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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
MedlinePlus
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
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 Registry Number  Y
ATC code A01 A07 D01 G01 J02 S02
PubChem CID:
IUPHAR/BPS
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C18H14Cl4N2O
Molecular mass 416.127 g/mol
 Y   

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 health system.[1]

Contents

  • Medical uses 1
  • Side effects 2
  • Brand names and formulations 3
  • Off-label use 4
  • Pharmacology 5
  • Remyelination 6
  • Physical properties 7
  • See also 8
  • References 9
  • External links 10
    • Medical 10.1
    • Photographic 10.2

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, 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,[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.  
  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.  
  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).  
  8. ^ United States Patent 5461068

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)
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