Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate

Autores
Salazar Rojas, Duvernis Maria; Maggio, Ruben Mariano; Kaufman, Teodoro Saul
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Praziquantel (PZQ) is a highly effective low-cost anthelmintic agent used as the first-choice treatment against schistosomiasis. The low solubility of the active is a major drawback for pharmaceutical formulation. A valid approach of the pharmaceutical industry for the improvement of the pharmacotechnical features of the active principles (such as solubility, processability, stability, among others), is the preparation of new solid forms, such as salts, polymorph, and pseudo-polymorph. Herein we report the preparation and characterization of a new solid form PZQ. The PZQ monohydrate (PZQ-MH) was prepared by a solventless procedure from the commercial racemate and the product was characterized at the solid-state employing optical digital microscopy, thermal methods (melting point, differential scanning calorimetry and thermogravimetric analysis), as well as and mid-infrared and near infrared spectroscopies. The chemical structure and content of water were full assessed by 1H nuclear magnetic resonance (NMR) in solution. The amount of water in PZQ-was also determined by different approaches, including thermogravimetric analysis and the loss on drying test. Solid-state 13C NMR (ssNMR) and X-ray powder diffraction (XRPD) completed the structural characterization of the new monohydrate. PZQ-MH showed a crystalline behavior during XRPD experiments and showed relevant differences in spectroscopic, calorimetric, ssNMR and XRPD signals when it was compared with the known crystal (Form A) and amorphous forms of PZQ. The determination of the intrinsic dissolution rate (IDR) of PZQ-MH was carried out as a functional characterization, observing that the new form had slightly higher IDR than Form A.
Fil: Salazar Rojas, Duvernis Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Maggio, Ruben Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Materia
DSC AND TGA
MONOHYDRATE
PSEUDO-POLYMORPHISM
RACEMIC PRAZIQUANTEL
SOLID-STATE CHARACTERIZATION
VIBRATIONAL SPECTROSCOPY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/127163
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/127163
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrateSalazar Rojas, Duvernis MariaMaggio, Ruben MarianoKaufman, Teodoro SaulDSC AND TGAMONOHYDRATEPSEUDO-POLYMORPHISMRACEMIC PRAZIQUANTELSOLID-STATE CHARACTERIZATIONVIBRATIONAL SPECTROSCOPYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Praziquantel (PZQ) is a highly effective low-cost anthelmintic agent used as the first-choice treatment against schistosomiasis. The low solubility of the active is a major drawback for pharmaceutical formulation. A valid approach of the pharmaceutical industry for the improvement of the pharmacotechnical features of the active principles (such as solubility, processability, stability, among others), is the preparation of new solid forms, such as salts, polymorph, and pseudo-polymorph. Herein we report the preparation and characterization of a new solid form PZQ. The PZQ monohydrate (PZQ-MH) was prepared by a solventless procedure from the commercial racemate and the product was characterized at the solid-state employing optical digital microscopy, thermal methods (melting point, differential scanning calorimetry and thermogravimetric analysis), as well as and mid-infrared and near infrared spectroscopies. The chemical structure and content of water were full assessed by 1H nuclear magnetic resonance (NMR) in solution. The amount of water in PZQ-was also determined by different approaches, including thermogravimetric analysis and the loss on drying test. Solid-state 13C NMR (ssNMR) and X-ray powder diffraction (XRPD) completed the structural characterization of the new monohydrate. PZQ-MH showed a crystalline behavior during XRPD experiments and showed relevant differences in spectroscopic, calorimetric, ssNMR and XRPD signals when it was compared with the known crystal (Form A) and amorphous forms of PZQ. The determination of the intrinsic dissolution rate (IDR) of PZQ-MH was carried out as a functional characterization, observing that the new form had slightly higher IDR than Form A.Fil: Salazar Rojas, Duvernis Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; ArgentinaFil: Maggio, Ruben Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; ArgentinaElsevier Science2020-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/127163Salazar Rojas, Duvernis Maria; Maggio, Ruben Mariano; Kaufman, Teodoro Saul; Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate; Elsevier Science; European Journal of Pharmaceutical Sciences; 146; 4-2020; 1-90928-0987CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejps.2020.105267info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0928098720300567info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:06:02Zoai:ri.conicet.gov.ar:11336/127163instacron: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 10:06:02.504CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
title Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
spellingShingle Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
Salazar Rojas, Duvernis Maria
DSC AND TGA
MONOHYDRATE
PSEUDO-POLYMORPHISM
RACEMIC PRAZIQUANTEL
SOLID-STATE CHARACTERIZATION
VIBRATIONAL SPECTROSCOPY
title_short Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
title_full Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
title_fullStr Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
title_full_unstemmed Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
title_sort Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate
dc.creator.none.fl_str_mv Salazar Rojas, Duvernis Maria
Maggio, Ruben Mariano
Kaufman, Teodoro Saul
author Salazar Rojas, Duvernis Maria
author_facet Salazar Rojas, Duvernis Maria
Maggio, Ruben Mariano
Kaufman, Teodoro Saul
author_role author
author2 Maggio, Ruben Mariano
Kaufman, Teodoro Saul
author2_role author
author
dc.subject.none.fl_str_mv DSC AND TGA
MONOHYDRATE
PSEUDO-POLYMORPHISM
RACEMIC PRAZIQUANTEL
SOLID-STATE CHARACTERIZATION
VIBRATIONAL SPECTROSCOPY
topic DSC AND TGA
MONOHYDRATE
PSEUDO-POLYMORPHISM
RACEMIC PRAZIQUANTEL
SOLID-STATE CHARACTERIZATION
VIBRATIONAL 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 Praziquantel (PZQ) is a highly effective low-cost anthelmintic agent used as the first-choice treatment against schistosomiasis. The low solubility of the active is a major drawback for pharmaceutical formulation. A valid approach of the pharmaceutical industry for the improvement of the pharmacotechnical features of the active principles (such as solubility, processability, stability, among others), is the preparation of new solid forms, such as salts, polymorph, and pseudo-polymorph. Herein we report the preparation and characterization of a new solid form PZQ. The PZQ monohydrate (PZQ-MH) was prepared by a solventless procedure from the commercial racemate and the product was characterized at the solid-state employing optical digital microscopy, thermal methods (melting point, differential scanning calorimetry and thermogravimetric analysis), as well as and mid-infrared and near infrared spectroscopies. The chemical structure and content of water were full assessed by 1H nuclear magnetic resonance (NMR) in solution. The amount of water in PZQ-was also determined by different approaches, including thermogravimetric analysis and the loss on drying test. Solid-state 13C NMR (ssNMR) and X-ray powder diffraction (XRPD) completed the structural characterization of the new monohydrate. PZQ-MH showed a crystalline behavior during XRPD experiments and showed relevant differences in spectroscopic, calorimetric, ssNMR and XRPD signals when it was compared with the known crystal (Form A) and amorphous forms of PZQ. The determination of the intrinsic dissolution rate (IDR) of PZQ-MH was carried out as a functional characterization, observing that the new form had slightly higher IDR than Form A.
Fil: Salazar Rojas, Duvernis Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Maggio, Ruben Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina
description Praziquantel (PZQ) is a highly effective low-cost anthelmintic agent used as the first-choice treatment against schistosomiasis. The low solubility of the active is a major drawback for pharmaceutical formulation. A valid approach of the pharmaceutical industry for the improvement of the pharmacotechnical features of the active principles (such as solubility, processability, stability, among others), is the preparation of new solid forms, such as salts, polymorph, and pseudo-polymorph. Herein we report the preparation and characterization of a new solid form PZQ. The PZQ monohydrate (PZQ-MH) was prepared by a solventless procedure from the commercial racemate and the product was characterized at the solid-state employing optical digital microscopy, thermal methods (melting point, differential scanning calorimetry and thermogravimetric analysis), as well as and mid-infrared and near infrared spectroscopies. The chemical structure and content of water were full assessed by 1H nuclear magnetic resonance (NMR) in solution. The amount of water in PZQ-was also determined by different approaches, including thermogravimetric analysis and the loss on drying test. Solid-state 13C NMR (ssNMR) and X-ray powder diffraction (XRPD) completed the structural characterization of the new monohydrate. PZQ-MH showed a crystalline behavior during XRPD experiments and showed relevant differences in spectroscopic, calorimetric, ssNMR and XRPD signals when it was compared with the known crystal (Form A) and amorphous forms of PZQ. The determination of the intrinsic dissolution rate (IDR) of PZQ-MH was carried out as a functional characterization, observing that the new form had slightly higher IDR than Form A.
publishDate 2020
dc.date.none.fl_str_mv 2020-04
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/11336/127163
Salazar Rojas, Duvernis Maria; Maggio, Ruben Mariano; Kaufman, Teodoro Saul; Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate; Elsevier Science; European Journal of Pharmaceutical Sciences; 146; 4-2020; 1-9
0928-0987
CONICET Digital
CONICET
url http://hdl.handle.net/11336/127163
identifier_str_mv Salazar Rojas, Duvernis Maria; Maggio, Ruben Mariano; Kaufman, Teodoro Saul; Preparation and characterization of a new solid form of praziquantel, an essential anthelmintic drug: Praziquantel racemic monohydrate; Elsevier Science; European Journal of Pharmaceutical Sciences; 146; 4-2020; 1-9
0928-0987
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejps.2020.105267
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0928098720300567
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 13.13397

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