Miconazole

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| _other_data=(RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

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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.<ref name=AHFS2016/> It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot).<ref name=AHFS2016/> It is applied to the skin or vagina as a cream or ointment.<ref name=AHFS2016>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Common side effects include itchiness or irritation of the area in which it was applied.<ref name=AHFS2016/> Use in pregnancy is believed to be safe for the baby.<ref name=Ric2015>Template:Cite book</ref> Miconazole is in the imidazole family of medications.<ref name=AHFS2016/> It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane.<ref name=AHFS2016/>

Miconazole was patented in 1968 and approved for medical use in 1971.<ref name=Fis2006>Template:Cite book</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO23rd">Template:Cite book</ref> It is available as a generic medication.<ref name=AHFS2016/>

Medical uses

Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot.<ref name=AHFS2016/> Internal application is used for oral candidiasis or vaginal thrush (yeast infection).<ref name=AHFS2016/>

Side effects

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 the QT interval.<ref name="AC" /><ref name="AC-gel" />

Interactions

Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally.<ref name="BNF">British National Formulary '45' March 2003</ref> This can lead to increased concentrations of drugs that are metabolized by the liver enzymes CYP3A4 and CYP2C9, because miconazole inhibits these enzymes. Such interactions occur for example with anticoagulants of the warfarin type, phenytoin, some newer atypical antipsychotics, ciclosporin, and most statins used to treat hypercholesterolemia.<ref name="AC-gel" /> These interactions are not relevant for miconazole that is applied to the skin.<ref name="AC-gel" />

Contraindications

Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:<ref name="AC-gel" />

• drugs that also prolong the QT interval because of potential problems with the heart rhythm
• ergot alkaloids
• statins
• triazolam and oral midazolam
• sulfonamides with a potential to cause hypoglycaemia (low blood sugar)

Pharmacology

Mechanism of action

Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol.<ref>Template:Cite journal</ref> In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.<ref name="pmid16608920">Template:Cite journal</ref>

Pharmacokinetics

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 the oral mucosa (and possibly also for vaginal use<ref name="BNF" />), it is significantly absorbed. In the bloodstream, 88.2% are bound to plasma proteins and 10.6% to blood cells. The substance is partly metabolized via the liver enzyme CYP3A4 and mainly eliminated via the faeces.<ref name="AC">Template:Cite book</ref><ref name="AC-gel">Template:Cite book</ref>

Chemistry

The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.<ref>Template:Cite patent</ref> Miconazole crystallises as colourless prisms in the monoclinic space group P2₁/c.<ref>Template:Cite journal</ref>

Other uses

Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process,Template:Citation needed replacing formaldehyde.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.Template:Citation needed

Brands and formulations

File:Miconazol.jpg

Vaginal miconazole 20 mg/g - Brazil

Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):Template: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.<ref name="Oravig FDA label" />

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)Template: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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>)

Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):Template:Citation needed

In Japan, Mochida Healthcare, a subsidiary of Mochida 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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>