Miconazole

Miconazole
Clinical data
Trade namesMonistat, others
AHFS/Drugs.comMonograph
MedlinePlusa601203
License data
Routes of
administration		Topical, vaginal, sublabial
ATC code
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[citation needed]
  • UK: POM (Prescription only)
  • US: OTC / Rx-only[1]
Pharmacokinetic data
Bioavailability<1% after application to the skin
Protein binding88.2%
MetabolismCYP3A4
Elimination half-life20–25 hrs
ExcretionMainly feces
Identifiers
  • (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.188 Edit this at Wikidata
Chemical and physical data
FormulaC18H14Cl4N2O
Molar mass416.12 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.[2] It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot).[2] It is applied to the skin or vagina as a cream or ointment.[2][3]

Common side effects include itchiness or irritation of the area in which it was applied.[2] Use in pregnancy is believed to be safe for the baby.[4] Miconazole is in the imidazole family of medications.[2] It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane.[2]

Miconazole was patented in 1968 and approved for medical use in 1971.[5] It is on the World Health Organization's List of Essential Medicines.[6] It is available as a generic medication.[2]

  1. ^ "Oravig- miconazole tablet". DailyMed. 1 January 2022. Archived from the original on 14 August 2022. Retrieved 20 June 2023.
  2. ^ a b c d e f g "Miconazole Nitrate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  3. ^ "Miconazole Monograph for Professionals". Drugs.com. 22 July 2022. Archived from the original on 21 September 2022. Retrieved 20 June 2023.
  4. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495. Archived from the original on 20 December 2016.
  6. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.