Miconazole
- BP-S-6-Medicinal Chemistry III
- Mar 31
- 1 min read
Chemical Structure / Formula of Miconazole
Formula: C18H14Cl4N2O
Structure: Imidazole antifungal with multiple chlorine substitutions.
Mechanism of Action
Inhibits ergosterol synthesis, disrupting fungal membrane stability.
Uses
Oral thrush, cutaneous fungal infections, vaginal candidiasis.
Side Effects
Skin irritation, burning, redness.
Synthesis of Miconazole
Structure-Activity Relationship (SAR) of Miconazole
Structural Feature | SAR Insight |
Imidazole ring | Essential for antifungal activity; interacts with fungal cytochrome P450 enzyme, inhibiting lanosterol 14α-demethylase. |
2,4-dichlorobenzyl group | Increases lipophilicity, allowing better membrane penetration. Chlorine enhances potency. |
Aromatic ring (phenyl) | Enhances binding to fungal enzymes. Substitutions affect selectivity and potency. |
Ether linkage (–O–CH₂–) | Improves flexibility and spatial orientation for optimal enzyme interaction. |
Bulky lipophilic side chains | Improve activity but may affect selectivity and toxicity. |
