Open Access
Pharmaceutics, volume 14, issue 11, pages 2276
The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy
2
Molecular Physical-Chemistry R&D Unit, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal
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Publication type: Journal Article
Publication date: 2022-10-24
Pharmaceutical Science
Abstract
Mefenamic acid has been used as a non-steroidal anti-inflammatory drug for a long time. However, its practical use is quite limited due to a number of side effects on the intestinal organs. Conformational polymorphism provides mefenamic acid with unique properties regarding possible modifications obtained during the micronization process, which can improve pharmacokinetics and minimize side effects. Micronization can be performed by decompression of supercritical fluids; methods such as rapid expansion of the supercritical solution have proven their efficiency. However, this group of methods is poorly applicable for compounds with low solubility, and the modification of the method using a pharmaceutically suitable co-solvent may be useful. In our case, addition of only 2 mol % dimethyl sulfoxide increased the solubility remarkably. Information on the conformational state may be critically important for carrying out micronization. In this work, structural analysis and estimate of conformational preferences of mefenamic acid in dimethyl sulfoxide − d6 (at 25 °C and 0.1 MPa) and in a mixed solvent supercritical carbon dioxide + dimethyl sulfoxide-d6 (45 °C, 9 MPa) were performed based on nuclear Overhauser effect spectroscopy. Results show changes in the conformation fractions depending on the medium used. The importance of allowing for hidden conformers in estimating the conformational state was demonstrated in the analysis. Obtained results may be useful for improving micronization parameters.
Citations by journals
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Journal of Molecular Liquids
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Journal of Molecular Liquids
3 publications, 25%
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Materials
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Materials
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International Journal of Molecular Sciences
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International Journal of Molecular Sciences
2 publications, 16.67%
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Polymers
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1 publication, 8.33%
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Journal of CO2 Utilization
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Journal of CO2 Utilization
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Membranes
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Membranes
1 publication, 8.33%
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Russian Journal of Physical Chemistry B
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Russian Journal of Physical Chemistry B
1 publication, 8.33%
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Citations by publishers
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
7 publications, 58.33%
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Elsevier
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Elsevier
4 publications, 33.33%
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Pleiades Publishing
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Pleiades Publishing
1 publication, 8.33%
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Belov K. V. et al. The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy // Pharmaceutics. 2022. Vol. 14. No. 11. p. 2276.
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Belov K. V., Batista de Carvalho L. A. E., Dyshin A. A., Efimov S., Khodov I. A. The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy // Pharmaceutics. 2022. Vol. 14. No. 11. p. 2276.
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TY - JOUR
DO - 10.3390/pharmaceutics14112276
UR - https://doi.org/10.3390%2Fpharmaceutics14112276
TI - The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy
T2 - Pharmaceutics
AU - Belov, Konstantin V.
AU - Batista de Carvalho, Luís A. E.
AU - Dyshin, Alexey A.
AU - Efimov, Sergey
AU - Khodov, Ilya A.
PY - 2022
DA - 2022/10/24 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 2276
IS - 11
VL - 14
SN - 1999-4923
ER -
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@article{2022_Belov,
author = {Konstantin V. Belov and Luís A. E. Batista de Carvalho and Alexey A. Dyshin and Sergey Efimov and Ilya A. Khodov},
title = {The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy},
journal = {Pharmaceutics},
year = {2022},
volume = {14},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {oct},
url = {https://doi.org/10.3390%2Fpharmaceutics14112276},
number = {11},
pages = {2276},
doi = {10.3390/pharmaceutics14112276}
}
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Belov, Konstantin V., et al. “The Role of Hidden Conformers in Determination of Conformational Preferences of Mefenamic Acid by NOESY Spectroscopy.” Pharmaceutics, vol. 14, no. 11, Oct. 2022, p. 2276. https://doi.org/10.3390%2Fpharmaceutics14112276.