Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties

Autores
Fandaruff, Cinira; Rauber, Gabriela S.; Araya Sibaja, Andrea Mariela; Pereira, Rafael N.; De Campos, Carlos E. M.; Rocha, Helvécio V. A.; Monti, Gustavo Alberto; Malaspina, Thaciana; Silva, Marcos A. S.; Cuffini, Silvia Lucia
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Polymorphs, cocrystals, solvates, and hydrates have been reported for efavirenz (EFV), which is part of high activity antiretroviral therapy (HAART), and it is considered to be the best choice in the treatment of adults and children. However, studies about thermodynamic stability and improvement of dissolution properties have been rarely reported for the anhydrous polymorphic forms. Therefore, the aim of this work was to characterize the solid state of anhydrous polymorph I and polymorph II (herein obtained), to study the thermodynamic stability and strategies to improve the dissolution properties. In addition, techniques such as, X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), hot stage microscopy (HSM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), raman spectroscopy (RS), theoretical calculations, and solid-state nuclear magnetic resonance (ss-NMR) were used to complete this work. Thermodynamic studies showed that polymorphs I and II are enantiotropically related with the isoenergetic point between 35 and 40 °C. The EFV polymorph II showed itself to be more stable and 10-fold more soluble than polymorph I, due to modifications of morphology. Therefore, polymorph II could be an excellent candidate with significant advantages for pharmaceutical formulations.
Fil: Fandaruff, Cinira. Universidade Federal de Santa Catarina; Brasil
Fil: Rauber, Gabriela S.. Universidade Federal de Santa Catarina; Brasil
Fil: Araya Sibaja, Andrea Mariela. Universidad de Costa Rica; Costa Rica
Fil: Pereira, Rafael N.. Universidade Federal de Santa Catarina; Brasil
Fil: De Campos, Carlos E. M.. Universidade Federal de Santa Catarina; Brasil
Fil: Rocha, Helvécio V. A.. Fundación Oswaldo Cruz; Brasil
Fil: Monti, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; Argentina
Fil: Malaspina, Thaciana. Universidade de Sao Paulo; Brasil
Fil: Silva, Marcos A. S.. Universidade Federal de Santa Catarina; Brasil
Fil: Cuffini, Silvia Lucia. Universidade Federal Do Sao Paulo; Brasil. Universidade Federal de Santa Catarina; Brasil
Materia
POLYMORPHISM
EFAVIRENZ
SOLID
CHARACTERIZATION
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:11336/185881
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/185881
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution propertiesFandaruff, CiniraRauber, Gabriela S.Araya Sibaja, Andrea MarielaPereira, Rafael N.De Campos, Carlos E. M.Rocha, Helvécio V. A.Monti, Gustavo AlbertoMalaspina, ThacianaSilva, Marcos A. S.Cuffini, Silvia LuciaPOLYMORPHISMEFAVIRENZSOLIDCHARACTERIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Polymorphs, cocrystals, solvates, and hydrates have been reported for efavirenz (EFV), which is part of high activity antiretroviral therapy (HAART), and it is considered to be the best choice in the treatment of adults and children. However, studies about thermodynamic stability and improvement of dissolution properties have been rarely reported for the anhydrous polymorphic forms. Therefore, the aim of this work was to characterize the solid state of anhydrous polymorph I and polymorph II (herein obtained), to study the thermodynamic stability and strategies to improve the dissolution properties. In addition, techniques such as, X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), hot stage microscopy (HSM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), raman spectroscopy (RS), theoretical calculations, and solid-state nuclear magnetic resonance (ss-NMR) were used to complete this work. Thermodynamic studies showed that polymorphs I and II are enantiotropically related with the isoenergetic point between 35 and 40 °C. The EFV polymorph II showed itself to be more stable and 10-fold more soluble than polymorph I, due to modifications of morphology. Therefore, polymorph II could be an excellent candidate with significant advantages for pharmaceutical formulations.Fil: Fandaruff, Cinira. Universidade Federal de Santa Catarina; BrasilFil: Rauber, Gabriela S.. Universidade Federal de Santa Catarina; BrasilFil: Araya Sibaja, Andrea Mariela. Universidad de Costa Rica; Costa RicaFil: Pereira, Rafael N.. Universidade Federal de Santa Catarina; BrasilFil: De Campos, Carlos E. M.. Universidade Federal de Santa Catarina; BrasilFil: Rocha, Helvécio V. A.. Fundación Oswaldo Cruz; BrasilFil: Monti, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; ArgentinaFil: Malaspina, Thaciana. Universidade de Sao Paulo; BrasilFil: Silva, Marcos A. S.. Universidade Federal de Santa Catarina; BrasilFil: Cuffini, Silvia Lucia. Universidade Federal Do Sao Paulo; Brasil. Universidade Federal de Santa Catarina; BrasilAmerican Chemical Society2014-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/185881Fandaruff, Cinira; Rauber, Gabriela S.; Araya Sibaja, Andrea Mariela; Pereira, Rafael N.; De Campos, Carlos E. M.; et al.; Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties; American Chemical Society; Crystal Growth & Design; 14; 10; 10-2014; 4968-49751528-74831528-7505CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/cg500509cinfo:eu-repo/semantics/altIdentifier/doi/10.1021/cg500509cinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:45:17Zoai:ri.conicet.gov.ar:11336/185881instacron: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 10:45:17.448CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
title Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
spellingShingle Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
Fandaruff, Cinira
POLYMORPHISM
EFAVIRENZ
SOLID
CHARACTERIZATION
title_short Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
title_full Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
title_fullStr Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
title_full_unstemmed Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
title_sort Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties
dc.creator.none.fl_str_mv Fandaruff, Cinira
Rauber, Gabriela S.
Araya Sibaja, Andrea Mariela
Pereira, Rafael N.
De Campos, Carlos E. M.
Rocha, Helvécio V. A.
Monti, Gustavo Alberto
Malaspina, Thaciana
Silva, Marcos A. S.
Cuffini, Silvia Lucia
author Fandaruff, Cinira
author_facet Fandaruff, Cinira
Rauber, Gabriela S.
Araya Sibaja, Andrea Mariela
Pereira, Rafael N.
De Campos, Carlos E. M.
Rocha, Helvécio V. A.
Monti, Gustavo Alberto
Malaspina, Thaciana
Silva, Marcos A. S.
Cuffini, Silvia Lucia
author_role author
author2 Rauber, Gabriela S.
Araya Sibaja, Andrea Mariela
Pereira, Rafael N.
De Campos, Carlos E. M.
Rocha, Helvécio V. A.
Monti, Gustavo Alberto
Malaspina, Thaciana
Silva, Marcos A. S.
Cuffini, Silvia Lucia
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv POLYMORPHISM
EFAVIRENZ
SOLID
CHARACTERIZATION
topic POLYMORPHISM
EFAVIRENZ
SOLID
CHARACTERIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Polymorphs, cocrystals, solvates, and hydrates have been reported for efavirenz (EFV), which is part of high activity antiretroviral therapy (HAART), and it is considered to be the best choice in the treatment of adults and children. However, studies about thermodynamic stability and improvement of dissolution properties have been rarely reported for the anhydrous polymorphic forms. Therefore, the aim of this work was to characterize the solid state of anhydrous polymorph I and polymorph II (herein obtained), to study the thermodynamic stability and strategies to improve the dissolution properties. In addition, techniques such as, X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), hot stage microscopy (HSM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), raman spectroscopy (RS), theoretical calculations, and solid-state nuclear magnetic resonance (ss-NMR) were used to complete this work. Thermodynamic studies showed that polymorphs I and II are enantiotropically related with the isoenergetic point between 35 and 40 °C. The EFV polymorph II showed itself to be more stable and 10-fold more soluble than polymorph I, due to modifications of morphology. Therefore, polymorph II could be an excellent candidate with significant advantages for pharmaceutical formulations.
Fil: Fandaruff, Cinira. Universidade Federal de Santa Catarina; Brasil
Fil: Rauber, Gabriela S.. Universidade Federal de Santa Catarina; Brasil
Fil: Araya Sibaja, Andrea Mariela. Universidad de Costa Rica; Costa Rica
Fil: Pereira, Rafael N.. Universidade Federal de Santa Catarina; Brasil
Fil: De Campos, Carlos E. M.. Universidade Federal de Santa Catarina; Brasil
Fil: Rocha, Helvécio V. A.. Fundación Oswaldo Cruz; Brasil
Fil: Monti, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; Argentina
Fil: Malaspina, Thaciana. Universidade de Sao Paulo; Brasil
Fil: Silva, Marcos A. S.. Universidade Federal de Santa Catarina; Brasil
Fil: Cuffini, Silvia Lucia. Universidade Federal Do Sao Paulo; Brasil. Universidade Federal de Santa Catarina; Brasil
description Polymorphs, cocrystals, solvates, and hydrates have been reported for efavirenz (EFV), which is part of high activity antiretroviral therapy (HAART), and it is considered to be the best choice in the treatment of adults and children. However, studies about thermodynamic stability and improvement of dissolution properties have been rarely reported for the anhydrous polymorphic forms. Therefore, the aim of this work was to characterize the solid state of anhydrous polymorph I and polymorph II (herein obtained), to study the thermodynamic stability and strategies to improve the dissolution properties. In addition, techniques such as, X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), hot stage microscopy (HSM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), raman spectroscopy (RS), theoretical calculations, and solid-state nuclear magnetic resonance (ss-NMR) were used to complete this work. Thermodynamic studies showed that polymorphs I and II are enantiotropically related with the isoenergetic point between 35 and 40 °C. The EFV polymorph II showed itself to be more stable and 10-fold more soluble than polymorph I, due to modifications of morphology. Therefore, polymorph II could be an excellent candidate with significant advantages for pharmaceutical formulations.
publishDate 2014
dc.date.none.fl_str_mv 2014-10
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/11336/185881
Fandaruff, Cinira; Rauber, Gabriela S.; Araya Sibaja, Andrea Mariela; Pereira, Rafael N.; De Campos, Carlos E. M.; et al.; Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties; American Chemical Society; Crystal Growth & Design; 14; 10; 10-2014; 4968-4975
1528-7483
1528-7505
CONICET Digital
CONICET
url http://hdl.handle.net/11336/185881
identifier_str_mv Fandaruff, Cinira; Rauber, Gabriela S.; Araya Sibaja, Andrea Mariela; Pereira, Rafael N.; De Campos, Carlos E. M.; et al.; Polymorphism of anti-HIV drug efavirenz: Investigations on thermodynamic and dissolution properties; American Chemical Society; Crystal Growth & Design; 14; 10; 10-2014; 4968-4975
1528-7483
1528-7505
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://pubs.acs.org/doi/10.1021/cg500509c
info:eu-repo/semantics/altIdentifier/doi/10.1021/cg500509c
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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