Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions
- Autores
- Gaztañaga, Pablo Ernesto; Baggio, Ricardo Fortunato; Vega, Daniel Roberto
- Año de publicación
- 2019
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Crystallographic, thermal and stability analyses are presented of three different anhydrated forms of bendamustine hydrochloride [(I), (III) and (IV)] and a fourth, monohydrated one (II). Since form (I) presents the higher melting point and the higher heat of fusion, according to the 'heat of fusion' rule it should be the most stable in thermodynamic terms [Burger & Ramberger (1979). Mikrochim. Acta, 72, 259-271], though it is unstable in high-humidity conditions. The monohydrate structure (II), in turn, dehydrates by heating and topotactically transform into anhydrate (III). This latter form appears as less stable than anhydrate (I), to which it is linked via a monotropic relationship. For these three different forms, the crystal structure has been determined by single crystal X-ray diffraction. The crystal structures and molecular conformations of forms (II) and (III) are quite similar, as expected from the topotactic transformation linking them; furthermore, under high-humidity conditions, form (III) shows changes compatible with a transformation into form (II) within 24 h. The crystal structure of form (I) is different from the other two. The remaining polymorphic form (IV) could only be obtained as a powder, from which its crystalline structure could not be determined. The relative thermodynamic stability of the different crystalline forms was determined by differential scanning calorimetry and thermogravimetrical studies, and their stability under different humidity conditions analysed.
Fil: Gaztañaga, Pablo Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Fil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina - Materia
-
BENDAMUSTINE HYDROCHLORIDE
CRYSTAL STRUCTURE
POLYMORPHISM
SINGLE-CRYSTAL X-RAY DIFFRACTION - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/175148
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Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditionsGaztañaga, Pablo ErnestoBaggio, Ricardo FortunatoVega, Daniel RobertoBENDAMUSTINE HYDROCHLORIDECRYSTAL STRUCTUREPOLYMORPHISMSINGLE-CRYSTAL X-RAY DIFFRACTIONhttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1Crystallographic, thermal and stability analyses are presented of three different anhydrated forms of bendamustine hydrochloride [(I), (III) and (IV)] and a fourth, monohydrated one (II). Since form (I) presents the higher melting point and the higher heat of fusion, according to the 'heat of fusion' rule it should be the most stable in thermodynamic terms [Burger & Ramberger (1979). Mikrochim. Acta, 72, 259-271], though it is unstable in high-humidity conditions. The monohydrate structure (II), in turn, dehydrates by heating and topotactically transform into anhydrate (III). This latter form appears as less stable than anhydrate (I), to which it is linked via a monotropic relationship. For these three different forms, the crystal structure has been determined by single crystal X-ray diffraction. The crystal structures and molecular conformations of forms (II) and (III) are quite similar, as expected from the topotactic transformation linking them; furthermore, under high-humidity conditions, form (III) shows changes compatible with a transformation into form (II) within 24 h. The crystal structure of form (I) is different from the other two. The remaining polymorphic form (IV) could only be obtained as a powder, from which its crystalline structure could not be determined. The relative thermodynamic stability of the different crystalline forms was determined by differential scanning calorimetry and thermogravimetrical studies, and their stability under different humidity conditions analysed.Fil: Gaztañaga, Pablo Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaFil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; ArgentinaInternational Union of Crystallography2019-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/175148Gaztañaga, Pablo Ernesto; Baggio, Ricardo Fortunato; Vega, Daniel Roberto; Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions; International Union of Crystallography; Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials; 75; 10-2019; 933-9412052-5206CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2052520619010837info:eu-repo/semantics/altIdentifier/doi/10.1107/S2052520619010837info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:51:03Zoai:ri.conicet.gov.ar:11336/175148instacron: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 09:51:04.152CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
title |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
spellingShingle |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions Gaztañaga, Pablo Ernesto BENDAMUSTINE HYDROCHLORIDE CRYSTAL STRUCTURE POLYMORPHISM SINGLE-CRYSTAL X-RAY DIFFRACTION |
title_short |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
title_full |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
title_fullStr |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
title_full_unstemmed |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
title_sort |
Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions |
dc.creator.none.fl_str_mv |
Gaztañaga, Pablo Ernesto Baggio, Ricardo Fortunato Vega, Daniel Roberto |
author |
Gaztañaga, Pablo Ernesto |
author_facet |
Gaztañaga, Pablo Ernesto Baggio, Ricardo Fortunato Vega, Daniel Roberto |
author_role |
author |
author2 |
Baggio, Ricardo Fortunato Vega, Daniel Roberto |
author2_role |
author author |
dc.subject.none.fl_str_mv |
BENDAMUSTINE HYDROCHLORIDE CRYSTAL STRUCTURE POLYMORPHISM SINGLE-CRYSTAL X-RAY DIFFRACTION |
topic |
BENDAMUSTINE HYDROCHLORIDE CRYSTAL STRUCTURE POLYMORPHISM SINGLE-CRYSTAL X-RAY DIFFRACTION |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.3 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Crystallographic, thermal and stability analyses are presented of three different anhydrated forms of bendamustine hydrochloride [(I), (III) and (IV)] and a fourth, monohydrated one (II). Since form (I) presents the higher melting point and the higher heat of fusion, according to the 'heat of fusion' rule it should be the most stable in thermodynamic terms [Burger & Ramberger (1979). Mikrochim. Acta, 72, 259-271], though it is unstable in high-humidity conditions. The monohydrate structure (II), in turn, dehydrates by heating and topotactically transform into anhydrate (III). This latter form appears as less stable than anhydrate (I), to which it is linked via a monotropic relationship. For these three different forms, the crystal structure has been determined by single crystal X-ray diffraction. The crystal structures and molecular conformations of forms (II) and (III) are quite similar, as expected from the topotactic transformation linking them; furthermore, under high-humidity conditions, form (III) shows changes compatible with a transformation into form (II) within 24 h. The crystal structure of form (I) is different from the other two. The remaining polymorphic form (IV) could only be obtained as a powder, from which its crystalline structure could not be determined. The relative thermodynamic stability of the different crystalline forms was determined by differential scanning calorimetry and thermogravimetrical studies, and their stability under different humidity conditions analysed. Fil: Gaztañaga, Pablo Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina Fil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina |
description |
Crystallographic, thermal and stability analyses are presented of three different anhydrated forms of bendamustine hydrochloride [(I), (III) and (IV)] and a fourth, monohydrated one (II). Since form (I) presents the higher melting point and the higher heat of fusion, according to the 'heat of fusion' rule it should be the most stable in thermodynamic terms [Burger & Ramberger (1979). Mikrochim. Acta, 72, 259-271], though it is unstable in high-humidity conditions. The monohydrate structure (II), in turn, dehydrates by heating and topotactically transform into anhydrate (III). This latter form appears as less stable than anhydrate (I), to which it is linked via a monotropic relationship. For these three different forms, the crystal structure has been determined by single crystal X-ray diffraction. The crystal structures and molecular conformations of forms (II) and (III) are quite similar, as expected from the topotactic transformation linking them; furthermore, under high-humidity conditions, form (III) shows changes compatible with a transformation into form (II) within 24 h. The crystal structure of form (I) is different from the other two. The remaining polymorphic form (IV) could only be obtained as a powder, from which its crystalline structure could not be determined. The relative thermodynamic stability of the different crystalline forms was determined by differential scanning calorimetry and thermogravimetrical studies, and their stability under different humidity conditions analysed. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10 |
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/11336/175148 Gaztañaga, Pablo Ernesto; Baggio, Ricardo Fortunato; Vega, Daniel Roberto; Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions; International Union of Crystallography; Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials; 75; 10-2019; 933-941 2052-5206 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/175148 |
identifier_str_mv |
Gaztañaga, Pablo Ernesto; Baggio, Ricardo Fortunato; Vega, Daniel Roberto; Polymorphic forms of bendamustine hydrochloride: crystal structure, thermal properties and stability at ambient conditions; International Union of Crystallography; Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials; 75; 10-2019; 933-941 2052-5206 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2052520619010837 info:eu-repo/semantics/altIdentifier/doi/10.1107/S2052520619010837 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
International Union of Crystallography |
publisher.none.fl_str_mv |
International Union of Crystallography |
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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1842269070820376576 |
score |
13.13397 |