Clotrimazole | Imidazole Antifungal | CAS 23593-75-1

Product Name: Clotrimazole
CAS No.: 23593-75-1
Chemical Name: 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
Molecular Formula: C₂₂H₁₇ClN₂
Appearance: White or pale yellow crystalline powder
Solubility: Practically insoluble in water; soluble in ethanol, chloroform, and dimethylformamide
Stability: Stable under normal storage conditions

1. Introduction

Clotrimazole is a synthetic antifungal agent from the imidazole derivative group for topical use. It possesses a broad spectrum of antimycotic activity. Its mechanism of action involves disruption of ergosterol synthesis, a component of the fungal cell membrane, leading to membrane damage.

Fungal infections of the skin and mucous membranes (mycoses) are a common problem in dermatology and gynecology. Clotrimazole, due to its high efficacy against most pathogenic fungi causing superficial mycoses and its good tolerability, has become one of the most frequently used drugs for their treatment.

2. Chemical Structure & Synthesis

The molecule consists of an imidazole ring linked to a triphenylmethane group, where one of the phenyl radicals is substituted with a chlorine atom.

Synthesis: Clotrimazole is synthesized by reacting chloro-trityl chloride (a product of the reaction of benzotrichloride with chlorobenzene) with imidazole in the presence of a base.

3. Mechanism of Action

Clotrimazole inhibits the fungal cell enzyme cytochrome P450-dependent 14α-demethylase, which is involved in the conversion of lanosterol to ergosterol. Disruption of ergosterol synthesis leads to changes in the structure and function of the fungal cell membrane, increased permeability, and ultimately cell lysis. At high concentrations, it may exert fungicidal action by damaging mitochondrial and peroxisomal enzymes.

4. Antimicrobial Spectrum

Active against:

• Dermatophytes (Trichophyton, Epidermophyton, Microsporum)

• Yeast and mold fungi (Candida, Aspergillus)

• Tinea versicolor causative agent (Malassezia furfur)

• Some Gram-positive bacteria (Streptococcus, Staphylococcus)

• Trichomonas vaginalis

5. Applications

Clotrimazole is applied topically in the form of creams, ointments, solutions, vaginal tablets, and suppositories for the treatment of:

• Dermatophytoses caused by dermatophytes (tinea pedis, tinea manuum, tinea corporis, tinea cruris)

• Candidiasis of the skin and mucous membranes (vulvovaginitis, balanitis, oral candidiasis)

• Tinea versicolor (pityriasis versicolor)

• Erythrasma

6. Conclusion

Clotrimazole is an effective and widely used antifungal drug for the topical treatment of various mycoses of the skin and mucous membranes. Its broad spectrum of action, ease of use, and relatively low incidence of side effects make it an important tool in the arsenal of dermatologists and gynecologists.