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

Description

(S)-Miconazole, an imidazole derivative, is an antifungal medication that functions by inhibiting the synthesis of ergosterol, a vital component of the fungal cell membrane. This action leads to the disruption of the cell membrane and the eventual death of the fungal organism. It is recognized for its effectiveness in treating a range of fungal infections and is generally well-tolerated by patients.

Uses

Used in Pharmaceutical Industry:
(S)-Miconazole is used as an antifungal agent for treating various fungal infections such as athlete's foot, jock itch, ringworm, and yeast infections. Its ability to disrupt the fungal cell membrane makes it a potent medication in combating these conditions.
Used in Topical Medication:
(S)-Miconazole is used as a topical treatment in the form of cream, powder, and spray to directly target fungal infections on the skin. This application method allows for localized treatment and minimizes systemic side effects.
Used in Oral Health:
(S)-Miconazole is used as an oral gel for the treatment of oral thrush, a fungal infection that affects the mouth and throat. Its antifungal properties help to eliminate the infection and alleviate associated symptoms.
Used in Patient Care:
(S)-Miconazole is used to improve the quality of life for patients suffering from fungal infections by providing an effective and well-tolerated treatment option. Its various formulations cater to different preferences and application needs, ensuring accessibility and convenience for users.

Upstream product

• 94-99-5 2,4-Dichlorobenzyl chloride 
• 24155-42-8 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol 
• 22916-47-8 miconazole 
• 46503-52-0 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 1777-82-8 (2,4-dichlorophenyl)methanol 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 13692-15-4 2-(2,4-dichlorophenyl)oxirane 
• 62566-67-0 (R)-2-(2,4-dichlorophenyl)oxirane 
• 114446-57-0 (R)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol 
• 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.