Miconazole

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.[1] It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot).[1] It is applied to the skin or vagina as a cream or ointment.[1]

Miconazole
Clinical data
Trade namesDesenex, Monistat, others
AHFS/Drugs.comMonograph
MedlinePlusa601203
Pregnancy
category
  • AU: A (when used topically)
  • US: C (Risk not ruled out) (for topical use)
    Routes of
    administration
    Topical, vaginal, sublabial
    ATC code
    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
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.041.188
    Chemical and physical data
    FormulaC18H14Cl4N2O
    Molar mass416.127 g·mol−1
    3D model (JSmol)
    ChiralityRacemic mixture
      (verify)

    Common side effects include itchiness or irritation of the area in which it was applied.[1] Use in pregnancy is believed to be safe for the baby.[2] Miconazole is in the imidazole family of medications.[1] It works by decreasing the ability of fungi to make ergosterol, an important part of its cell membrane.[1]

    Miconazole was patented in 1968 and approved for medical use in 1971.[3] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[4] The wholesale cost in the developing world is about 0.23 to US$0.60 for a 30 gram tube.[5] In the United States a course of treatment costs less than US$25.[2]

    Medical uses

    Miconazole is mainly used externally for the treatment of ringworm including jock itch and athlete's foot. Internal application is used for oral or vaginal thrush (yeast infection). This oral gel may also be used for the lip disorder angular cheilitis and other associated systems.

    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[6]); 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.

    Pharmacology

    Pharmacodynamics

    Miconazole inhibits the fungal enzyme 14α-sterol demethylase, which reduces production of ergosterol.[7] In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.[8]

    Chemistry

    The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.[9]

    Other uses

    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.

    Brands and formulations

    Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):

    • 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 (brand names 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: 2-5%
    • 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 (brand names 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

    References

    1. "Miconazole Nitrate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
    2. Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560.
    3. Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495. Archived from the original on 2016-12-20.
    4. "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
    5. "Miconazole Nitrate". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 8 December 2016.
    6. British National Formulary '45' March 2003
    7. Becher, R; Wirsel, SG (August 2012). "Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens". Applied Microbiology and Biotechnology. 95 (4): 825–40. doi:10.1007/s00253-012-4195-9. PMID 22684327.
    8. 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.
    9. United States Patent 5461068 Archived 2014-09-10 at the Wayback Machine
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