Protonation and β-cyclodextrin complex formation equilibria of fluconazole

Orgován, Gábor; Kelemen, Hajnal; Noszál, Béla

doi:10.1007/s10847-016-0595-2

Cited by 17 publications

(11 citation statements)

References 5 publications

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“…A nuclear magnetic resonance (NMR) spectroscopic study was published in order to evaluate the complexation of fluconazole with β-CD, and the results confirmed the formation of an inclusion complex in aqueous solution [23,24]. Complexes of BFZ and miconazole prepared with different CDs by various methods such as kneading, co-evaporation, and physical mixing were characterized by Fourier transform infrared spectroscopy (FTIR) and DSC studies, and the effect of complexationon the dissolution rate of BFZ was studied [25,26].…”

Section: карактеризација на инклузиони комплекси меѓу бифоназол и разmentioning

confidence: 90%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

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The aim of this study is to confirm the formation of inclusion complexes between bifonazole (BFZ) and different cyclodextrin (CD) derivatives. BFZ, an imidazole antifungal derivative, is a very hydrophobic compound, which is a major drawback in obtaining topical pharmaceutical formulations with optimal bioavailability. CDs may increase local drug delivery by enhancing the drug release and/or permeation. Several native and derivatized CD derivatives were tested in the experiments. The binary systems between BFZ and CDs were prepared in two molar ratios by physical mixing methods. The physicochemical properties of these complexes were studied by differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy methods. The results showed favorable molecular interaction between the components in solid state and in solution. 1 H NMR-CD titrations and molecular modeling study showed that the most stable complex was obtained when using γ-CD. The Job's method and 2D NMR spectroscopy support the 2 : 1 stoichiometry of the BFZ : γ-CD complex.Keywords: bifonazole; cyclodextrins; differential scanning calorimetry; Fourier transform infrared spectroscopy; H NMR-CD titrations КАРАКТЕРИЗАЦИЈА НА ИНКЛУЗИОНИ КОМПЛЕКСИ МЕЃУ БИФОНАЗОЛ И РАЗЛИЧНИ ЦИКЛОДЕКСТРИНИ ВО ЦВРСТА СОСТОЈБА И ВО РАСТВОРЦелта на ова истражување е да се потврди образувањето на инклузиони комплекси меѓу бифоназол (BFZ) и различни циклодекстрински (CD) деривати. BFZ, кој претставува имидазолски фунгициден дериват, е силно хидрофобно соединение, што претставува голем недостаток при добивање топични фармацевтски препарати со оптимална биорасположливост. CD може да ја зголеми локалната испорака на лекот со подобрување на ослободувањето и/или пропустливоста на лекот. Експериментално беа тестирани неколку нативни и дериватизирани CD. Бинарните системи меѓу BFZ и CD беа подготвени во два моларни односа со методи на физичко мешање. Физичкохемиските својства на овие комплекси беа испитувани со диференцијална скенирачка калориметрија (DSC), Фуриеова трансформна инфрацрвена (FTIR) спектроскопија и со нуклеарно-магнетни резонантни спектроскопски методи. Резултатите покажуваат позитивна молекулска интеракција меѓу компонентите во цврста фаза и во раствор. Титрациите на 1 H NMR-CD и испитувањето со молекулско моделирање покажуваат дека најстабилен комплекс се добива со

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Section: карактеризација на инклузиони комплекси меѓу бифоназол и разmentioning

confidence: 90%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

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“…An NMR spectroscopic study was published in order to evaluate the complexation of fluconazole with β-CD, the results confirmed the formation of an inclusion complex in aqueous solution [19][20]. Complexes of fluconazole and bifonazole, miconazole, voriconazole prepared with different CDs by various methods such as kneading, co-evaporation, physical mixing and spray-dried were characterized by Fourier transform infrared spectroscopy (FT-IR) and DSC studies; the effect of complexation on the dissolution rate of MNZ was studied [21][22][23].…”

Section: Introductionmentioning

confidence: 75%

Characterization of Inclusion Complexes between Miconazole and Different Cyclodextrin Derivatives

Kelemen

Hancu

Gâz-Florea

et al. 2018

Acta Medica Marisiensis

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Objective: Miconazole, an imidazole antifungal derivative, is a very hydrophobic compound, a major drawback in obtaining topical pharmaceutical formulations with optimal bioavailability. Cyclodextrins (CDs) may increase local drug delivery by enhancing the drug release and/or permeation. The aim of the study is the characterization of inclusion complexes between miconazole and different CD derivatives. Methods: Several CD derivatives were tested in the experiments. The binary systems between miconazole and different CDs were prepared in 1:1 molar ratios by physical-mixture and kneading methods. Differential scanning calorimetry (DSC) and Fourier transformed-infrared spectroscopy (FT-IR) methods were used to characterize solid state interactions between miconazole and CDs in their binary systems. Results: The FT-IR analysis suggests the formation of a new solid phase, indicating a molecular interaction between the components. The DSC analysis sustains the hypothesis of formation of partial inclusion complexes between miconazole nitrate and CD. Conclusion: The thermic behaviour of the complexes depends both on the preparation method and the composition of the products.

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“…Stability constants ( K ) of the inclusion complexes were calculated by non‐linear parameter fitting of Eq. to the δ obs versus [CD] T datasets using OriginPro 8 program based on previous works .…”

Section: Methodsmentioning

confidence: 99%

Chiral separation of rasagiline using sulfobutylether‐β‐cyclodextrin: capillary electrophoresis, NMR and molecular modeling study

et al. 2019

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Pressure‐assisted stereospecific capillary electrophoresis method was developed for the determination of enantiomeric purity of the antiparkinsonian agent (R)‐rasagiline. The optimized method, 50 mM glycine‐HCl buffer pH 2, supplied with 30 mM sulfobutylether‐β‐cyclodextrin, at 35°C, applying 12 kV in reversed polarity, and –8 mbar pressure (vacuum), short‐end injection with ‐25 mbar × 2 s, was successful for baseline separation of rasagiline enantiomers (Rs = 3.5 ± 0.1) in a short analysis time. The method was validated according to current guidelines and proved to be reliable, linear, precise and accurate for determination of 0.15% S‐enantiomer as chiral impurity in R‐rasagiline sample, as well as quantification of the eutomer. Method application was tested on a commercial tablet formulation. Determination of spatial structure of diastereomeric associates was based on 1H and 2D ROESY NMR, indicating that the aromatic moiety of the molecule can enter the cyclodextrin cavity. NMR titration and molecular modeling revealed that S‐rasagiline formed a more stable inclusion complex with sulfobutylether‐β‐cyclodextrin, than its antipode, which is in agreement with electrophoretic results.

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Protonation and β-cyclodextrin complex formation equilibria of fluconazole

Cited by 17 publications

References 5 publications

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Characterization of Inclusion Complexes between Miconazole and Different Cyclodextrin Derivatives

Chiral separation of rasagiline using sulfobutylether‐β‐cyclodextrin: capillary electrophoresis, NMR and molecular modeling study

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