Miconazole - 22916-47-8

Miconazole

Catalog Number: EVT-276215
CAS Number: 22916-47-8
Molecular Formula: C18H14Cl4N2O
Molecular Weight: 416.1 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description

Miconazole is a well-established antifungal agent commonly used to treat infections caused by various species of Candida and other fungi. Its broad-spectrum activity and the ability to target multiple fungal species make it a valuable drug in the clinical setting. The efficacy of miconazole is attributed to its interference with fungal cell membrane integrity and function, primarily through the inhibition of ergosterol biosynthesis, which is a critical component of the fungal cell membrane1234678910.

Applications in Various Fields

Medical Applications

Miconazole is widely used in the medical field for the treatment of fungal infections. It has been shown to possess potent activity against a variety of Candida strains, including those resistant to other antifungals such as fluconazole8. Its fungicidal activity extends to biofilms, which are notoriously difficult to treat due to their resistance to many antifungal agents7.

Pharmaceutical Formulation Improvements

Recent studies have focused on improving the bioavailability and efficacy of miconazole through novel drug delivery systems. Miconazole-loaded solid lipid nanoparticles (MN-SLNs) have been developed to enhance oral bioavailability and antifungal activity, showing promising results in both in vitro and in vivo studies5. Transfersomal formulations have also been explored to improve skin permeability and provide effective treatment for cutaneous fungal infections10.

Biochemical Research

Miconazole has been used as a tool in biochemical research to study the effects of ergosterol biosynthesis inhibition on fungi. It has provided insights into the role of cell membrane components and their biosynthetic pathways in fungal growth and survival134. Additionally, the drug's impact on cellular processes such as respiration, cell permeability, and enzyme activity has been extensively studied, contributing to a better understanding of fungal physiology and the mechanism of action of antifungal agents249.

Properties

CAS Number

22916-47-8

Product Name

Miconazole

IUPAC Name

1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole

Molecular Formula

C18H14Cl4N2O

Molecular Weight

416.1 g/mol

InChI

InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2

InChI Key

BYBLEWFAAKGYCD-UHFFFAOYSA-N

SMILES

C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

Solubility

7.63e-04 g/L

Synonyms

Brentan
Dactarin
Miconasil Nitrate
Miconazole
Miconazole Nitrate
Monistat
Nitrate, Miconasil
Nitrate, Miconazole
R 14,889
R-14,889
R14,889

Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
Mechanism of Action

Miconazole acts by disrupting the synthesis of ergosterol, an essential component of the fungal cell membrane. It inhibits the enzyme lanosterol 14α-demethylase, leading to the accumulation of toxic methylated sterol precursors and a subsequent decrease in ergosterol levels1. This disruption in membrane synthesis results in increased membrane permeability and leakage of cellular contents2. Additionally, miconazole has been shown to inhibit the mitochondrial ATPase, which may contribute to its antifungal effects, particularly during growth on non-fermentable carbon sources9. Furthermore, miconazole can induce the production of reactive oxygen species (ROS), which can lead to oxidative damage and cell death67. It also affects the actin cytoskeleton, which is linked to ROS induction and may play a role in its antifungal activity6.

Method of Synthesis or Extraction
Miconazole can be synthesized by various methods, including the reaction of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone with m-chloroperbenzoic acid or by reacting 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone with sodium azide followed by reduction with lithium aluminum hydride. The yield and efficiency of each method vary, with the first method yielding a higher percentage of miconazole. However, the use of m-chloroperbenzoic acid in the synthesis process raises environmental and safety concerns due to its potential toxicity. Therefore, the second method is preferred due to its lower environmental impact and safety considerations.
Chemical Structure and Biological Activity
Miconazole has a chemical formula of C18H14Cl4N2O and a molecular weight of 416.13 g/mol. Its chemical structure consists of an imidazole ring, a dichlorophenyl group, and an ethylene bridge. Miconazole exerts its antifungal activity by inhibiting the synthesis of ergosterol, a vital component of fungal cell membranes. This inhibition leads to the disruption of the fungal cell membrane, resulting in cell death. Miconazole also exhibits antibacterial and antiviral properties, making it a broad-spectrum antifungal agent.
Biological Effects
Miconazole has been shown to have various biological effects on cell function and signal transduction. It has been reported to inhibit the growth of various fungi, including Candida albicans, Aspergillus fumigatus, and Trichophyton mentagrophytes. Miconazole has also been shown to have potential therapeutic effects in the treatment of various fungal infections, such as oral thrush, vaginal yeast infections, and ringworm. However, miconazole may also have potential toxic effects, including liver damage, allergic reactions, and drug interactions.
Future Perspectives and Challenges
Despite its potent antifungal properties, miconazole has several limitations in its use and study. These limitations include its potential toxic effects, drug interactions, and the emergence of drug-resistant fungal strains. To overcome these challenges, researchers are exploring new formulations and delivery methods for miconazole, such as nanoparticles and liposomes. Additionally, researchers are investigating the use of miconazole in combination with other antifungal agents to enhance its efficacy and reduce the risk of drug resistance.
Conclusion:
Miconazole is a potent antifungal agent that has various applications in medical, environmental, and industrial research. Its chemical structure and mechanism of action make it a broad-spectrum antifungal agent with potential therapeutic effects in the treatment of various fungal infections. However, the use of miconazole raises environmental and safety concerns, and proper precautions must be taken to ensure worker safety. Future research is needed to overcome the limitations of miconazole and to explore its potential in combination with other antifungal agents.

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