The imidazole antimycotic miconazole was first synthesized at Janssen Pharmaceuticals. Miconazole is barely soluble in water (0.3 mg/mL) and slightly soluble to soluble in the many organic solvents and dilute inorganic acids.

Trade Names

Andergin (Pierell), Brentan (Janssen), Daktar (Janssen), Daktarin (Abic, Edward Keller, Janssen), Dumicoat (Dumex), Femeron (Janssen), Micofim (Elofar), Micotar (Dermapharm), Micotef (LPB), Monistat (Cilag, Ethnor, Janssen), Monistat I.V. (Janssen), Vodol (Searle).

Synthesis

The synthesis begins with 2,4-dichloroacetophenone, which is first brominated to form the phenacyl bromide and then treated with imidazole to form the phenacylimidazole. Reduction with sodium borohydride and reaction of the resulting alcohol with 2,4-dichlorobenzyl chloride yields miconazole.

Indications

Especially topical therapy of skin infections caused by dermatophytes and yeasts, and mucocutaneous infections including Candida vulvovaginitis. Systemic, intravenous therapy especially of infections caused by Pseudoallescheria boydii (dosage up to 1.2 g 3 × per day) . For treatment of other generalized mycoses, mostly the newer, more effective, and less toxic azole antimycotics for systemic use, such as fluconazole and itraconazole, are indicated.

Side Effects

Multiple side effects have been observed after intravenous infusion of miconazole, which seem to be partly due to the formulation of the solvent, which contains the detergent Cremophor EL; mostly anaphylactic reactions, pruritus, dizziness, tachyarrhythmia, hyperaggregation of erythrocytes, anemia, thromocytosis, phlebitis, nausea, vomiting, hyperlipidemia, hyponatriemia, arthralgia, and flush.