Miconazole

Miconazole

Clinical data
Trade names	Desenex, Monistat, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601203
Pregnancy category	AU: A (when used topically) US: C (for topical use)
Routes of administration	topical, vaginal, sublabial
ATC code	A01AB09 (WHO) A07AC01 (WHO) D01AC02 (WHO) G01AF04 (WHO) J02AB01 (WHO) S02AA13 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) Schedule 2 for topical formulations, schedule 3 for vaginal use and for oral candidiasis, otherwise schedule 4 UK: POM (Prescription only) US: OTC
Identifiers
IUPAC name (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
CAS Number	22916-47-8 Y
PubChem CID	4189
IUPHAR/BPS	2449
DrugBank	DB01110 Y
ChemSpider	4044 Y
UNII	7NNO0D7S5M
KEGG	D00416 Y
ChEBI	CHEBI:6923 Y
ChEMBL	CHEMBL91 Y
ECHA InfoCard	100.041.188
Chemical and physical data
Formula	C18H14Cl4N2O
Molar mass	416.127 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl
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

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 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 its 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.23 to 0.60 USD for a 30 gm tube. In the United States a course of treatment costs less than 25 USD.

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.