47447-52-9

Basic information

• Product Name: (S)-Miconazole
• Synonyms: (S)-Miconazole;1H-Imidazole, 1-[(2S)-2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]- (9CI);1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-, (S)-
• CAS NO: 47447-52-9
• Molecular Formula: C18H14 Cl4 N2 O
• Molecular Weight: 0
• Mol File: 47447-52-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Miconazole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Miconazole(47447-52-9)
• EPA Substance Registry System: (S)-Miconazole(47447-52-9)

Safety Data

• Hazardous Substances Data: 47447-52-9(Hazardous Substances Data)

Usage

General Description

(S)-Miconazole is an antifungal medication classified as an imidazole derivative. It works by inhibiting the synthesis of ergosterol, an essential component of the fungal cell membrane, leading to the disruption of the cell membrane and ultimately the death of the fungal organism. This medication is commonly used to treat various fungal infections such as athlete's foot, jock itch, ringworm, and yeast infections. It is available in various formulations including cream, powder, and spray for topical application, as well as oral gel for treatment of oral thrush. (S)-Miconazole is generally well-tolerated and effective in treating fungal infections, although it may cause side effects such as skin irritation or itching at the application site. Overall, it is a widely used and effective antifungal medication.

Upstream product

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• 27656-21-9 (R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol 
• 20443-99-6 2,4-dichlorobenzyl bromide 
• 141394-11-8 (S)-2-(2,4-dichlorophenyl)oxirane 
• 1278521-19-9 (S)-2-chloro-1-(2,4-dichlorophenyl)ethyl chloroacetate 

Downstream Products

• 1581279-28-8 [(η⁶-p-cymene)RuCl(miconazole)₂]Cl 

Relevant articles and documents

Development of stability indicating HPLC method for the separation and validation of enantiomers of miconazole

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.

Use of miconazole and derivatives thereof as TGR5 agonists (by machine translation)

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)

Anti-staphylococcal biofilm activity of miconazoctylium bromide

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.