Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition

Autores
Bianchini, Romina Marcela; Castellano, Patricia Margarita; Kaufman, Teodoro Saul
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A photostability study of Valsartan (VAL) is reported. Exposure of the drug to UV-vis radiation (λ> 320 nm) yielded two previously unknown compounds, which were detected by HPLC. Preparative amounts of the new potential degradation products (DP-1 and DP-2) were obtained by submitting VAL bulk drug to extensive photodegradation. The impurities were isolated by preparative normal phase column chromatography. Analytical information from the infrared, nuclear magnetic resonance and mass spectral data of the degradation products revealed their structures as N-[2′-(1. H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N-isobutylpentanamide (DP-1) and N-(diazirino[1,3-f]phenanthridin-4-ylmethyl)-N-isobutylpentanamide (DP-2). DP-1 arose from decarboxylation of VAL, while DP-2 results from further loss of nitrogen from the tetrazole motif of DP-1, with concomitant cyclization to yield a tetracyclic diazacyclopropene derivative.
Fil: Bianchini, Romina Marcela. 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
Fil: Castellano, Patricia Margarita. 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
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
Materia
NMR SPECTROSCOPIC ANALYSIS
PHOTODEGRADATION
POTENTIAL IMPURITIES
STRUCTURAL ELUCIDATION
VALSARTAN
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:11336/127160
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/127160
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Characterization of two new potential impurities of Valsartan obtained under photodegradation stress conditionBianchini, Romina MarcelaCastellano, Patricia MargaritaKaufman, Teodoro SaulNMR SPECTROSCOPIC ANALYSISPHOTODEGRADATIONPOTENTIAL IMPURITIESSTRUCTURAL ELUCIDATIONVALSARTANhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A photostability study of Valsartan (VAL) is reported. Exposure of the drug to UV-vis radiation (λ> 320 nm) yielded two previously unknown compounds, which were detected by HPLC. Preparative amounts of the new potential degradation products (DP-1 and DP-2) were obtained by submitting VAL bulk drug to extensive photodegradation. The impurities were isolated by preparative normal phase column chromatography. Analytical information from the infrared, nuclear magnetic resonance and mass spectral data of the degradation products revealed their structures as N-[2′-(1. H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N-isobutylpentanamide (DP-1) and N-(diazirino[1,3-f]phenanthridin-4-ylmethyl)-N-isobutylpentanamide (DP-2). DP-1 arose from decarboxylation of VAL, while DP-2 results from further loss of nitrogen from the tetrazole motif of DP-1, with concomitant cyclization to yield a tetracyclic diazacyclopropene derivative.Fil: Bianchini, Romina Marcela. 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; ArgentinaFil: Castellano, Patricia Margarita. 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; 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; ArgentinaElsevier Science2011-08-25info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/127160Bianchini, Romina Marcela; Castellano, Patricia Margarita; Kaufman, Teodoro Saul; Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 56; 1; 25-8-2011; 16-220731-7085CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0731708511002287info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jpba.2011.04.017info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:59:12Zoai:ri.conicet.gov.ar:11336/127160instacron: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 09:59:13.03CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
title Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
spellingShingle Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
Bianchini, Romina Marcela
NMR SPECTROSCOPIC ANALYSIS
PHOTODEGRADATION
POTENTIAL IMPURITIES
STRUCTURAL ELUCIDATION
VALSARTAN
title_short Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
title_full Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
title_fullStr Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
title_full_unstemmed Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
title_sort Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition
dc.creator.none.fl_str_mv Bianchini, Romina Marcela
Castellano, Patricia Margarita
Kaufman, Teodoro Saul
author Bianchini, Romina Marcela
author_facet Bianchini, Romina Marcela
Castellano, Patricia Margarita
Kaufman, Teodoro Saul
author_role author
author2 Castellano, Patricia Margarita
Kaufman, Teodoro Saul
author2_role author
author
dc.subject.none.fl_str_mv NMR SPECTROSCOPIC ANALYSIS
PHOTODEGRADATION
POTENTIAL IMPURITIES
STRUCTURAL ELUCIDATION
VALSARTAN
topic NMR SPECTROSCOPIC ANALYSIS
PHOTODEGRADATION
POTENTIAL IMPURITIES
STRUCTURAL ELUCIDATION
VALSARTAN
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A photostability study of Valsartan (VAL) is reported. Exposure of the drug to UV-vis radiation (λ> 320 nm) yielded two previously unknown compounds, which were detected by HPLC. Preparative amounts of the new potential degradation products (DP-1 and DP-2) were obtained by submitting VAL bulk drug to extensive photodegradation. The impurities were isolated by preparative normal phase column chromatography. Analytical information from the infrared, nuclear magnetic resonance and mass spectral data of the degradation products revealed their structures as N-[2′-(1. H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N-isobutylpentanamide (DP-1) and N-(diazirino[1,3-f]phenanthridin-4-ylmethyl)-N-isobutylpentanamide (DP-2). DP-1 arose from decarboxylation of VAL, while DP-2 results from further loss of nitrogen from the tetrazole motif of DP-1, with concomitant cyclization to yield a tetracyclic diazacyclopropene derivative.
Fil: Bianchini, Romina Marcela. 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
Fil: Castellano, Patricia Margarita. 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
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
description A photostability study of Valsartan (VAL) is reported. Exposure of the drug to UV-vis radiation (λ> 320 nm) yielded two previously unknown compounds, which were detected by HPLC. Preparative amounts of the new potential degradation products (DP-1 and DP-2) were obtained by submitting VAL bulk drug to extensive photodegradation. The impurities were isolated by preparative normal phase column chromatography. Analytical information from the infrared, nuclear magnetic resonance and mass spectral data of the degradation products revealed their structures as N-[2′-(1. H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N-isobutylpentanamide (DP-1) and N-(diazirino[1,3-f]phenanthridin-4-ylmethyl)-N-isobutylpentanamide (DP-2). DP-1 arose from decarboxylation of VAL, while DP-2 results from further loss of nitrogen from the tetrazole motif of DP-1, with concomitant cyclization to yield a tetracyclic diazacyclopropene derivative.
publishDate 2011
dc.date.none.fl_str_mv 2011-08-25
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/11336/127160
Bianchini, Romina Marcela; Castellano, Patricia Margarita; Kaufman, Teodoro Saul; Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 56; 1; 25-8-2011; 16-22
0731-7085
CONICET Digital
CONICET
url http://hdl.handle.net/11336/127160
identifier_str_mv Bianchini, Romina Marcela; Castellano, Patricia Margarita; Kaufman, Teodoro Saul; Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 56; 1; 25-8-2011; 16-22
0731-7085
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://www.sciencedirect.com/science/article/abs/pii/S0731708511002287
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jpba.2011.04.017
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 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 13.070432

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