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Pharmaceutics, volume 14, issue 9, pages 1881

Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study

Publication typeJournal Article
Publication date2022-09-06
Journal: Pharmaceutics
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.4
ISSN19994923
Pharmaceutical Science
Abstract

Formation thermodynamic parameters for three cocrystals of carbamazepine (CBZ) with structurally related coformers (benzamide (BZA), para-hydroxybenzamide (4-OH-BZA) and isonicotinamide (INAM)) were determined by experimental (cocrystal solubility and competitive reaction methods) and computational techniques. The experimental solubility values of cocrystal components at eutectic points and solubility product of cocrystals [CBZ + BZA], [CBZ + 4-OH-BZA], and [CBZ + INAM] in acetonitrile at 293.15 K, 298.15 K, 303.15 K, 308.15 K, and 313.15 K were measured. All the thermodynamic functions (Gibbs free energy, enthalpy, and entropy) of cocrystals formation were evaluated from the experimental data. The crystal structure of [CBZ + BZA] (1:1) cocrystal was solved and analyzed by the single crystal X-ray diffractometry. A correlation between the solubility products and pure coformers solubility values has been found for CBZ cocrystals. The relationship between the entropy term and the molecular volume of the cocrystal formation has been revealed. The effectiveness of the estimation of the cocrystal formation thermodynamic parameters, based on the knowledge of the melting temperatures of active pharmaceutical ingredients, coformers, cocrystals, as well as the sublimation Gibbs energies and enthalpies of the individual components, was proven. A new method for the comparative assessment of the cocrystal stability based on the H-bond propensity analysis was proposed. The experimental and theoretical results on the thermodynamic parameters of the cocrystal formation were shown to be in good agreement. According to the thermodynamic stability, the studied cocrystals can be arranged in the following order: [CBZ + 4-OH-BZA] > [CBZ + BZA] > [CBZ + INAM].

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GOST Copy
Manin A. N. et al. Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study // Pharmaceutics. 2022. Vol. 14. No. 9. p. 1881.
GOST all authors (up to 50) Copy
Manin A. N., Boycov D. E., Simonova O. R., Volkova T. V., Churakov A. V., Perlovich G. Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study // Pharmaceutics. 2022. Vol. 14. No. 9. p. 1881.
RIS |
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RIS Copy
TY - JOUR
DO - 10.3390/pharmaceutics14091881
UR - https://doi.org/10.3390%2Fpharmaceutics14091881
TI - Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study
T2 - Pharmaceutics
AU - Boycov, Denis E
AU - Simonova, Olga R
AU - Volkova, Tatyana V
AU - Manin, Alex N.
AU - Churakov, Andrei V.
AU - Perlovich, German
PY - 2022
DA - 2022/09/06 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 1881
IS - 9
VL - 14
PMID - 36145629
SN - 1999-4923
ER -
BibTex |
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BibTex Copy
@article{2022_Manin
author = {Denis E Boycov and Olga R Simonova and Tatyana V Volkova and Alex N. Manin and Andrei V. Churakov and German Perlovich},
title = {Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study},
journal = {Pharmaceutics},
year = {2022},
volume = {14},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {sep},
url = {https://doi.org/10.3390%2Fpharmaceutics14091881},
number = {9},
pages = {1881},
doi = {10.3390/pharmaceutics14091881}
}
MLA
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MLA Copy
Manin, Alex N., et al. “Formation Thermodynamics of Carbamazepine with Benzamide, Para-Hydroxybenzamide and Isonicotinamide Cocrystals: Experimental and Theoretical Study.” Pharmaceutics, vol. 14, no. 9, Sep. 2022, p. 1881. https://doi.org/10.3390%2Fpharmaceutics14091881.
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