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| Clinical data | |
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| Trade names | Monistat, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a601203 |
| License data | |
| Routes of administration | Topical,vaginal,sublabial |
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| Pharmacokinetic data | |
| Bioavailability | <1% after application to the skin |
| Protein binding | 88.2% |
| Metabolism | CYP3A4 |
| Eliminationhalf-life | 20–25 hrs |
| Excretion | Mainly feces |
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| IUPHAR/BPS | |
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| ChEBI | |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.041.188 |
| Chemical and physical data | |
| Formula | C18H14Cl4N2O |
| Molar mass | 416.12 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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Miconazole, sold under the brand nameMonistat among others, is anantifungal medication used to treatring worm,pityriasis versicolor, andyeast infections of the skin or vagina.[2] It is used for ring worm of thebody,groin (jock itch), andfeet (athlete's foot).[2] It is applied to the skin or vagina as a cream or ointment.[2][3]
Common side effects include itchiness or irritation of the area in which it was applied.[2] Use inpregnancy is believed to be safe for the baby.[4] Miconazole is in theimidazole family of medications.[2] It works by decreasing the ability of fungi to makeergosterol, an important part of theircell membrane.[2]
Miconazole was patented in 1968 and approved for medical use in 1971.[5] It is on theWorld Health Organization's List of Essential Medicines.[6] It is available as ageneric medication.[2]
Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot.[2] Internal application is used fororal candidiasis orvaginal thrush (yeast infection).[2]
Miconazole is generally well tolerated. The oral gel can cause dry mouth,nausea and an unpleasant taste in about 1–10% of people.Anaphylactic reactions are rare. The drug prolongs theQT interval.[7][8]
Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally.[9] This can lead to increased concentrations of drugs that are metabolized by the liver enzymesCYP3A4 andCYP2C9, because miconazole inhibits these enzymes. Such interactions occur for example withanticoagulants of thewarfarin type,phenytoin, some neweratypical antipsychotics,ciclosporin, and moststatins used to treathypercholesterolemia.[8] These interactions are not relevant for miconazole that is applied to the skin.[8]
Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:[8]
Miconazole inhibits the fungal enzyme14α-sterol demethylase, resulting in a reduced production of ergosterol.[10] In addition to its antifungal actions, miconazole, similarly toketoconazole, is known to act as anantagonist of theglucocorticoid receptor.[11] Miconazole is also known to bind totubulin and inhibit its polymerization.[12]
After application to the skin, miconazole can be measured in the skin for up to four days, but less than 1% is absorbed into the bloodstream. When applied to theoral mucosa (and possibly also for vaginal use[9]), it is significantly absorbed. In the bloodstream, 88.2% are bound toplasma proteins and 10.6% toblood cells. The substance is partlymetabolized via the liver enzyme CYP3A4 and mainly eliminated via the faeces.[7][8]
The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.[13] Miconazole crystallises as colourless prisms in themonoclinic space group P21/c.[14]
Miconazole is also used inEktachrome film developing in the final rinse of theKodakE-6 process and similar Fuji CR-56 process,[citation needed] replacingformaldehyde.[15][16]Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.[citation needed]
Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):[citation needed]
In 2010, the US Food and Drug Administration approved Oravig (miconazole) buccal tablets for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older.[1]
External skin treatment (brand names Desenex and Zeasorb in US and Canada; Micatin, Monistat-Derm, Daktarin in India, UK, Australia, Belgium and the Philippines; Kalpanax in Indonesia; Daktar in Norway; Fungidal in Bangladesh; Decocort in Malaysia)[citation needed] (Note that Desenex originally contained not miconazole, but rather the fungistatic agents,undecylenic acid and zinc undecylenate, which were in the foot powder developed by the US government for troops during WWII.[17])
Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):[citation needed]
In Japan, Mochida Healthcare, a subsidiary ofMochida Pharmaceutical, produces a line of body soaps and shampoo under the brand name Collage (コラージュ) that contain miconazole nitrate as their main ingredient.[18]
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