Miconazole

Miconazole

Systematic (IUPAC) name
(RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
Clinical data
Trade names	Desenex, Monistat, Zeasorb-AF
AHFS/Drugs.com	monograph
MedlinePlus	a601203
Pregnancy category	AU: A US: C (Risk not ruled out) In Australia, it is category A when used topically. In the US, the pregnancy category is C for oral and topical treatment.
Legal status	AU: S2 (Pharmacy only) UK: POM (Prescription only) US: OTC Schedule 2 in Australia for topical formulations, schedule 3 (Aus) for vaginal use and for oral candidiasis, otherwise schedule 4 in Australia
Routes of administration	topical, vaginal, sublabial, oral
Pharmacokinetic data
Bioavailability	n/a
Metabolism	n/a
Biological half-life	n/a
Excretion	n/a
Identifiers
CAS Number	22916-47-8 Y
ATC code	A01AB09 (WHO) A07AC01 D01AC02 G01AF04 J02AB01 S02AA13
PubChem	CID: 4189
IUPHAR/BPS	2449
DrugBank	DB01110 Y
ChemSpider	4044 Y
UNII	7NNO0D7S5M Y
KEGG	D00416 Y
ChEBI	CHEBI:6923 Y
ChEMBL	CHEMBL91 Y
Chemical data
Formula	C18H14Cl4N2O
Molecular mass	416.127 g/mol
SMILES Clc1ccc(c(Cl)c1)C(OCc2ccc(Cl)cc2Cl)Cn3ccnc3
InChI InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2 Y Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N Y
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Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucous membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa which are a type of unicellular parasites that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some antibacterial properties. It is marketed in various formulations under various brand names.

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.

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.

Medical uses

Miconazole is mainly used externally for the treatment of athlete's foot, ringworm, and jock itch. Internal application is used for oral or vaginal thrush (yeast infection). The oral gel may also be used for the lip disorder angular cheilitis.

In the UK, miconazole may be used to treat neonatal oral thrush, while the alternative nystatin is only licensed for patients over the age of one month, but drug interactions are possible.

Side effects

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

Interactions are possible with anticoagulants, phenytoin, terbinafine,, some newer atypical antipsychotics, ciclosporin, and some statins used to treat hypercholesterolemia.

Brand names and formulations

Vaginal miconazole 20 mg/g - Brazil

Oral treatment: (brands: Daktarin in UK)

• 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: (brands: 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%
• 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: (brands: 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

Off-label use

Miconazole has recently gained some popularity as a hair-growth aid, although little evidence indicates its efficacy. Topical application of ketoconazole, a similar drug, has been shown to increase hair growth. However, oral administration of ketoconazole has also been shown to reduce hair growth in cases of hirsutism.

Pharmacology

In addition to its antifungal actions, miconazole, along with ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.

Remyelination

Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models.

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
• Clotrimazole
• Cremophor EL
• Isoconazole

External links

Medical

• Micatin
• Miconazole (National Institutes of Health)
• United States Patent 5461068 Imidazole derivative tincture and method of manufacture

Photographic

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