Mr. Ibrahem/Miconazole
Clinical data
Trade namesDesenex, Monistat, others
AHFS/Drugs.comMonograph
MedlinePlusa601203
Pregnancy
category
  • AU: A(when used topically)
Routes of
administration
Topical, vaginal, sublabial
Drug classAntifungal medication (imidazole)[1]
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) Schedule 2 for topical formulations, schedule 3 for vaginal use and for oral candidiasis, otherwise schedule 4
  • UK: POM (Prescription only)
  • US: OTC
Pharmacokinetic data
Bioavailability<1% after topical application
Protein binding88.2%
ExcretionMainly faeces
Identifiers
  • (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
Chemical and physical data
FormulaC18H14Cl4N2O
Molar mass416.127 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl
  • 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 checkY
  • Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N checkY
  (verify)

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]

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.[5] Miconazole is in the imidazole family of medications.[1] It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane.[1]

Miconazole was patented in 1968 and approved for medical use in 1971.[6] It is on the World Health Organization's List of Essential Medicines.[7] The wholesale cost in the developing world is about US$0.23 to US$0.60 for a 30 gram tube.[8] In the United States a course of treatment costs less than US$25.[5]

References

edit
  1. ^ a b c d e f g h i "Miconazole Nitrate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  2. ^ Cite error: The named reference WHO2020DDDO was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference WHO2020DDDI was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference WHO2020DDDV was invoked but never defined (see the help page).
  5. ^ a b Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560.
  6. ^ 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.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ "Miconazole Nitrate". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 8 December 2016.