Miconazole

Miconazole

Systematic (IUPAC) name
(RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
Clinical data
Trade names	Monistat
AHFS/Drugs.com	monograph
MedlinePlus	a601203
Pregnancy cat.	?
Legal status	POM (UK) OTC (US)
Routes	topical, vaginal
Pharmacokinetic data
Bioavailability	n/a
Metabolism	n/a
Half-life	n/a
Excretion	n/a
Identifiers
CAS number	22916-47-8 Y
ATC code	D01AC02 A01AB09 A07AC01 G01AF04
PubChem	CID 4189
IUPHAR ligand	2449
DrugBank	APRD01115
ChemSpider	4044 Y
UNII	7NNO0D7S5M Y
KEGG	D00416 Y
ChEBI	CHEBI:6923 N
ChEMBL	CHEMBL91 Y
Chemical data
Formula	C18H14Cl4N2O
Mol. mass	416.127 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucus 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 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 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.

Indications

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). In addition the oral gel may also be used for the lip disorder angular cheilitis.

It has an advantage over nystatin 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^[1]) which may lead to drug interactions.

Of note may be interactions 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:

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.^[2]

See also

• Antifungal drugs
• Castor oil
• Clotrimazole
• Cremophor EL
• E-6 process
• Ektachrome
• Isoconazole

References

1. ^ British National Formulary '45' March 2003
2. ^ United States Patent 5461068

External links

Medical

• Micatin
• Miconazole (www.meds-help.com)
• 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)