Miconazole nitrate
[CAS# 22832-87-7]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Antifungal drugs
• Name: Miconazole nitrate
• Synonyms: 1-(2,4-Dichloro-beta-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole nitrate
• Molecular Formula: C₁₈H₁₄Cl₄N₂O.HNO₃
• Molecular Weight: 479.15
• CAS Registry Number: 22832-87-7 (75319-48-1)
• EC Number: 245-256-6
• SMILES: C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H317-H319-H410
• Safety Statements: P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P333+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H410
Germ cell mutagenicity	Muta.	2	H341
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

Miconazole nitrate is an antifungal medication belonging to the imidazole class of compounds. It is the nitrate salt form of miconazole, a synthetic imidazole derivative characterized by its broad-spectrum antifungal activity. The molecular structure consists of an imidazole ring substituted with various functional groups that confer both lipophilicity and antifungal potency, while the nitrate ion provides enhanced water solubility for pharmaceutical formulations.

Miconazole was first developed in the late 1960s and introduced for clinical use in the 1970s. The nitrate salt form became widely used due to its improved stability and solubility compared to the free base, facilitating topical and systemic delivery. Since its introduction, miconazole nitrate has been extensively employed in the treatment of superficial fungal infections.

The mechanism of action of miconazole nitrate involves the inhibition of fungal cytochrome P450-dependent enzyme lanosterol 14α-demethylase. This enzyme is essential for the biosynthesis of ergosterol, a key component of fungal cell membranes. By blocking ergosterol synthesis, miconazole nitrate disrupts membrane integrity, increasing membrane permeability and leading to fungal cell death. This mechanism imparts selective toxicity against fungi while sparing human cells, which utilize cholesterol instead of ergosterol.

Miconazole nitrate is effective against a broad range of fungal species, including dermatophytes, yeasts such as Candida spp., and some molds. It is commonly prescribed for cutaneous candidiasis, tinea infections (ringworm, athlete’s foot, jock itch), and mucocutaneous candidiasis. Additionally, it shows activity against certain gram-positive bacteria, contributing to its utility in mixed infections.

Pharmaceutical formulations of miconazole nitrate include topical creams, ointments, powders, sprays, and vaginal suppositories. The nitrate salt’s water solubility enables the preparation of stable, easy-to-apply formulations suitable for localized treatment. Dosages and treatment duration depend on infection type and severity.

The compound is generally well tolerated, with adverse effects mostly limited to localized irritation, burning, or itching at the application site. Systemic side effects are rare due to minimal systemic absorption when applied topically. Caution is advised in patients with known hypersensitivity to imidazole antifungals.

Miconazole nitrate’s stability profile permits storage at room temperature under dry conditions, with typical shelf lives of two to three years depending on formulation. It is incompatible with strong oxidizing agents and acidic conditions that may degrade the active compound.

In addition to human medicine, miconazole nitrate is used in veterinary medicine for the treatment of fungal infections in animals. Its broad antifungal spectrum and safety profile make it a valuable therapeutic agent in multiple species.

Overall, miconazole nitrate is a well-established antifungal agent whose clinical use spans several decades. Its potent inhibition of ergosterol synthesis, broad antimicrobial spectrum, and favorable formulation characteristics contribute to its continued prominence in treating superficial fungal infections in humans and animals.