- Development of stability indicating HPLC method for the separation and validation of enantiomers of miconazole
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A selective and sensitive stability indicting HPLC method was developed for the analysis of enantiomers of miconazole. For this purpose, six different polysaccharide-based chiral columns were evaluated. Optimization was performed using several polar organic and alcohol-hydrocarbon mobile phases. As a result of optimization studies, the analysis was carried out using Lux Cellulose-3, methanol as a mobile phase at a flow rate of 1?mL·min?1, and the detection wavelength was arranged to 230?nm. Developed method has been fully validated according to International Council on Harmonization guidelines. Method was found linear in the concentration range of 1 to 200?μg·mL?1. Coefficient of determination (R2) was calculated as 0.9996, intraday precision of the method was found with the RSD% of 0.56, and the recovery of the method was calculated close to 100%. Furthermore, some other validation parameters like specificity, selectivity, LOD, and LOQ were also investigated. Stability indicating capability of this method was shown by forced degradation studies, and the run time for each analysis was less than 6?minutes. As a result, simple, fast, reliable HPLC method was developed for the separation and determination of the enantiomers of miconazole. Applicability of the developed method was shown with the application of marketed pharmaceutical preparations.
- Bounoua, Nadia,Sekkoum, Khaled,Gumustas, Mehmet,Belboukhari, Nasser,Ozkan, Sibel A.
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Read Online
- SMALL MOLECULE STIMULATORS OF THE CORE PARTICLE OF THE PROTEASOME
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This present disclosure relates to series compounds and methods of use for the treatment of a disease caused by abnormal regulation of the ubiquitin-proteasome system (UPS), and wherein said compound is an effective stimulator of the 20S core particle (CP) of the UPS. Composition matters and methods of uses are within the scope of this disclosure.
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Paragraph 00101
(2021/02/26)
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- Use of miconazole and derivatives thereof as TGR5 agonists (by machine translation)
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The invention belongs to the technical field of medicines, and relates to novel application TGR5 of miconazole and derivatives thereof in treatment, of diseases and conditions of a biological pathologic process involved in treatment, and. The miconazole and the analogues thereof can activate TGR5 active, for use TGR5 in the treatment or prevention of diseases associated with, activity modulation. (by machine translation)
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Paragraph 0031; 0036; 0037-0040
(2020/05/02)
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- Colistin sulfate chiral stationary phase for the enantioselective separation of pharmaceuticals using organic polymer monolithic capillary chromatography ?
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A new functionalized polymer monolithic capillary with a macrocyclic antibiotic, namely colistin sulfate, as chiral selector was prepared via the copolymerization of binary monomer mixtures consisting of glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in porogenic solvents namely 1-propanol and 1,4-butanediol, in the presence of azobisiso-butyronitrile (AIBN) as initiator and colistin sulfate. The prepared capillaries were investigated for the enantioselective nano-LC separation of a group of racemic pharmaceuticals, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistaminics, anticancer drugs, and antiarrhythmic drugs. Acceptable separation was achieved for many drugs using reversed phase chromatographic conditions with no separation achieved under normal phase conditions. Colistin sulfate appears to be useful addition to the available macrocyclic antibiotic chiral phases used in liquid chromatography.
- Fouad, Ali,Shaykoon, Montaser Sh.A.,Ibrahim, Samy M.,El-Adl, Sobhy M.,Ghanem, Ashraf
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- Anti-staphylococcal biofilm activity of miconazoctylium bromide
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We designed and synthesized miconazole analogues containing a substituted imidazolium moiety. The structural modification of the miconazole led to a compound with high potency to prevent the formation and disrupt bacterial biofilms, as a result of accumulation in the biofilm matrix, permeabilization of the bacterial membrane and generation of reactive oxygen species in the cytoplasm.
- Tessier, Jérémie,Golmohamadi, Mahmood,Wilkinson, Kevin J.,Schmitzer, Andreea R.
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p. 4288 - 4294
(2018/06/22)
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- HPLC method for separating enantiomers of imidazole derivatives - Antifungal compounds
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The aim of this study was to test separation possibility of enantiomers of nine active substances belonging to imidazole derivatives: bifonazole, butoconazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sertaconazole and tioconazole. The study was performed using HPLC method and the CHIRALCEL OJ column (10 μm; 250 × 4.6 mm), the mobile phase flow rate of 0.8 mL/min and detection at 220 nm. Mobile phases containing hexane and the following modifiers: alcohols (2-propanol, ethanol, methanol) and diethylamine were tested. At first isocratic elution was used but some enantiomers eluted after a long retention time and their peaks were asymmetrical and too wide. Therefore, a gradient elution was developed allowing to obtain satisfactory retention times and other parameters of enentioseparation of the compounds.
- Podolska, Marzena,Bia?ecka, Wanda,Kulik, Anna,Kwiatkowska-Puchniarz, Barbara,Mazurek, Aleksander
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p. 777 - 784
(2017/06/05)
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- METHOD FOR PRODUCING PULVERIZED ORGANIC COMPOUND PARTICLE
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Disclosed is a method for producing pulverized particles of a crystalline organic compound which is poorly water-soluble. Also disclosed is a pulverized organic compound particle produced by such a method. Specifically disclosed is a method for producing a poorly water-soluble organic compound particle for medical use, which is characterized in that a poorly water-soluble organic compound for medical use is mixed with a physiologically acceptable salt and a physiologically acceptable polyol, and subjected to wet milling. Also specifically disclosed is a poorly water-soluble organic compound particle for medical use, which is produced by such a production method.
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- Conventional chiralpak ID vs. capillary chiralpak ID-3 amylose tris-(3-chlorophenylcarbamate)-based chiral stationary phase columns for the enantioselective HPLC separation of pharmaceutical racemates
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A comparative enantioselective analysis using immobilized amylose tris-(3-chlorophenylcarbamate) as chiral stationary phase in conventional high-performance liquid chromatography (HPLC) with Chiralpak ID (4.6mm ID×250mm, 5μm silica gel) and micro-HPLC with Chiralpak ID-3 (0.30mm ID×150mm, 3μm silica gel) was conducted. Pharmaceutical racemates of 12 pharmacological classes, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, dopamine antagonists, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, diuretics, antihistaminics, anticancer drugs, and antiarrhythmic drugs were screened under normal phase conditions. The effect of an organic modifier on the analyte retentions and enantiomer recognition was investigated. Baseline separation was achieved for 1-acenaphthenol, carprofen, celiprolol, cizolirtine carbinol, miconazole, tebuconazole, 4-hydroxy-3-methoxymandelic acid, 1-indanol, 1-(2-chlorophenyl)ethanol, 1-phenyl-2-propanol, flavanone, 6-hydroxyflavanone, 4-bromogluthethimide, and pentobarbital on the 4.6mm ID packed with a 5μm silica column using conventional HPLC. Nonetheless, baseline separation was achieved for aminoglutethimide, naftopidil, and thalidomide on the 0.3mm ID packed with a 3μm silica capillary column. Chirality 26:677-682, 2014.
- Ahmed, Marwa,Gwairgi, Marina,Ghanem, Ashraf
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p. 677 - 682
(2015/03/31)
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- Asymmetric chemoenzymatic synthesis of miconazole and econazole enantiomers. the importance of chirality in their biological evaluation
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A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.
- Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Malpartida, Francisco,Gotor, Vicente
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p. 2115 - 2122
(2011/05/19)
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- Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC
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In our recent work, a series of dendritic chiral stationary phases (CSPs) were synthesized, in which the chiral selector was L-2-(p-toluenesulfonamido)-3- phenylpropionyl chloride (selector I), and the CSP derived from three-generation dendrimer showed the best separation ability. To further investigate the influence of the structures of dendrimer and chiral selector on enantioseparation ability, in this work, another series CSPs (CSPs 1-4) were prepared by immobilizing (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate (selector II) on one- to four-generation dendrimers that were prepared in previous work. CSPs 1 and 4 demonstrated the equivalent enantioseparation ability. CSPs 2 and 3 showed the best and poorest enantioseparation ability respectively. Basically, these two series of CSPs exhibited the equivalent enantioseparation ability although the chiral selectors were different. Considering the enantioseparation ability of the CSP derived from aminated silica gel and selector II is much better than that of the one derived from aminated silica gel and selector I, it is believed that the dendrimer conformation essentially impacts enantioseparation.
- He, Bao-Jiang,Yin, Chuan-Qi,Li, Shi-Rong,Bai, Zheng-Wu
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experimental part
p. 69 - 76
(2010/09/09)
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- New highly asymmetric henry reaction catalyzed by CuII and a C1-symmetric aminopyridine ligand, and its application to the synthesis of miconazole
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A new catalytic asymmetric Henry reaction has been developed that uses a C1 -symmetric chiral aminopyridine ligand derived from camphor and picolylamine. A variety of aromatic, heteroaromatic, aliphatic, and unsaturated aldehydes react with nit
- Blay, Gonzalo,Domingo, Luis R.,Hernandez-Olmos, Victor,Pedro, Jose R.
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experimental part
p. 4725 - 4730
(2009/05/07)
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