Miconazole

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Miconazole
Miconazole2DCSD.svg
Miconazole ball-and-stick.png
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 cat.
  • AU: A
  • US: C
  • In Australia, it is category A when used topically. In the US, the pregnancy category is C for oral and topical treatment.
Legal status
Routes topical, vaginal
Pharmacokinetic data
Bioavailability n/a
Metabolism n/a
Half-life n/a
Excretion n/a
Identifiers
CAS number 22916-47-8 YesY
ATC code A01AB09 A07AC01 D01AC02 G01AF04 J02AB01 S02AA13
PubChem CID 4189
IUPHAR ligand 2449
DrugBank DB01110
ChemSpider 4044 YesY
UNII 7NNO0D7S5M YesY
KEGG D00416 YesY
ChEBI CHEBI:6923 YesY
ChEMBL CHEMBL91 YesY
Chemical data
Formula C18H14Cl4N2O 
Mol. mass 416.127 g/mol
 YesY (what is this?)  (verify)

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.[1]

Medical uses[edit]

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[edit]

Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally[2]); this may lead to drug interactions.

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

Brand names and formulations[edit]

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.[citation needed]

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[edit]

Miconazole has recently gained some popularity as a hair-growth aid,[3] although little evidence indicates its efficacy. Topical application of ketoconazole, a similar drug, has been shown to increase hair growth.[4] However, oral administration of ketoconazole has also been shown to reduce hair growth in cases of hirsutism.[5]

Physical properties[edit]

The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.[6]

See also[edit]

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ British National Formulary '45' March 2003
  3. ^ "Strange Beauty: Monistat Effectively Increases Hair Growth?". Black Girl With Long Hair. Retrieved 12 April 2012. 
  4. ^ Ju, Jiang; Tsuboi, Ryoji; Kojima, Yuko; Ogawa, Hideoki (2005). "Topical application of ketoconazole stimulates hair growth in C3H/HeN mice". Journal of dermatology 32: 243–247. 
  5. ^ S., Venturoli; O. Marescalchi, F. M. Colombo, S. Macrelli, B. Ravaioli, A. Bagnoli, R. Paradisi and C. Flamigni (April 1999). "A Prospective Randomized Trial Comparing Low Dose Flutamide, Finasteride, Ketoconazole, and Cyproterone Acetate-Estrogen Regimens in the Treatment of Hirsutism". The Journal of Clinical Endocrinology and Metabolism 84 (4): 1304–1310. doi:10.1210/jc.84.4.1304. Retrieved 12 April 2012. 
  6. ^ United States Patent 5461068

External links[edit]

Medical[edit]

Photographic[edit]