Miconazole

Miconazole
Clinical data
Trade names	Monistat, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601203
License data	US DailyMed: Miconazole;
Routes of; administration	Topical, vaginal, sublabial
ATC code	A01AB09 (WHO) A07AC01 (WHO) D01AC02 (WHO) G01AF04 (WHO) J02AB01 (WHO) S02AA13 (WHO);
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 / Rx-only;
Pharmacokinetic data
Bioavailability	<1% after application to the skin
Protein binding	88.2%
Metabolism	CYP3A4
Elimination half-life	20–25 hrs
Excretion	Mainly feces
Identifiers
	IUPAC name (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole;
CAS Number	22916-47-8 ;
PubChem CID	4189;
IUPHAR/BPS	2449;
DrugBank	DB01110 ;
ChemSpider	4044 ;
UNII	7NNO0D7S5M;
KEGG	D00416 ;
ChEBI	CHEBI:6923 ;
ChEMBL	ChEMBL91 ;
CompTox Dashboard (EPA)	DTXSID6023319 ;
ECHA InfoCard	100.041.188
Chemical and physical data
Formula	C18H14Cl4N2O
Molar mass	416.12 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl;
	InChI 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 ; Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N ;
	(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]

^ "Oravig- miconazole tablet". DailyMed. 1 January 2022. Archived from the original on 14 August 2022. Retrieved 20 June 2023.
^ ^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.
^ "Miconazole Monograph for Professionals". Drugs.com. 22 July 2022. Archived from the original on 21 September 2022. Retrieved 20 June 2023.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495. Archived from the original on 20 December 2016.
^ 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.

[Oravig_FDA_label-1] "Oravig- miconazole tablet". DailyMed. 1 January 2022. Archived from the original on 14 August 2022. Retrieved 20 June 2023.

[AHFS2016-2] ^ ^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.

[Ric2015-4] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560.

[Fis2006-5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495. Archived from the original on 20 December 2016.

[WHO23rd-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.

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