Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics
Oxidation is a prominent degradation route of biological molecules that produces a wide variety of degradation products through complex mechanisms and hence qualifies to be a vital pharmaceutical process. This article presents the kinetic and spectral study of the oxidation of an antimigraine drug r...
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| Format: | Article |
| Language: | English |
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De Gruyter
2023-05-01
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| Series: | Open Chemistry |
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| Online Access: | https://doi.org/10.1515/chem-2022-0341 |
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| author | Malini S. Raj Kalyan Kumari Latha Jayant Lakshmi Shettihalli Ashok Kumar Appaji Abhishek |
| author_facet | Malini S. Raj Kalyan Kumari Latha Jayant Lakshmi Shettihalli Ashok Kumar Appaji Abhishek |
| author_sort | Malini S. |
| collection | DOAJ |
| description | Oxidation is a prominent degradation route of biological molecules that produces a wide variety of degradation products through complex mechanisms and hence qualifies to be a vital pharmaceutical process. This article presents the kinetic and spectral study of the oxidation of an antimigraine drug rizatriptan benzoate (RTB) in an acid medium with the aid of a mild biocidal oxidant N-chloro-p-toluenesulfonamide, referred to as chloramine-T (CAT). The kinetic experimental studies reported here, such as fractional order dependency on RTB, pseudo-first-order dependency on CAT, negative fractional order dependency on the acid medium, independent of the rate on the ionic concentration and increasing rate with increasing dielectric constant, have led to the evaluation of stoichiometry, thermodynamic properties, and derivation of a rate equation. Effective interpretation of UV–Vis, IR, 1H and 13C NMR investigation was performed to identify and confirm the identity of the oxidation products and discuss the involved plausible mechanism. This study provides an extended insight into the products of oxidation formed during the metabolism of RTB. |
| first_indexed | 2024-03-13T07:14:43Z |
| format | Article |
| id | doaj.art-1ca1e03cc815477abe3184d0f75f1371 |
| institution | Directory Open Access Journal |
| issn | 2391-5420 |
| language | English |
| last_indexed | 2024-03-13T07:14:43Z |
| publishDate | 2023-05-01 |
| publisher | De Gruyter |
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| series | Open Chemistry |
| spelling | doaj.art-1ca1e03cc815477abe3184d0f75f13712023-06-05T09:16:57ZengDe GruyterOpen Chemistry2391-54202023-05-012111710.1515/chem-2022-0341Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kineticsMalini S.0Raj Kalyan1Kumari Latha2Jayant Lakshmi3Shettihalli Ashok Kumar4Appaji Abhishek5Department of Chemistry, B.M.S. College of Engineering, Bengaluru, IndiaDepartment of Chemistry, B.M.S. College of Engineering, Bengaluru, IndiaDepartment of Physics and Centre for Nano-Materials and Displays, B.M.S. College of Engineering, Bengaluru, IndiaDepartment of Chemical Engineering, Dayananda Sagar College of Engineering, Bengaluru, IndiaDepartment of Biotechnology, B.M.S. College of Engineering, Bengaluru, 560019, IndiaDepartment of Medical Electronics Engineering, B.M.S. College of Engineering, Bengaluru, IndiaOxidation is a prominent degradation route of biological molecules that produces a wide variety of degradation products through complex mechanisms and hence qualifies to be a vital pharmaceutical process. This article presents the kinetic and spectral study of the oxidation of an antimigraine drug rizatriptan benzoate (RTB) in an acid medium with the aid of a mild biocidal oxidant N-chloro-p-toluenesulfonamide, referred to as chloramine-T (CAT). The kinetic experimental studies reported here, such as fractional order dependency on RTB, pseudo-first-order dependency on CAT, negative fractional order dependency on the acid medium, independent of the rate on the ionic concentration and increasing rate with increasing dielectric constant, have led to the evaluation of stoichiometry, thermodynamic properties, and derivation of a rate equation. Effective interpretation of UV–Vis, IR, 1H and 13C NMR investigation was performed to identify and confirm the identity of the oxidation products and discuss the involved plausible mechanism. This study provides an extended insight into the products of oxidation formed during the metabolism of RTB.https://doi.org/10.1515/chem-2022-0341rizatriptan benzoateoxidation productkineticschloramine tspectrophotometric analysis1h and 13c nuclear magnetic resonanceindoleimide |
| spellingShingle | Malini S. Raj Kalyan Kumari Latha Jayant Lakshmi Shettihalli Ashok Kumar Appaji Abhishek Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics Open Chemistry rizatriptan benzoate oxidation product kinetics chloramine t spectrophotometric analysis 1h and 13c nuclear magnetic resonance indole imide |
| title | Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics |
| title_full | Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics |
| title_fullStr | Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics |
| title_full_unstemmed | Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics |
| title_short | Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics |
| title_sort | chloramine t induced oxidation of rizatriptan benzoate an integral chemical and spectroscopic study of products mechanisms and kinetics |
| topic | rizatriptan benzoate oxidation product kinetics chloramine t spectrophotometric analysis 1h and 13c nuclear magnetic resonance indole imide |
| url | https://doi.org/10.1515/chem-2022-0341 |
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