Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine

Autores
Russo, Marcos Guillermo; Brusau, Elena Virginia; Ellena, Javier; Narda, Griselda Edith
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Famotidine (FMT), a histamine H2-receptor antagonist, is a drug commonly used in treatments of gastroesophageal diseases that presents solid-state polymorphism (A and B forms), the marketed form being the metastable polymorph B. A new stable salt was obtained by combination of FMT and maleic acid as coformer. FMT maleate (FMT-MLT) was prepared either by solvent evaporation or comilling methods. Single-crystal X-ray diffraction reveals that (FMT)+ in FMT-MLT adopts an extended conformation that is stabilized by classical and nonclassical H-bonds. The three-dimensional packing consists of tapes along the axis b that further develop a columnar array based on H-bonds involving (FMT)+ side chain. Nonconventional ?stacking interactions between adjacent tapes were also identified. Fourier transform infrared, differential scanning calorimetry, thermogravimetric analysis, polarized light thermal microscopy, and scanning electronmicroscopy were employed to characterize the multicomponent complex. According to the solubility values in water and simulated gastric fluid, FMT-MLT exhibits such a performance that improves on the solubility of the commercially available polymorph. Finally, the higher stability of FMT-MLT regarding both FMT forms, as well as its easy preparation from either A or B forms or a mixture of them, also allows to consider this salt as a valuable alternative to avoid the polymorphism issue in marketed formulations containing FMT
Fil: Russo, Marcos Guillermo. 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: Ellena, Javier. Universidade de Sao Paulo; Brasil
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones En Tecnología Química; Argentina
Materia
Crystal Structure
Solid State
Thermal Analysis
Physicochemical Properties
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:11336/5854
Acceder
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spelling Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in FamotidineRusso, Marcos GuillermoBrusau, Elena VirginiaEllena, JavierNarda, Griselda EdithCrystal StructureSolid StateThermal AnalysisPhysicochemical Propertieshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Famotidine (FMT), a histamine H2-receptor antagonist, is a drug commonly used in treatments of gastroesophageal diseases that presents solid-state polymorphism (A and B forms), the marketed form being the metastable polymorph B. A new stable salt was obtained by combination of FMT and maleic acid as coformer. FMT maleate (FMT-MLT) was prepared either by solvent evaporation or comilling methods. Single-crystal X-ray diffraction reveals that (FMT)+ in FMT-MLT adopts an extended conformation that is stabilized by classical and nonclassical H-bonds. The three-dimensional packing consists of tapes along the axis b that further develop a columnar array based on H-bonds involving (FMT)+ side chain. Nonconventional ?stacking interactions between adjacent tapes were also identified. Fourier transform infrared, differential scanning calorimetry, thermogravimetric analysis, polarized light thermal microscopy, and scanning electronmicroscopy were employed to characterize the multicomponent complex. According to the solubility values in water and simulated gastric fluid, FMT-MLT exhibits such a performance that improves on the solubility of the commercially available polymorph. Finally, the higher stability of FMT-MLT regarding both FMT forms, as well as its easy preparation from either A or B forms or a mixture of them, also allows to consider this salt as a valuable alternative to avoid the polymorphism issue in marketed formulations containing FMTFil: Russo, Marcos Guillermo. 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: Ellena, Javier. Universidade de Sao Paulo; BrasilFil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones En Tecnología Química; ArgentinaWiley2014-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5854Russo, Marcos Guillermo; Brusau, Elena Virginia; Ellena, Javier; Narda, Griselda Edith; Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine; Wiley; Journal of Pharmaceutical Sciences; 103; 11; 9-2014; 3754-37630022-3549enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jps.24196/abstractinfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1002/jps.24196info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:21:17Zoai:ri.conicet.gov.ar:11336/5854instacron: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:34982025-10-15 14:21:17.321CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
title Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
spellingShingle Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
Russo, Marcos Guillermo
Crystal Structure
Solid State
Thermal Analysis
Physicochemical Properties
title_short Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
title_full Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
title_fullStr Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
title_full_unstemmed Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
title_sort Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine
dc.creator.none.fl_str_mv Russo, Marcos Guillermo
Brusau, Elena Virginia
Ellena, Javier
Narda, Griselda Edith
author Russo, Marcos Guillermo
author_facet Russo, Marcos Guillermo
Brusau, Elena Virginia
Ellena, Javier
Narda, Griselda Edith
author_role author
author2 Brusau, Elena Virginia
Ellena, Javier
Narda, Griselda Edith
author2_role author
author
author
dc.subject.none.fl_str_mv Crystal Structure
Solid State
Thermal Analysis
Physicochemical Properties
topic Crystal Structure
Solid State
Thermal Analysis
Physicochemical Properties
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Famotidine (FMT), a histamine H2-receptor antagonist, is a drug commonly used in treatments of gastroesophageal diseases that presents solid-state polymorphism (A and B forms), the marketed form being the metastable polymorph B. A new stable salt was obtained by combination of FMT and maleic acid as coformer. FMT maleate (FMT-MLT) was prepared either by solvent evaporation or comilling methods. Single-crystal X-ray diffraction reveals that (FMT)+ in FMT-MLT adopts an extended conformation that is stabilized by classical and nonclassical H-bonds. The three-dimensional packing consists of tapes along the axis b that further develop a columnar array based on H-bonds involving (FMT)+ side chain. Nonconventional ?stacking interactions between adjacent tapes were also identified. Fourier transform infrared, differential scanning calorimetry, thermogravimetric analysis, polarized light thermal microscopy, and scanning electronmicroscopy were employed to characterize the multicomponent complex. According to the solubility values in water and simulated gastric fluid, FMT-MLT exhibits such a performance that improves on the solubility of the commercially available polymorph. Finally, the higher stability of FMT-MLT regarding both FMT forms, as well as its easy preparation from either A or B forms or a mixture of them, also allows to consider this salt as a valuable alternative to avoid the polymorphism issue in marketed formulations containing FMT
Fil: Russo, Marcos Guillermo. 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: Ellena, Javier. Universidade de Sao Paulo; Brasil
Fil: Narda, Griselda Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones En Tecnología Química; Argentina
description Famotidine (FMT), a histamine H2-receptor antagonist, is a drug commonly used in treatments of gastroesophageal diseases that presents solid-state polymorphism (A and B forms), the marketed form being the metastable polymorph B. A new stable salt was obtained by combination of FMT and maleic acid as coformer. FMT maleate (FMT-MLT) was prepared either by solvent evaporation or comilling methods. Single-crystal X-ray diffraction reveals that (FMT)+ in FMT-MLT adopts an extended conformation that is stabilized by classical and nonclassical H-bonds. The three-dimensional packing consists of tapes along the axis b that further develop a columnar array based on H-bonds involving (FMT)+ side chain. Nonconventional ?stacking interactions between adjacent tapes were also identified. Fourier transform infrared, differential scanning calorimetry, thermogravimetric analysis, polarized light thermal microscopy, and scanning electronmicroscopy were employed to characterize the multicomponent complex. According to the solubility values in water and simulated gastric fluid, FMT-MLT exhibits such a performance that improves on the solubility of the commercially available polymorph. Finally, the higher stability of FMT-MLT regarding both FMT forms, as well as its easy preparation from either A or B forms or a mixture of them, also allows to consider this salt as a valuable alternative to avoid the polymorphism issue in marketed formulations containing FMT
publishDate 2014
dc.date.none.fl_str_mv 2014-09
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/11336/5854
Russo, Marcos Guillermo; Brusau, Elena Virginia; Ellena, Javier; Narda, Griselda Edith; Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine; Wiley; Journal of Pharmaceutical Sciences; 103; 11; 9-2014; 3754-3763
0022-3549
url http://hdl.handle.net/11336/5854
identifier_str_mv Russo, Marcos Guillermo; Brusau, Elena Virginia; Ellena, Javier; Narda, Griselda Edith; Solid-State Supramolecular Synthesis Based on the N–H...O Heterosynthon: An Approach to Solve the Polymorphism Problem in Famotidine; Wiley; Journal of Pharmaceutical Sciences; 103; 11; 9-2014; 3754-3763
0022-3549
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.24196/abstract
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1002/jps.24196
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 Wiley
publisher.none.fl_str_mv Wiley
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 13.221938

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