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Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole

A one-pot method for the preparation of benzoyl metronidazole was achieved by using N,N′-carbonyldiimidazole as a coupling reagent. Moreover, it was found that the byproduct imidazole as the catalyst promoted the reaction. In addition, the β-cyclodextrin solubilization of benzoyl metronidazole was i...

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Detalles Bibliográficos
Autores principales: Huang, Qing, Li, Benpeng, Yang, Shuo, Ma, Peipei, Wang, Zhizhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi Publishing Corporation 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3732634/
https://www.ncbi.nlm.nih.gov/pubmed/23970831
http://dx.doi.org/10.1155/2013/306476
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author Huang, Qing
Li, Benpeng
Yang, Shuo
Ma, Peipei
Wang, Zhizhong
author_facet Huang, Qing
Li, Benpeng
Yang, Shuo
Ma, Peipei
Wang, Zhizhong
author_sort Huang, Qing
collection PubMed
description A one-pot method for the preparation of benzoyl metronidazole was achieved by using N,N′-carbonyldiimidazole as a coupling reagent. Moreover, it was found that the byproduct imidazole as the catalyst promoted the reaction. In addition, the β-cyclodextrin solubilization of benzoyl metronidazole was investigated by phase-solubility method. The phase-solubility studies indicated that the solubility of benzoyl metronidazole (S = 0.1435 g/L) was substantially increased 9.7-fold (S′ = 1.3881 g/L) by formation of 1 : 1 benzoyl metronidazole/β-cyclodextrin complexes in water, and the association constant K (a) value was determined to be 251 (±23) dm(3)/mol. Therefore, β-cyclodextrin can work as a pharmaceutical solubilizer for benzoyl metronidazole and may improve its oral bioavailability.
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spelling pubmed-37326342013-08-22 Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole Huang, Qing Li, Benpeng Yang, Shuo Ma, Peipei Wang, Zhizhong ScientificWorldJournal Research Article A one-pot method for the preparation of benzoyl metronidazole was achieved by using N,N′-carbonyldiimidazole as a coupling reagent. Moreover, it was found that the byproduct imidazole as the catalyst promoted the reaction. In addition, the β-cyclodextrin solubilization of benzoyl metronidazole was investigated by phase-solubility method. The phase-solubility studies indicated that the solubility of benzoyl metronidazole (S = 0.1435 g/L) was substantially increased 9.7-fold (S′ = 1.3881 g/L) by formation of 1 : 1 benzoyl metronidazole/β-cyclodextrin complexes in water, and the association constant K (a) value was determined to be 251 (±23) dm(3)/mol. Therefore, β-cyclodextrin can work as a pharmaceutical solubilizer for benzoyl metronidazole and may improve its oral bioavailability. Hindawi Publishing Corporation 2013-07-21 /pmc/articles/PMC3732634/ /pubmed/23970831 http://dx.doi.org/10.1155/2013/306476 Text en Copyright © 2013 Qing Huang et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Huang, Qing
Li, Benpeng
Yang, Shuo
Ma, Peipei
Wang, Zhizhong
Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title_full Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title_fullStr Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title_full_unstemmed Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title_short Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole
title_sort preparation and cyclodextrin solubilization of the antibacterial agent benzoyl metronidazole
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3732634/
https://www.ncbi.nlm.nih.gov/pubmed/23970831
http://dx.doi.org/10.1155/2013/306476
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