Antimycotic sterol biosynthesis inhibitors

Berg, Dieter; Büchel, Karl Heinz; Plempel, M.; Regel, E.

doi:10.1016/0165-6147(86)90330-5

Cited by 24 publications

(17 citation statements)

References 18 publications

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“…It possesses a broad spectrum of activity in vitro against dermatophytes, molds, yeasts, dimorphic fungi, and some Gram-positive bacteria [1]. It has a double mechanism of action as it works by preventing the 14-α-demethylation of 24-methylenedihydrolanosterol, consequently preventing the formation of the cellular membrane by inhibiting the production of ergosterol, and also causes direct damage to the membrane [2]. It also shows an antiinflammatory effect on erythema caused by histamine [3,4].…”

Section: карактеризација на инклузиони комплекси меѓу бифоназол и разmentioning

confidence: 99%

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: 99%

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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“…In so doing the drawbacks arising from optically impure reagents or different rates of formation of the diastereoisomers are avoided. Because patients with acquired immunodeficiency syndrome or undergoing anti-cancer chemotherapy or organ transplants are susceptible to bacterial and fungal diseases, new classes of antifungal drugs have been developed since 1970 and in particular, novel antifungal agents, imidazole and triazole derivatives, some of which contain stereogenic centres [7,8]. In some cases the individual isomers of these compounds differ in their pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

Direct resolution of a new antifungal agent, voriconazole (UK-109,496) and its potential impurities, by use of coupled achiral-chiral high-performance liquid chromatography

et al. 1998

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Key WordsColumn liquid chromatography Enantiomer separation Voriconazole (UK-109,496) Effect of organic mobile-phase modifier SummaryCoupled achiral-chiral high-performance liquid chromatography (HPLC) with an achiral amino-based column coupled with a chiral amylose-based column has been used for qualitative and quantitative determination of the potential chiral and achiral impurities of Voriconazole (UK-109,496), a new antifungal agent with two stereogenic centres. The effect of the organic mobile-phase modifier, ethanol, was studied. The assay response was linearly dependent on concentration over the range 1.2-40.4 tag for Voriconazole and 2.5-104.0 ng for the impurities. The limit of detection was 2.5 ng for each analyte.

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“…This combination is thought to combine the well-documented antifungal activity of bifonazole [4,5] with the known keratoplastic effect of urea [6]. In numerous clinical trials, the efficacy of this ointment has been demonstrated [3].…”

Section: Introductionmentioning

confidence: 99%

Ultrastructural Changes in Onychomycosis during the Treatment with Bifonazole/Urea Ointment

Fritsch

Stettendorf

1992

Dermatology

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In the present study, we investigated the effects of bifonazole/urea ointment, a novel topical drug for the treatment of onychomycosis, on the ultrastructure of normal and fungus-infected human toenails by scanning electron microscopy. Nails were treated with the drug ex vivo and compared to untreated controls. During treatment, the corneocyte layers disintegrated, and the structure markedly loosened. After 5 days of treatment, the morphology of fungal cells, found at the undersurface of infected nails, was changed due to the antifungal drug action. The present data demonstrate that by the use of this drug, the agent effectively penetrates the nail plate and affects the fungal cells.

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Antimycotic sterol biosynthesis inhibitors

Cited by 24 publications

References 18 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

Direct resolution of a new antifungal agent, voriconazole (UK-109,496) and its potential impurities, by use of coupled achiral-chiral high-performance liquid chromatography

Ultrastructural Changes in Onychomycosis during the Treatment with Bifonazole/Urea Ointment

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