Esterification of Metronidazole and its Complexation with β -Cyclodextrin: A Strategy for Enhanced Aqueous Solubility
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2025
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| _version_ | 1866901574959235072 |
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| author | Rahul Patil*1, Sandip Patil2, Gaurav Gupta2, Harpalsing Girase3 |
| author_facet | Rahul Patil*1, Sandip Patil2, Gaurav Gupta2, Harpalsing Girase3 |
| contents | <p><span lang="EN-IN">A common antibacterial drug, metronidazole has drawbacks such as poor water solubility, a harsh taste, and decreased absorption. Inclusion complexes of ester derivatives of Metronidazole with β-cyclodextrin were created and characterized in order to get around these problems. The transformation of metronidazole into its ester derivatives has been carried out in this work. Using pyridine as a catalyst, metronidazole was esterified with acetyl and benzoyl chlorides in DCM to yield metronidazole acetate and metronidazole benzoate. To verify their structure and purity, synthesized ester derivatives were characterized using 1H-NMR, 13C-NMR, and FT-IR. Ester derivatives were molecularly incorporated into β-cyclodextrin via solvent evaporation method to further enhance aqueous solubility. 1H-NMR, 13C-NMR, and FT-IR spectroscopy methods were used to confirm these inclusion complexes. The water solubility of the synthesised metronidazole ester derivatives and their inclusion complexes with β-cyclodextrin was assessed using the shake flask method. After encapsulation of esters within the β-cyclodextrin cavity, a notable improvement in solubility was observed, demonstrating the efficacy of molecular inclusion in boosting the water solubility of the less soluble ester derivatives. The study shows that prodrug derivatization in conjunction with β-Cyclodextrin encapsulation is a potential approach to creating new inclusion complexes. This approach provides a viable way to use molecular encapsulation techniques to enhance metronidazole's pharmacological performance</span><span>.</span></p> |
| format | Recurso digital |
| id | zenodo_https___doi_org_10_5281_zenodo_16669416 |
| institution | Zenodo |
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| publishDate | 2025 |
| publisher | Zenodo |
| record_format | zenodo |
| spellingShingle | Esterification of Metronidazole and its Complexation with β -Cyclodextrin: A Strategy for Enhanced Aqueous Solubility Rahul Patil*1, Sandip Patil2, Gaurav Gupta2, Harpalsing Girase3 Inclusion complex, Metronidazole acetate, Metronidazole benzoate, β-cyclodextrin <p><span lang="EN-IN">A common antibacterial drug, metronidazole has drawbacks such as poor water solubility, a harsh taste, and decreased absorption. Inclusion complexes of ester derivatives of Metronidazole with β-cyclodextrin were created and characterized in order to get around these problems. The transformation of metronidazole into its ester derivatives has been carried out in this work. Using pyridine as a catalyst, metronidazole was esterified with acetyl and benzoyl chlorides in DCM to yield metronidazole acetate and metronidazole benzoate. To verify their structure and purity, synthesized ester derivatives were characterized using 1H-NMR, 13C-NMR, and FT-IR. Ester derivatives were molecularly incorporated into β-cyclodextrin via solvent evaporation method to further enhance aqueous solubility. 1H-NMR, 13C-NMR, and FT-IR spectroscopy methods were used to confirm these inclusion complexes. The water solubility of the synthesised metronidazole ester derivatives and their inclusion complexes with β-cyclodextrin was assessed using the shake flask method. After encapsulation of esters within the β-cyclodextrin cavity, a notable improvement in solubility was observed, demonstrating the efficacy of molecular inclusion in boosting the water solubility of the less soluble ester derivatives. The study shows that prodrug derivatization in conjunction with β-Cyclodextrin encapsulation is a potential approach to creating new inclusion complexes. This approach provides a viable way to use molecular encapsulation techniques to enhance metronidazole's pharmacological performance</span><span>.</span></p> |
| title | Esterification of Metronidazole and its Complexation with β -Cyclodextrin: A Strategy for Enhanced Aqueous Solubility |
| topic | Inclusion complex, Metronidazole acetate, Metronidazole benzoate, β-cyclodextrin |
| url | https://doi.org/10.5281/zenodo.16669416 |