Miconazole
Encyclopedia
Miconazole is an imidazole
Imidazole
Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and is classified as an alkaloid. Imidazole refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying substituents...

 antifungal agent, developed by Janssen Pharmaceutica
Janssen Pharmaceutica
Janssen Pharmaceutica is pharmaceutical company, established in Belgium in 1953 by Paul Janssen. Its headquarters are located in Beerse, in the Campine region of the province of Antwerp, Belgium. It was created not as a subsidiary of a chemical factory but solely with the aim of conducting...

, commonly applied topically to the skin
Skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...

 or to mucus membranes to cure fungal infection
Mycosis
A mycosis is a fungal infection of animals, including humans. Mycoses are common, and a variety of environmental and physiological conditions can contribute to the development of fungal diseases...

s. It works by inhibiting the synthesis of ergosterol
Ergosterol
Ergosterol is a sterol found in fungi, and named for ergot, a common name for the members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells...

, a critical component of fungal cell membrane
Cell membrane
The cell membrane or plasma membrane is a biological membrane that separates the interior of all cells from the outside environment. The cell membrane is selectively permeable to ions and organic molecules and controls the movement of substances in and out of cells. It basically protects the cell...

s. It can also be used against certain species of Leishmania
Leishmania
Leishmania is a genus of Trypanosomatid protozoa, and is the parasite responsible for the disease leishmaniasis. It is spread through sandflies of the genus Phlebotomus in the Old World, and of the genus Lutzomyia in the New World. Their primary hosts are vertebrates; Leishmania commonly infects...

protozoa
Protozoa
Protozoa are a diverse group of single-cells eukaryotic organisms, many of which are motile. Throughout history, protozoa have been defined as single-cell protists with animal-like behavior, e.g., movement...

 which are a type of unicellular parasite that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some limited antibacterial properties. It is marketed in various formulations under various brand names.

Miconazole is also used in Ektachrome
Ektachrome
Ektachrome is a brand name owned by Kodak for a range of transparency, still, and motion picture films available in most formats, including 35 mm and sheet sizes to 11x14 inch size. Ektachrome has a distinctive look that became familiar to many readers of National Geographic, which used it...

 film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

. Fuji Hunt
Fujifilm
is a multinational photography and imaging company headquartered in Tokyo, Japan.Fujifilm's principal activities are the development, production, sale and servicing of color photographic film, digital cameras, photofinishing equipment, color paper, photofinishing chemicals, medical imaging...

 also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.

Indications

Miconazole is mainly used externally for the treatment of athlete's foot
Athlete's foot
Athlete's foot is a fungal infection of the skin that causes scaling, flaking, and itch of affected areas. It is caused by fungi in the genus Trichophyton and is typically transmitted in moist areas where people walk barefoot, such as showers or bathhouses...

, ringworm and jock itch
Jock itch
Tinea cruris, also known as crotch itch, crotch rot, Dhobie itch, eczema marginatum, gym itch, jock itch, and ringworm of the groin in American English is a dermatophyte fungal infection of the groin region in either sex, though more often seen in males...

. Internal application is used for oral or vaginal thrush (yeast infection). In addition the oral gel may also be used for the lip disorder angular cheilitis
Angular cheilitis
Angular cheilitis is an inflammatory lesion at the labial commissure, or corner of the mouth, and often occurs bilaterally. The condition manifests as deep cracks or splits...

.

It has an advantage over nystatin
Nystatin
Nystatin is a polyene antifungal medication to which many molds and yeast infections are sensitive, including Candida. Due to its toxicity profile, there are currently no injectable formulations of this drug on the US market...

 in the treatment of neonatal oral thrush in that the latter is only licensed in the UK for those over the age of one month; but note the possibility for drug interactions.

Side effects

Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally) - which may lead to drug interactions.

Note possible interactions with anticoagulant
Anticoagulant
An anticoagulant is a substance that prevents coagulation of blood. A group of pharmaceuticals called anticoagulants can be used in vivo as a medication for thrombotic disorders. Some anticoagulants are used in medical equipment, such as test tubes, blood transfusion bags, and renal dialysis...

s, phenytoin
Phenytoin
Phenytoin sodium is a commonly used antiepileptic. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels...

, terbinafine
Terbinafine
Terbinafine hydrochloride is a...

, some newer atypical antipsychotics, ciclosporin
Ciclosporin
Ciclosporin , cyclosporine , cyclosporin , or cyclosporin A is an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the immune system, and therefore the risk of organ rejection...

 and some statin
Statin
Statins are a class of drugs used to lower cholesterol levels by inhibiting the enzyme HMG-CoA reductase, which plays a central role in the production of cholesterol in the liver. Increased cholesterol levels have been associated with cardiovascular diseases, and statins are therefore used in the...

s used to treat hypercholesterolemia
Hypercholesterolemia
Hypercholesterolemia is the presence of high levels of cholesterol in the blood. It is not a disease but a metabolic derangement that can be caused by many diseases, notably cardiovascular disease...

.

Brand names and formulations

Oral treatment: (brands: Daktarin in UK)
  • Oral gel 24 mg/ml (20 mg/g)


  • Oravig 50 mg once daily buccal tablet:


On April 16, 2010 the U.S. Food and Drug Administration approved Oravig (miconazole) buccal tablets once daily for the local treatment of oropharyngeal candidiasis (OPC), more commonly known as thrush, in adults and children age 16 and older. Oravig is the first and only local, oral prescription formulation of miconazole - an antifungal medication - approved for this use in the U.S.

External skin treatment: (brands: Desenex in US and Canada (not to be confused with Tussionex), Micatin, Monistat-Derm, Daktarin in UK, Australia, Belgium and the Philippines, Decocort in Malaysia)
  • Topical cream: 2%.
  • Combination: 2% cream with 1% hydrocortisone (Daktacort in UK, Daktodor in Greece)


Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktarin in UK)
  • Pessaries: 200 mg or 100 mg
  • Vaginal cream: 2% (7-day treatment); 4% (3-day treatment)
  • Combination: 2% cream with either 100 mg or 200 mg.

Physical properties

The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.

See also

  • Antifungal medication
  • Castor oil
    Castor oil
    Castor oil is a vegetable oil obtained from the castor bean . Castor oil is a colorless to very pale yellow liquid with mild or no odor or taste. Its boiling point is and its density is 961 kg/m3...

  • Clotrimazole
    Clotrimazole
    Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections such as vaginal yeast infections, oral thrush, and ringworm...

  • Cremophor EL
    Cremophor EL
    Cremophor EL is the registered trademark of BASF Corp. for its version of polyethoxylated castor oil. It is prepared by reacting 35 moles of ethylene oxide with each mole of castor oil...

  • E-6 process
    E-6 process
    The E-6 process is a chromogenic photographic process for developing Ektachrome, Fujichrome and other color reversal photographic film....

  • Ektachrome
    Ektachrome
    Ektachrome is a brand name owned by Kodak for a range of transparency, still, and motion picture films available in most formats, including 35 mm and sheet sizes to 11x14 inch size. Ektachrome has a distinctive look that became familiar to many readers of National Geographic, which used it...

  • Isoconazole
    Isoconazole
    Isoconazole is an azole antifungal drug. Nigerian and British medical researchers found that for foot and vaginal infections, isoconazole has a similar effectiveness to clotrimazole....


Medical


Photographic

  • Kodak process E6 Ektachrome
    Ektachrome
    Ektachrome is a brand name owned by Kodak for a range of transparency, still, and motion picture films available in most formats, including 35 mm and sheet sizes to 11x14 inch size. Ektachrome has a distinctive look that became familiar to many readers of National Geographic, which used it...

    (color transparency) processing manual Z-119
  • Kodak process E6 Q-LAB processing manual Z-6 (more details than processing manual Z119 above)
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