|Trade names||Desenex, Monistat, others|
|Topical, vaginal, sublabial|
|Bioavailability||<1% after topical application|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||416.127 g·mol−1|
|3D model (JSmol)|
Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot). It is applied to the skin or vagina as a cream or ointment.
Common side effects include itchiness or irritation of the area in which it was applied. Use in pregnancy is believed to be safe for the baby. Miconazole is in the imidazole family of medications. It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane.
Miconazole was patented in 1968 and approved for medical use in 1971. It is on the World Health Organization's List of Essential Medicines.
Miconazole is mainly used externally for the treatment of ringworm including jock itch and athlete's foot. Internal application is used for oral or vaginal thrush (yeast infection). This oral gel may also be used for the lip disorder angular cheilitis and other associated systems.
Mechanism of action
Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol. In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.
After application to the skin, miconazole can be measured in the skin for up to four days. Less than 1% is absorbed into the bloodstream, where 88.2% are bound to plasma proteins and 10.6% to blood cells. The substance is partly metabolized and mainly eliminated via the faeces.
The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.
Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.
Brands and formulations
Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):
- Oral gel 24 mg/ml (20 mg/g)
- Oravig 50 mg once daily buccal tablet:
In 2010, the U.S. Food and Drug Administration approved Oravig (miconazole) buccal tablets once daily for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older. Oravig is the only local, oral prescription formulation of miconazole approved for this use in the U.S.
External skin treatment (brand names Desenex and Zeasorb in US and Canada, Micatin, Monistat-Derm, Daktarin in India, UK, Australia, Belgium and the Philippines, Daktar in Norway, Fungidal in Bangladesh, Decocort in Malaysia)
- Topical cream: 2-5%
- Combination: hydrocortisone/miconazole cream with 1% and 2%, respectively (Daktacort in UK, Daktodor in Greece)
- Dusting powder: 2% powder with chlorhexidine hydrochloride (mycoDust)
Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):
- Pessaries: 200 or 100 mg
- Vaginal cream: 2% (7-day treatment), 4% (3-day treatment)
- Combination: 2% cream with either 100 or 200 mg
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