Degradation profile of nepafenac in aqueous solution and structural characterization of a novel degradation product.
Benzylic oxidation
Drug stability
HPLC
Nepafenac
α-Ketoacid
Journal
Journal of pharmaceutical and biomedical analysis
ISSN: 1873-264X
Titre abrégé: J Pharm Biomed Anal
Pays: England
ID NLM: 8309336
Informations de publication
Date de publication:
10 Sep 2020
10 Sep 2020
Historique:
received:
06
04
2020
revised:
09
06
2020
accepted:
13
06
2020
pubmed:
28
6
2020
medline:
22
6
2021
entrez:
28
6
2020
Statut:
ppublish
Résumé
The stability of the anti-inflammatory drug nepafenac was investigated in aqueous solutions containing hydroxypropyl-β-cyclodextrin at three different values of pH and degradation products were identified. (2-Amino-3-benzoyl)-oxoacetic acid, previously not reported as nepafenac-related impurity, was isolated and structurally characterized by NMR and ESI-MS analyses. It was also shown that the formation of this α-ketoacid from nepafenac in alkaline water/organic cosolvent solution occurs through an aerobic oxidation of the key intermediate 7-benzoyl-1,3-dihydro-indol-2-one, which in some extent is protected from oxidation in the presence of the cyclodextrin additive.
Identifiants
pubmed: 32592943
pii: S0731-7085(20)31318-2
doi: 10.1016/j.jpba.2020.113432
pii:
doi:
Substances chimiques
Benzeneacetamides
0
Phenylacetates
0
Water
059QF0KO0R
nepafenac
0J9L7J6V8C
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
113432Informations de copyright
Copyright © 2020 Elsevier B.V. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.