Sublimation thermodynamics of four fluoroquinolone antimicrobial compounds

Blokhina, Svetlana V.; Sharapova, Angelica; Ol’khovich, Marina V.; Perlovich, German L.

doi:10.1016/j.jct.2016.10.010

Cited by 28 publications

(12 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This precondition has been thoroughly followed when selecting experimental data from literature. Again, as in the previous section, the main contribution of experimental sublimation values has been provided by the compendium of Acree, Jr. et al [ 8 ], supplemented by a number of later publications, referencing the heat of sublimation of acetophenones [ 23 ], substituted benzamides [ 26 ], crown ethers [ 29 ], long-chain fluorinated alcohols [ 33 ], halogenated fluorenes [ 35 ], tricyclic nitrogen heteroaromatics [ 42 ], polyphenylbenzenes [ 47 ], adamantylideneadamantane [ 48 ], cyclic N , N ′-thioureas [ 49 ], indole-3-carboxylic acids [ 50 ], vanillyl alcohol [ 51 ], alkanoylphenols [ 52 ], adamantanes [ 53 ], six-membered ring aliphatics [ 54 ], fluoroquinolones [ 55 ], oxazolidinones [ 56 ], nitrogen-containing substituted adamantanes [ 57 ], 2,7-di- t -butylfluorene [ 58 ] and nitroimidazoles [ 59 ].…”

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

“…This precondition has been thoroughly followed when selecting experimental data from literature. Again, as in the previous chapter, the main contribution of experimental sublimation values has been provided by the compendium of W. E. Acree Jr. et al [8], supplemented by a number of later publications, referencing the heat of sublimation of acetophenones [23], substituted benzamides [26], crown ethers [29], long-chain fluorinated alcohols [33], halogenated fluorenes [35], tricyclic nitrogen heteroaromatics [42], polyphenylbenzenes [47], adamantylideneadamantane [48], cyclic N,N'-thioureas [49], indole-3-carboxylic acids [50], vanillyl alcohol [51], alkanoylphenols [52], adamantanes [53], six-membered ring aliphatics [54], fluoroquinolones [55], oxazolidinones [56], nitrogen-containing substituted adamantanes [57], 2,7-di-t-butylfluorene [58] and nitroimidazoles [58]. (row B and F at the bottom of Table 2) exhibit a higher scatter of the experimental data in comparison with the heat-of-vaporization data.…”

Section: Enthalpy Of Sublimationmentioning

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

“…Принимая во внимание высокую значимость в медицинской практике препаратов фторхинолоновый группы, связанную с широтой их антимикробного спектра, представляет интерес разработка новых лекарственных форм этих препаратов или модификация структуры активного компонента для возможного снижения количества побочных эффектов. Одним из перспективных направлений развития является получение соосажденных солей уже известных соединений с органическими кисло-тами: адипиновой, фумаровой, малеиновой [44][45][46][47] или метансульфоновой, глюконовой, гликолевой [48]. Российским научным фондом в 2014-2016 гг.…”

Section: Discussionunclassified

“…был реализован проект 8 по изучению физико-химических свойств и разработке технологии получения смешанных кристаллов некоторых фармацевтических субстанций, в том числе ципрофлоксацина. Хорошая растворимость вновь полученных соединений обеспечивает их достаточно высокую биодоступность, а устойчивость к высоким температурам обеспечивает стабильность препарата при хранении и снижает вероятность образования полиморфных модификаций, являющихся частой причиной небиоэквивалентности воспроизведенных препаратов [45,47]. Другими авторами сопоставимые результаты были получены для ципрофлоксацина мезилата, ципрофлоксацина глюконата и ципрофлоксацина гликолята [48].…”

Section: Discussionunclassified

Fluoroquinolone antibiotics: safety of use by the example of ciprofloxacin

Молчан¹,

Смирнова²,

Вельц³

et al. 2019

Bezopasnost' i risk farmakoterapii

View full text Add to dashboard Cite

Резюме. В связи с повторяющимися сообщениями о побочных эффектах при применении антибиотиков фторхинолоновой группы эти препараты вновь и вновь становятся объектом пристального внимания специалистов фармаконадзора и врачей. Цель работы: изучение частоты и характера нежелательных реакций, связанных с применением препарата ципрофлоксацин, на основе анализа спонтанных сообщений, поступивших в российскую службу фармаконадзора. Материалы и методы: проведен ретроспективный анализ спонтанных сообщений о препарате ципрофлоксацин за период с 2008 по 2018 г. по базе данных «Фармаконадзор» автоматизированной информационной системы Росздравнадзора. Результаты: всего было зарегистрировано 3403 нежелательные реакции, возникшие у 2083 пациентов при применении ципрофлоксацина. Чаще всего развивались реакции со стороны кожи и подкожных тканей (37,3 %), общие расстройства и нарушения в месте введения (21,1 %), реакции со стороны желудочно-кишечного тракта (14,9 %). Более трети сообщений содержали информацию о серьезных нежелательных реакциях. Были выявлены непредвиденные реакции, не зафиксированные в инструкции по медицинскому применению ципрофлоксацина: брадикардия, предсердная аритмия, цианоз, повышение артериального давления. Выводы: антибиотики фторхинолонового ряда с доказанной эффективностью и многолетним опытом клинического применения продолжают оставаться препаратами, безопасность которых требует постоянного контроля. Результаты исследования подтвердили возможность выявления широкого спектра нежелательных реакций методом спонтанных сообщений. Регуляторным органам Российской Федерации целесообразно рекомендовать держателям регистрационных удостоверений внести в инструкцию по медицинскому применению ципрофлоксацина информацию о нежелательных реакциях, которые были зарегистрированы в постмаркетинговый период. Ключевые слова: ципрофлоксацин; фторхинолоновые антибиотики; нежелательные реакции; фармаконадзор; безопасность лекарств

show abstract

Sublimation thermodynamics of four fluoroquinolone antimicrobial compounds

Cited by 28 publications

References 41 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

Fluoroquinolone antibiotics: safety of use by the example of ciprofloxacin

Contact Info

Product

Resources

About