Structural elucidation of rabeprazole sodium photodegradation products
Rabeprazole sodium is a proton pump inhibitor, used in acid-related disorders, like peptic ulcers and gastroesophageal reflux. It is known to be an acid-labile drug, however, few data about its stability under other factors are available. The aim of this work was to study the photodegradation of rab...
Guardado en:
| Publicado: |
2008
|
|---|---|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07317085_v46_n1_p88_Garcia http://hdl.handle.net/20.500.12110/paper_07317085_v46_n1_p88_Garcia |
| Aporte de: |
| id |
paper:paper_07317085_v46_n1_p88_Garcia |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_07317085_v46_n1_p88_Garcia2023-06-08T15:43:53Z Structural elucidation of rabeprazole sodium photodegradation products Benzimidazole Kinetics Photodegradation products Photostability Proton pump inhibitor Rabeprazole benzimidazole chloroform halide methanol rabeprazole article chemical reaction drug isolation drug stability drug structure enzyme kinetics high performance liquid chromatography nuclear magnetic resonance photodegradation priority journal tablet ultraviolet C radiation 2-Pyridinylmethylsulfinylbenzimidazoles Benzimidazoles Carbon Isotopes Chromatography, High Pressure Liquid Color Drug Contamination Drug Stability Hydrochloric Acid Hydrogen Peroxide Kinetics Magnetic Resonance Spectroscopy Methanol Molecular Conformation Powders Pyridines Solutions Stereoisomerism Tablets Temperature Time Factors Tritium Ultraviolet Rays Rabeprazole sodium is a proton pump inhibitor, used in acid-related disorders, like peptic ulcers and gastroesophageal reflux. It is known to be an acid-labile drug, however, few data about its stability under other factors are available. The aim of this work was to study the photodegradation of rabeprazole, to determine its kinetics and to elucidate the structures of the main degradation products. UVC-254 nm and metal-halide lamps were used. The analysis of the samples was carried out by HPLC. When the drug was in methanol solution, one main degradation product was formed; the degradation rate followed zero-order kinetics. The 1H and 13C NMR spectroscopic determinations revealed the product was the benzimidazolone. Another isolated product was identified as benzimidazole. The latter was confirmed against an authentic sample. A third photodegradation product was identified as the [4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl]methanol, by 1H and 13C NMR of the reaction mixture in chloroform-d. When powdered commercial tablets were exposed to UVC irradiation, they showed the same degradation products along with other unidentified, which appeared as traces; the degradation rate was slower than in solution. The intact tablets were stable after 50 days of exposition to the same light source. © 2007 Elsevier B.V. All rights reserved. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07317085_v46_n1_p88_Garcia http://hdl.handle.net/20.500.12110/paper_07317085_v46_n1_p88_Garcia |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Benzimidazole Kinetics Photodegradation products Photostability Proton pump inhibitor Rabeprazole benzimidazole chloroform halide methanol rabeprazole article chemical reaction drug isolation drug stability drug structure enzyme kinetics high performance liquid chromatography nuclear magnetic resonance photodegradation priority journal tablet ultraviolet C radiation 2-Pyridinylmethylsulfinylbenzimidazoles Benzimidazoles Carbon Isotopes Chromatography, High Pressure Liquid Color Drug Contamination Drug Stability Hydrochloric Acid Hydrogen Peroxide Kinetics Magnetic Resonance Spectroscopy Methanol Molecular Conformation Powders Pyridines Solutions Stereoisomerism Tablets Temperature Time Factors Tritium Ultraviolet Rays |
| spellingShingle |
Benzimidazole Kinetics Photodegradation products Photostability Proton pump inhibitor Rabeprazole benzimidazole chloroform halide methanol rabeprazole article chemical reaction drug isolation drug stability drug structure enzyme kinetics high performance liquid chromatography nuclear magnetic resonance photodegradation priority journal tablet ultraviolet C radiation 2-Pyridinylmethylsulfinylbenzimidazoles Benzimidazoles Carbon Isotopes Chromatography, High Pressure Liquid Color Drug Contamination Drug Stability Hydrochloric Acid Hydrogen Peroxide Kinetics Magnetic Resonance Spectroscopy Methanol Molecular Conformation Powders Pyridines Solutions Stereoisomerism Tablets Temperature Time Factors Tritium Ultraviolet Rays Structural elucidation of rabeprazole sodium photodegradation products |
| topic_facet |
Benzimidazole Kinetics Photodegradation products Photostability Proton pump inhibitor Rabeprazole benzimidazole chloroform halide methanol rabeprazole article chemical reaction drug isolation drug stability drug structure enzyme kinetics high performance liquid chromatography nuclear magnetic resonance photodegradation priority journal tablet ultraviolet C radiation 2-Pyridinylmethylsulfinylbenzimidazoles Benzimidazoles Carbon Isotopes Chromatography, High Pressure Liquid Color Drug Contamination Drug Stability Hydrochloric Acid Hydrogen Peroxide Kinetics Magnetic Resonance Spectroscopy Methanol Molecular Conformation Powders Pyridines Solutions Stereoisomerism Tablets Temperature Time Factors Tritium Ultraviolet Rays |
| description |
Rabeprazole sodium is a proton pump inhibitor, used in acid-related disorders, like peptic ulcers and gastroesophageal reflux. It is known to be an acid-labile drug, however, few data about its stability under other factors are available. The aim of this work was to study the photodegradation of rabeprazole, to determine its kinetics and to elucidate the structures of the main degradation products. UVC-254 nm and metal-halide lamps were used. The analysis of the samples was carried out by HPLC. When the drug was in methanol solution, one main degradation product was formed; the degradation rate followed zero-order kinetics. The 1H and 13C NMR spectroscopic determinations revealed the product was the benzimidazolone. Another isolated product was identified as benzimidazole. The latter was confirmed against an authentic sample. A third photodegradation product was identified as the [4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl]methanol, by 1H and 13C NMR of the reaction mixture in chloroform-d. When powdered commercial tablets were exposed to UVC irradiation, they showed the same degradation products along with other unidentified, which appeared as traces; the degradation rate was slower than in solution. The intact tablets were stable after 50 days of exposition to the same light source. © 2007 Elsevier B.V. All rights reserved. |
| title |
Structural elucidation of rabeprazole sodium photodegradation products |
| title_short |
Structural elucidation of rabeprazole sodium photodegradation products |
| title_full |
Structural elucidation of rabeprazole sodium photodegradation products |
| title_fullStr |
Structural elucidation of rabeprazole sodium photodegradation products |
| title_full_unstemmed |
Structural elucidation of rabeprazole sodium photodegradation products |
| title_sort |
structural elucidation of rabeprazole sodium photodegradation products |
| publishDate |
2008 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07317085_v46_n1_p88_Garcia http://hdl.handle.net/20.500.12110/paper_07317085_v46_n1_p88_Garcia |
| _version_ |
1768543426866839552 |