Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats

Autores
Castro, Eduardo Fidel; Soraci, Alejandro Luis; Tapia, Maria Ofelia; Fogel, Fernando Adrián
Año de publicación
2000
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The chiral inversion process is a characteristic metabolic pathway for different aryl-2-propionic acids or profens. Important variations have been observed between these individual compounds as well as between animal species. In this study, R(-) fenoprofen [R(-)FPF] and R(-) ketoprofen [R(-) KTF] were used to investigate their comparative stereoconversion in cats. After intravenous (i.v.) administration of R(-) FPF, the percentage of chiral inversion was 93.20±13.70%. A highly significant correlation (r: 0.978) was observed between the clearance of R(-) FPF and the chiral inversion process. After i.v. administration of R(-) KTF, the percentage of inversion was only 36.73±2.8%. No correlation between the clearance of R(-) KTF and this process was observed. R(-) FPF was metabolized by the pathways of thioesterification ? chiral inversion processes. For R(-) KTF, the competitive metabolic pathways, glucuronidation and hydroxylation may be involved. However, these metabolic steps are saturable or less functional in cats. Moreover, the thioesterification of R(-) KTF in in vitro studies has been shown to be important in carnivores. The lack of correlation between clearance and chiral inversion process of R(-) KTF may be finally explained by deviation of thioesterification to other metabolic pathways of lipids and/or aminoacid conjugation, particulary glicine derivatives.
Fil: Castro, Eduardo Fidel. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
Fil: Soraci, Alejandro Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
Fil: Tapia, Maria Ofelia. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fogel, Fernando Adrián. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
Materia
ENANTIOMERS
FENOPROFEN
KETOPROFEN
CAT
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:11336/106490
Acceder
id CONICETDig_f8429581bb5f2ee40c7c8865cbcc72f6
oai_identifier_str oai:ri.conicet.gov.ar:11336/106490
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in catsCastro, Eduardo FidelSoraci, Alejandro LuisTapia, Maria OfeliaFogel, Fernando AdriánENANTIOMERSFENOPROFENKETOPROFENCAThttps://purl.org/becyt/ford/4.3https://purl.org/becyt/ford/4The chiral inversion process is a characteristic metabolic pathway for different aryl-2-propionic acids or profens. Important variations have been observed between these individual compounds as well as between animal species. In this study, R(-) fenoprofen [R(-)FPF] and R(-) ketoprofen [R(-) KTF] were used to investigate their comparative stereoconversion in cats. After intravenous (i.v.) administration of R(-) FPF, the percentage of chiral inversion was 93.20±13.70%. A highly significant correlation (r: 0.978) was observed between the clearance of R(-) FPF and the chiral inversion process. After i.v. administration of R(-) KTF, the percentage of inversion was only 36.73±2.8%. No correlation between the clearance of R(-) KTF and this process was observed. R(-) FPF was metabolized by the pathways of thioesterification ? chiral inversion processes. For R(-) KTF, the competitive metabolic pathways, glucuronidation and hydroxylation may be involved. However, these metabolic steps are saturable or less functional in cats. Moreover, the thioesterification of R(-) KTF in in vitro studies has been shown to be important in carnivores. The lack of correlation between clearance and chiral inversion process of R(-) KTF may be finally explained by deviation of thioesterification to other metabolic pathways of lipids and/or aminoacid conjugation, particulary glicine derivatives.Fil: Castro, Eduardo Fidel. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; ArgentinaFil: Soraci, Alejandro Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; ArgentinaFil: Tapia, Maria Ofelia. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Fogel, Fernando Adrián. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; ArgentinaWiley Blackwell Publishing, Inc2000-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/106490Castro, Eduardo Fidel; Soraci, Alejandro Luis; Tapia, Maria Ofelia; Fogel, Fernando Adrián; Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats; Wiley Blackwell Publishing, Inc; Journal of Veterinary Pharmacology and Therapeutics; 23; 5; 10-2000; 265-2710140-77831365-2885CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1046/j.1365-2885.2000.00280.xinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1046/j.1365-2885.2000.00280.xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:08:32Zoai:ri.conicet.gov.ar:11336/106490instacron: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:34982025-09-10 13:08:32.871CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
title Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
spellingShingle Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
Castro, Eduardo Fidel
ENANTIOMERS
FENOPROFEN
KETOPROFEN
CAT
title_short Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
title_full Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
title_fullStr Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
title_full_unstemmed Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
title_sort Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats
dc.creator.none.fl_str_mv Castro, Eduardo Fidel
Soraci, Alejandro Luis
Tapia, Maria Ofelia
Fogel, Fernando Adrián
author Castro, Eduardo Fidel
author_facet Castro, Eduardo Fidel
Soraci, Alejandro Luis
Tapia, Maria Ofelia
Fogel, Fernando Adrián
author_role author
author2 Soraci, Alejandro Luis
Tapia, Maria Ofelia
Fogel, Fernando Adrián
author2_role author
author
author
dc.subject.none.fl_str_mv ENANTIOMERS
FENOPROFEN
KETOPROFEN
CAT
topic ENANTIOMERS
FENOPROFEN
KETOPROFEN
CAT
purl_subject.fl_str_mv https://purl.org/becyt/ford/4.3
https://purl.org/becyt/ford/4
dc.description.none.fl_txt_mv The chiral inversion process is a characteristic metabolic pathway for different aryl-2-propionic acids or profens. Important variations have been observed between these individual compounds as well as between animal species. In this study, R(-) fenoprofen [R(-)FPF] and R(-) ketoprofen [R(-) KTF] were used to investigate their comparative stereoconversion in cats. After intravenous (i.v.) administration of R(-) FPF, the percentage of chiral inversion was 93.20±13.70%. A highly significant correlation (r: 0.978) was observed between the clearance of R(-) FPF and the chiral inversion process. After i.v. administration of R(-) KTF, the percentage of inversion was only 36.73±2.8%. No correlation between the clearance of R(-) KTF and this process was observed. R(-) FPF was metabolized by the pathways of thioesterification ? chiral inversion processes. For R(-) KTF, the competitive metabolic pathways, glucuronidation and hydroxylation may be involved. However, these metabolic steps are saturable or less functional in cats. Moreover, the thioesterification of R(-) KTF in in vitro studies has been shown to be important in carnivores. The lack of correlation between clearance and chiral inversion process of R(-) KTF may be finally explained by deviation of thioesterification to other metabolic pathways of lipids and/or aminoacid conjugation, particulary glicine derivatives.
Fil: Castro, Eduardo Fidel. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
Fil: Soraci, Alejandro Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
Fil: Tapia, Maria Ofelia. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fogel, Fernando Adrián. Universidad Nacional del Centro de la Provincia de Buenos Aires. Facultad de Ciencia Veterinarias. Departamento de Fisiopatología. Laboratorio de Toxicología; Argentina
description The chiral inversion process is a characteristic metabolic pathway for different aryl-2-propionic acids or profens. Important variations have been observed between these individual compounds as well as between animal species. In this study, R(-) fenoprofen [R(-)FPF] and R(-) ketoprofen [R(-) KTF] were used to investigate their comparative stereoconversion in cats. After intravenous (i.v.) administration of R(-) FPF, the percentage of chiral inversion was 93.20±13.70%. A highly significant correlation (r: 0.978) was observed between the clearance of R(-) FPF and the chiral inversion process. After i.v. administration of R(-) KTF, the percentage of inversion was only 36.73±2.8%. No correlation between the clearance of R(-) KTF and this process was observed. R(-) FPF was metabolized by the pathways of thioesterification ? chiral inversion processes. For R(-) KTF, the competitive metabolic pathways, glucuronidation and hydroxylation may be involved. However, these metabolic steps are saturable or less functional in cats. Moreover, the thioesterification of R(-) KTF in in vitro studies has been shown to be important in carnivores. The lack of correlation between clearance and chiral inversion process of R(-) KTF may be finally explained by deviation of thioesterification to other metabolic pathways of lipids and/or aminoacid conjugation, particulary glicine derivatives.
publishDate 2000
dc.date.none.fl_str_mv 2000-10
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/11336/106490
Castro, Eduardo Fidel; Soraci, Alejandro Luis; Tapia, Maria Ofelia; Fogel, Fernando Adrián; Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats; Wiley Blackwell Publishing, Inc; Journal of Veterinary Pharmacology and Therapeutics; 23; 5; 10-2000; 265-271
0140-7783
1365-2885
CONICET Digital
CONICET
url http://hdl.handle.net/11336/106490
identifier_str_mv Castro, Eduardo Fidel; Soraci, Alejandro Luis; Tapia, Maria Ofelia; Fogel, Fernando Adrián; Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats; Wiley Blackwell Publishing, Inc; Journal of Veterinary Pharmacology and Therapeutics; 23; 5; 10-2000; 265-271
0140-7783
1365-2885
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1046/j.1365-2885.2000.00280.x
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1046/j.1365-2885.2000.00280.x
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
application/pdf
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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
_version_ 1842980406322790400
score 12.993085

Publicaciones similares