this paper, the main features of Raman spectroscopy, one of the first choice methods in the study of polymorphism in pharmaceuticals, are presented taking chlorpropamide as a case of study. The antidiabetic drug chlorpropamide (1-[4- chlorobenzenesulphonyl]-3-propyl urea),which belongs to the sulfonylurea class, is known to exhibit, at least, six polymorphic phases. These forms are characterized not onlyby variations in their molecular packingbut also intheir molecular conformation. In this study, the polymorphism of chlorpropamide is discussed on the basis of Raman scattering measurements and quantum mechanical calculations. The main spectroscopic features that fingerprint the crystalline forms are correlated with the corresponding crystalline structures. Using a theoretical approach on the energy dependence of the conformers, simulated molecular torsion angles are plotted versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide.
Fil: Ayala, A. P.. Universidade de Sao Paulo; Brasil. Universidade Estadual do Ceará; Brasil
Fil: Caetano, M. W. C.. Universidade Estadual do Ceará; Brasil
Fil: Honorato, S. B.. Universidade Estadual do Ceará; Brasil
Fil: Mendes Filho, J.. Universidade Estadual do Ceará; Brasil
Fil: Siesler, H. W.. Universitat Essen; Alemania
Fil: Faudone, Sonia Nerina. Universidade Federal de Santa Catarina; Brasil
Fil: Cuffini, Silvia Lucia. Universidade Federal de Santa Catarina; Brasil. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Martins, F. T.. Universidade de Sao Paulo; Brasil
Fil: Da Silva, C. C. P.. Universidade de Sao Paulo; Brasil
Fil: Ellena, J.. Universidade de Sao Paulo; Brasil
Materia
CHLORPROPAMIDE
DFT
POLYMORPHISM
RAMAN SPECTROSCOPY
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:11336/193595
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/193595
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Conformational polymorphism of the antidiabetic drug chlorpropamideAyala, A. P.Caetano, M. W. C.Honorato, S. B.Mendes Filho, J.Siesler, H. W.Faudone, Sonia NerinaCuffini, Silvia LuciaMartins, F. T.Da Silva, C. C. P.Ellena, J.CHLORPROPAMIDEDFTPOLYMORPHISMRAMAN SPECTROSCOPYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this paper, the main features of Raman spectroscopy, one of the first choice methods in the study of polymorphism in pharmaceuticals, are presented taking chlorpropamide as a case of study. The antidiabetic drug chlorpropamide (1-[4- chlorobenzenesulphonyl]-3-propyl urea),which belongs to the sulfonylurea class, is known to exhibit, at least, six polymorphic phases. These forms are characterized not onlyby variations in their molecular packingbut also intheir molecular conformation. In this study, the polymorphism of chlorpropamide is discussed on the basis of Raman scattering measurements and quantum mechanical calculations. The main spectroscopic features that fingerprint the crystalline forms are correlated with the corresponding crystalline structures. Using a theoretical approach on the energy dependence of the conformers, simulated molecular torsion angles are plotted versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide.Fil: Ayala, A. P.. Universidade de Sao Paulo; Brasil. Universidade Estadual do Ceará; BrasilFil: Caetano, M. W. C.. Universidade Estadual do Ceará; BrasilFil: Honorato, S. B.. Universidade Estadual do Ceará; BrasilFil: Mendes Filho, J.. Universidade Estadual do Ceará; BrasilFil: Siesler, H. W.. Universitat Essen; AlemaniaFil: Faudone, Sonia Nerina. Universidade Federal de Santa Catarina; BrasilFil: Cuffini, Silvia Lucia. Universidade Federal de Santa Catarina; Brasil. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Martins, F. T.. Universidade de Sao Paulo; BrasilFil: Da Silva, C. C. P.. Universidade de Sao Paulo; BrasilFil: Ellena, J.. Universidade de Sao Paulo; BrasilJohn Wiley & Sons Ltd2011-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/193595Ayala, A. P.; Caetano, M. W. C.; Honorato, S. B.; Mendes Filho, J.; Siesler, H. W.; et al.; Conformational polymorphism of the antidiabetic drug chlorpropamide; John Wiley & Sons Ltd; Journal Of Raman Spectroscopy; 43; 2; 7-2011; 263-2720377-0486CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/full/10.1002/jrs.3012info:eu-repo/semantics/altIdentifier/doi/10.1002/jrs.3012info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:52:03Zoai:ri.conicet.gov.ar:11336/193595instacron: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 09:52:03.326CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Conformational polymorphism of the antidiabetic drug chlorpropamide
title Conformational polymorphism of the antidiabetic drug chlorpropamide
spellingShingle Conformational polymorphism of the antidiabetic drug chlorpropamide
Ayala, A. P.
CHLORPROPAMIDE
DFT
POLYMORPHISM
RAMAN SPECTROSCOPY
title_short Conformational polymorphism of the antidiabetic drug chlorpropamide
title_full Conformational polymorphism of the antidiabetic drug chlorpropamide
title_fullStr Conformational polymorphism of the antidiabetic drug chlorpropamide
title_full_unstemmed Conformational polymorphism of the antidiabetic drug chlorpropamide
title_sort Conformational polymorphism of the antidiabetic drug chlorpropamide
dc.creator.none.fl_str_mv Ayala, A. P.
Caetano, M. W. C.
Honorato, S. B.
Mendes Filho, J.
Siesler, H. W.
Faudone, Sonia Nerina
Cuffini, Silvia Lucia
Martins, F. T.
Da Silva, C. C. P.
Ellena, J.
author Ayala, A. P.
author_facet Ayala, A. P.
Caetano, M. W. C.
Honorato, S. B.
Mendes Filho, J.
Siesler, H. W.
Faudone, Sonia Nerina
Cuffini, Silvia Lucia
Martins, F. T.
Da Silva, C. C. P.
Ellena, J.
author_role author
author2 Caetano, M. W. C.
Honorato, S. B.
Mendes Filho, J.
Siesler, H. W.
Faudone, Sonia Nerina
Cuffini, Silvia Lucia
Martins, F. T.
Da Silva, C. C. P.
Ellena, J.
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv CHLORPROPAMIDE
DFT
POLYMORPHISM
RAMAN SPECTROSCOPY
topic CHLORPROPAMIDE
DFT
POLYMORPHISM
RAMAN SPECTROSCOPY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this paper, the main features of Raman spectroscopy, one of the first choice methods in the study of polymorphism in pharmaceuticals, are presented taking chlorpropamide as a case of study. The antidiabetic drug chlorpropamide (1-[4- chlorobenzenesulphonyl]-3-propyl urea),which belongs to the sulfonylurea class, is known to exhibit, at least, six polymorphic phases. These forms are characterized not onlyby variations in their molecular packingbut also intheir molecular conformation. In this study, the polymorphism of chlorpropamide is discussed on the basis of Raman scattering measurements and quantum mechanical calculations. The main spectroscopic features that fingerprint the crystalline forms are correlated with the corresponding crystalline structures. Using a theoretical approach on the energy dependence of the conformers, simulated molecular torsion angles are plotted versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide.
Fil: Ayala, A. P.. Universidade de Sao Paulo; Brasil. Universidade Estadual do Ceará; Brasil
Fil: Caetano, M. W. C.. Universidade Estadual do Ceará; Brasil
Fil: Honorato, S. B.. Universidade Estadual do Ceará; Brasil
Fil: Mendes Filho, J.. Universidade Estadual do Ceará; Brasil
Fil: Siesler, H. W.. Universitat Essen; Alemania
Fil: Faudone, Sonia Nerina. Universidade Federal de Santa Catarina; Brasil
Fil: Cuffini, Silvia Lucia. Universidade Federal de Santa Catarina; Brasil. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Martins, F. T.. Universidade de Sao Paulo; Brasil
Fil: Da Silva, C. C. P.. Universidade de Sao Paulo; Brasil
Fil: Ellena, J.. Universidade de Sao Paulo; Brasil
description In this paper, the main features of Raman spectroscopy, one of the first choice methods in the study of polymorphism in pharmaceuticals, are presented taking chlorpropamide as a case of study. The antidiabetic drug chlorpropamide (1-[4- chlorobenzenesulphonyl]-3-propyl urea),which belongs to the sulfonylurea class, is known to exhibit, at least, six polymorphic phases. These forms are characterized not onlyby variations in their molecular packingbut also intheir molecular conformation. In this study, the polymorphism of chlorpropamide is discussed on the basis of Raman scattering measurements and quantum mechanical calculations. The main spectroscopic features that fingerprint the crystalline forms are correlated with the corresponding crystalline structures. Using a theoretical approach on the energy dependence of the conformers, simulated molecular torsion angles are plotted versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide versus the formation energy,which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide.
publishDate 2011
dc.date.none.fl_str_mv 2011-07
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/11336/193595
Ayala, A. P.; Caetano, M. W. C.; Honorato, S. B.; Mendes Filho, J.; Siesler, H. W.; et al.; Conformational polymorphism of the antidiabetic drug chlorpropamide; John Wiley & Sons Ltd; Journal Of Raman Spectroscopy; 43; 2; 7-2011; 263-272
0377-0486
CONICET Digital
CONICET
url http://hdl.handle.net/11336/193595
identifier_str_mv Ayala, A. P.; Caetano, M. W. C.; Honorato, S. B.; Mendes Filho, J.; Siesler, H. W.; et al.; Conformational polymorphism of the antidiabetic drug chlorpropamide; John Wiley & Sons Ltd; Journal Of Raman Spectroscopy; 43; 2; 7-2011; 263-272
0377-0486
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://analyticalsciencejournals.onlinelibrary.wiley.com/doi/full/10.1002/jrs.3012
info:eu-repo/semantics/altIdentifier/doi/10.1002/jrs.3012
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 Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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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