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.
Routes of
administration		 topical, vaginal, sublabial, oral
Legal status
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
Pharmacokinetic data
Bioavailability n/a
Metabolism n/a
Biological half-life n/a
Excretion n/a
Identifiers
CAS Number 22916-47-8 YesY
ATC code A01AB09 (WHO) A07AC01 D01AC02 G01AF04 J02AB01 S02AA13
PubChem CID 4189
IUPHAR/BPS 2449
DrugBank DB01110 YesY
ChemSpider 4044 YesY
UNII 7NNO0D7S5M YesY
KEGG D00416 YesY
ChEBI CHEBI:6923 YesY
ChEMBL CHEMBL91 YesY
Chemical data
Formula C18H14Cl4N2O
Molar mass 416.127 g/mol
Chirality Racemic mixture
  (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

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[2]); this may lead to drug interactions.

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

Brand names and formulations

Vaginal miconazole 20 mg/g - Brazil

Oral treatment: (brands: Daktarin in UK)

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)

Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktarin in UK)

Off-label use

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]

Pharmacology

In addition to its antifungal actions, miconazole, along with ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.[6]

Remyelination

Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models.[7]

Physical properties

The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.[8]

See also

References

  1. ↑ "WHO Model List of EssentialMedicines" (PDF). 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; 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. ↑ Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, Vilarem MJ, Maurel P, Gerbal-Chaloin S (2006). "Ketoconazole and miconazole are antagonists of the human glucocorticoid receptor: consequences on the expression and function of the constitutive androstane receptor and the pregnane X receptor". Mol. Pharmacol. 70 (1): 329–39. doi:10.1124/mol.105.022046. PMID 16608920.
  7. ↑ Najm, Fadi J.; Madhavan, Mayur; Zaremba, Anita; Shick, Elizabeth; Karl, Robert T.; Factor, Daniel C.; Miller, Tyler E.; Nevin, Zachary S.; Kantor, Christopher (2015-01-01). "Drug-based modulation of endogenous stem cells promotes functional remyelination in vivo". Nature 522 (7555). doi:10.1038/nature14335.
  8. ↑ United States Patent 5461068

External links

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