A favourable solubility of isoniazid, an antitubercular antibiotic drug, in alternative solvents

Forte, Andreia; Melo, Catarina I.; Bogel‐Łukasik, Rafał; Bogel‐Łukasik, Ewa

doi:10.1016/j.fluid.2012.01.022

Cited by 81 publications

(57 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…How well do the predictions of Equation (2) compare to experimental heat-of-fusion data? In order to answer this question more than 1200 experimental values have been inserted into the database, taken from Acree’s compendium publication [ 8 ], complemented by recent values for crown ethers [ 29 ], fluorinated alcohols [ 33 ], adamantanes [ 53 ], 2-chloro-3-(trifluoromethyl)pyridine [ 61 ], cyanatophenyl derivatives [ 62 ], diphenylamines [ 63 ], fatty acids [ 64 ], pyridinecarbothioamides [ 65 ], isoniazid [ 66 ] and phenylthiazole-thione [ 67 ]. Figure 5 shows a comparison of the experimental with the predicted values, independently calculated by means of Equation (2).…”

Section: Resultsmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Molecules

View full text Add to dashboard Cite

The calculation of the standard enthalpies of vaporization, sublimation and solvation of organic molecules is presented using a common computer algorithm on the basis of a group-additivity method. The same algorithm is also shown to enable the calculation of their entropy of fusion as well as the total phase-change entropy of liquid crystals. The present method is based on the complete breakdown of the molecules into their constituting atoms and their immediate neighbourhood; the respective calculations of the contribution of the atomic groups by means of the Gauss-Seidel fitting method is based on experimental data collected from literature. The feasibility of the calculations for each of the mentioned descriptors was verified by means of a 10-fold cross-validation procedure proving the good to high quality of the predicted values for the three mentioned enthalpies and for the entropy of fusion, whereas the predictive quality for the total phase-change entropy of liquid crystals was poor. The goodness of fit (Q2) and the standard deviation (σ) of the cross-validation calculations for the five descriptors was as follows: 0.9641 and 4.56 kJ/mol (N = 3386 test molecules) for the enthalpy of vaporization, 0.8657 and 11.39 kJ/mol (N = 1791) for the enthalpy of sublimation, 0.9546 and 4.34 kJ/mol (N = 373) for the enthalpy of solvation, 0.8727 and 17.93 J/mol/K (N = 2637) for the entropy of fusion and 0.5804 and 32.79 J/mol/K (N = 2643) for the total phase-change entropy of liquid crystals. The large discrepancy between the results of the two closely related entropies is discussed in detail. Molecules for which both the standard enthalpies of vaporization and sublimation were calculable, enabled the estimation of their standard enthalpy of fusion by simple subtraction of the former from the latter enthalpy. For 990 of them the experimental enthalpy-of-fusion values are also known, allowing their comparison with predictions, yielding a correlation coefficient R2 of 0.6066.

show abstract

Section: Resultsmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Molecules

View full text Add to dashboard Cite

show abstract

“…In order to answer this question more than 1200 experimental values have been inserted into the database, originating from Acree's compendium publication [8], complemented by recent values for crown ethers [29], fluorinated alcohols [33], adamantanes [53], 2-chloro-3-(trifluoromethyl)pyridine [61], cyanatophenyl derivatives [62], diphenylamines [63], fatty acids [64], pyridinecarbothioamides [65], isoniazid [66] and phenylthiazole-thione [67]. Figure 5 shows the correlation of the experimental with the predicted values, calculated by means of Formula 2.…”

Section: Enthalpy Of Fusionmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Preprint

View full text Add to dashboard Cite

Abstract:The calculation of the standard enthalpies of vaporization, sublimation and solvation of organic molecules is presented using a common computer algorithm on the basis of a group-additivity method. The same algorithm is also shown to enable the calculation of their entropy of fusion as well as the total phase-change entropy of liquid crystals. The present method is based on the complete break-down of the molecules into their constituting atoms and their immediate neighbourhood; the respective calculations of the contribution of the atomic groups by means of the Gauss-Seidel fitting method is based on experimental data collected from literature. The feasibility of the calculations for each of the mentioned descriptors was verified by means of a 10-fold cross-validation procedure proving the good to high quality of the predicted values for the three mentioned enthalpies and for the entropy of fusion, whereas the predictive quality for the total phase-change entropy of liquid crystals was poor. The goodness of fit (Q 2 ) and the standard deviation (σ) of the cross-validation calculations for the five descriptors was as follows: 0.9641 and 4.56 kJ/mol (N=3386 test molecules) for the enthalpy of vaporization, 0.8657 and 11.39 kJ/mol (N=1791) for the enthalpy of sublimation, 0.9546 and 4.34 kJ/mol (N=373) for the enthalpy of solvation, 0.8727 and 17.93 J/mol/K (N=2637) for the entropy of fusion and 0.5804 and 32.79 J/mol/K (N=2643) for the total phase-change entropy of liquid crystals. The large discrepancy between the results of the two closely related entropies is discussed in detail. Molecules, for which both the standard enthalpies of vaporization and sublimation were calculable, enabled the estimation of their standard enthalpy of fusion by simple subtraction of the former from the latter enthalpy. For 990 of them the experimental enthalpy-of-fusion values are also known, allowing their comparison with predictions, yielding a correlation coefficient R 2 of 0.6066.

show abstract

“…In spite of the low stability and fast degradation when administered with other anti-tuberculosis drugs, [ 26 , 27 , 28 ] isoniazid continues to be an essential drug recommended by WHO to integrate different drug regimens to treat tuberculosis infections [ 23 ]. Some studies made with this drug showed an improvement of the isoniazid solubility by simple dissolution of API in different imidazolium-based ionic liquids, observing that the solubility of the isoniazid decreases with the increase of the alkyl chain in the ionic liquid cation [ 29 ]. Another approach reported in the literature to improve the physicochemical properties and stability of isoniazid is the use of cocrystals with isoniazid, combining with numerous conformers like p -hydroxybenzoic acid, [ 30 ] nicotinamide, [ 30 ] fumaric acid, [ 30 ] succinic acid, [ 30 ] vanillic acid, [ 27 ] ferulic acid, [ 27 ] caffeic acid [ 27 ], and resorcinol [ 27 ].…”

Section: Introductionmentioning

confidence: 99%

Organic Salts Based on Isoniazid Drug: Synthesis, Bioavailability and Cytotoxicity Studies

2020

View full text Add to dashboard Cite

Tuberculosis is one of the ten causes of morbidity and mortality worldwide caused by Mycobacterium tuberculosis complex. Some of the anti-tuberculosis drugs used in clinic studies, despite being effective for the treatment of tuberculosis, present serious adverse effects as well as poor bioavailability, stability, and drug-resistance problems. Thus, it is important to develop approaches that could provide shorter drug regimens, preventing drug resistance, toxicity of the antibiotics, and improve their bioavailability. Herein, we reported the use of organic salts based on the isoniazid drug, which can act as an organic cation combined with suitable organic anions such as alkylsulfonate-based (mesylate, R or S-Camphorsulfonate), carboxylate-based (glycolate, vanylate) and sacharinate. The synthesis, characterization, and cytotoxicity studies comparing with the original isoniazid drug have been performed. The possibility to explore dicationic salts seems promising in order to improve original bioavailability, and promote the elimination of polymorphic forms as well as higher stability, which are relevant characteristics that the pharmaceutical industry pursues.

show abstract

A favourable solubility of isoniazid, an antitubercular antibiotic drug, in alternative solvents

Cited by 81 publications

References 42 publications

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Organic Salts Based on Isoniazid Drug: Synthesis, Bioavailability and Cytotoxicity Studies

Contact Info

Product

Resources

About