Miconazole: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Drugbox
			{{Use dmy dates\|date=September 2024}}
	\| Verifiedfields = changed
			{{cs1 config \|name-list-style=vanc \|display-authors=6}}
	\| verifiedrevid = 411361909
			{{Infobox drug
	\| IUPAC_name = (''RS'')-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1''H''-imidazole
			\| Watchedfields = changed
	\| image = Miconazole structure.png
			\| verifiedrevid = 461740624
	\| width = 200px
			\| image = Miconazole.svg
	\| imagename = 1 : 1 mixture (racemate)
			\| image_class = skin-invert-image
	\| drug_name = Miconazole
			\| width = 200
			\| alt =
			\| image2 = Miconazole ball-and-stick.png
			\| image_class2 = bg-transparent
			\| width2 = 200
			\| alt2 =
			\| chirality = ]

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename = Monistat		\| tradename = Monistat, others
	\| Drugs.com = {{drugs.com\|monograph\|miconazole~~-nitrate~~}}		\| Drugs.com = {{drugs.com\|monograph\|miconazole}}
	\| MedlinePlus = a601203		\| MedlinePlus = a601203
			\| DailyMedID = Miconazole
	\| pregnancy_category =
			\| pregnancy_AU =
			\| pregnancy_AU_comment =
			\| pregnancy_category =
			\| routes_of_administration = ], ], ]
			\| ATC_prefix = A01
			\| ATC_suffix = AB09
			\| ATC_supplemental = {{ATC\|A07\|AC01}} {{ATC\|D01\|AC02}} {{ATC\|G01\|AF04}} {{ATC\|J02\|AB01}} {{ATC\|S02\|AA13}}

			\| legal_AU = S2
			\| legal_AU_comment = Schedule 2 for topical formulations, schedule 3 for vaginal use and for oral ], otherwise schedule 4{{citation needed\|date=June 2023}}
			\| legal_CA =
	\| legal_UK = POM		\| legal_UK = POM
	\| legal_US = OTC		\| legal_US = OTC
			\| legal_US_comment = / Rx-only<ref name="Oravig FDA label">{{cite web \| title=Oravig- miconazole tablet \| website=DailyMed \| date=1 January 2022 \| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dc2427ff-e566-4b48-b289-9e51c011250a \| access-date=20 June 2023 \| archive-date=14 August 2022 \| archive-url=https://web.archive.org/web/20220814225102/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dc2427ff-e566-4b48-b289-9e51c011250a \| url-status=live }}</ref>
	\| legal_status =
	\| routes_of_administration = ], ]

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| bioavailability = ~~n/a~~		\| bioavailability = <1% after application to the skin
	\| ~~metabolism~~ = ~~n/a~~		\| protein_bound = 88.2%
			\| metabolism = ]
	\| elimination_half-life = n/a
			\| elimination_half-life = 20–25 hrs
	\| excretion = n/a
			\| excretion = Mainly feces

	<!--Identifiers-->		<!--Identifiers-->
	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 22916-47-8		\| CAS_number = 22916-47-8
	\| ATC_prefix = D01
	\| ATC_suffix = AC02
	\| ATC_supplemental = {{ATC\|A01\|AB09}} {{ATC\|A07\|AC01}} {{ATC\|G01\|AF04}}
	\| PubChem = 4189		\| PubChem = 4189
	\| IUPHAR_ligand = 2449		\| IUPHAR_ligand = 2449
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = ~~APRD01115~~		\| DrugBank = DB01110
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 4044		\| ChemSpiderID = 4044
Line 41:		Line 55:
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D00416		\| KEGG = D00416
	\| ChEBI_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 6923		\| ChEBI = 6923
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 91		\| ChEMBL = 91
			\| synonyms =

	<!--Chemical data-->		<!--Chemical data-->
			\| IUPAC_name = (''RS'')-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1''H''-imidazole
	\| C=18 \| H=14 \| Cl=4 \| N=2 \| O=1
			\| C=18 \| H=14 \| Cl=4 \| N=2 \| O=1
	\| molecular_weight = 416.127 g/mol
	\| ~~smiles~~ = ~~Clc1ccc(c~~(Cl)c1)~~C(OCc2ccc~~(Cl)~~cc2Cl)Cn3ccnc3~~		\| SMILES = Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl
	\| InChI = 1/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
	\| InChIKey = BYBLEWFAAKGYCD-UHFFFAOYAA
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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		\| StdInChI = 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
Line 58:		Line 71:
	}}		}}

			<!-- Definition and medical uses -->
	'''Miconazole''' is an ] ] agent, developed by ], commonly applied topically to the ] or to ] to cure ] infections. It works by inhibiting the synthesis of ], a critical component of fungal ]s. It can also be used against certain species of '']'' ] which are a type of unicellular ] that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some limited ] properties. It is marketed in various formulations under various brand names.
			'''Miconazole''', sold under the brand name '''Monistat''' among others, is an ] used to treat ], ], and ] of the skin or vagina.<ref name=AHFS2016/> It is used for ring worm of the ], ] (jock itch), and ] (athlete's foot).<ref name=AHFS2016/> It is applied to the skin or vagina as a cream or ointment.<ref name=AHFS2016>{{cite web\|title=Miconazole Nitrate\|url=https://www.drugs.com/monograph/miconazole-nitrate.html\|publisher=The American Society of Health-System Pharmacists\|access-date=8 December 2016\|url-status=live\|archive-url=https://web.archive.org/web/20161221013013/https://www.drugs.com/monograph/miconazole-nitrate.html\|archive-date=21 December 2016}}</ref><ref>{{cite web \| title=Miconazole Monograph for Professionals \| website=Drugs.com \| date=22 July 2022 \| url=https://www.drugs.com/monograph/miconazole.html \| access-date=20 June 2023 \| archive-date=21 September 2022 \| archive-url=https://web.archive.org/web/20220921191831/https://www.drugs.com/monograph/miconazole.html \| url-status=live }}</ref>

			<!-- Side effects and mechanism -->
	Miconazole is also used in ] film developing in the final rinse of the ] E-6 process and similar Fuji CR-56 process, replacing ]. ] also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.
			Common side effects include itchiness or irritation of the area in which it was applied.<ref name=AHFS2016/> Use in ] is believed to be safe for the baby.<ref name=Ric2015>{{cite book\| vauthors = Hamilton R \|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition \|date=2015 \|publisher=Jones & Bartlett Learning \|isbn=9781284057560 \|page=180 }}</ref> Miconazole is in the ] family of medications.<ref name=AHFS2016/> It works by decreasing the ability of fungi to make ], an important part of their ].<ref name=AHFS2016/>

			<!-- History and culture -->
	==Indications==
			Miconazole was patented in 1968 and approved for medical use in 1971.<ref name=Fis2006>{{cite book\| vauthors = Fischer J, Ganellin CR \|title=Analogue-based Drug Discovery\|date=2006\|publisher=John Wiley & Sons\|isbn=9783527607495\|page=502\|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA502\|url-status=live\|archive-url=https://web.archive.org/web/20161220144314/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA502\|archive-date=2016-12-20}}</ref> It is on the ].<ref name="WHO23rd">{{cite book \| vauthors = ((World Health Organization)) \| title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) \| year = 2023 \| hdl = 10665/371090 \| author-link = World Health Organization \| publisher = World Health Organization \| location = Geneva \| id = WHO/MHP/HPS/EML/2023.02 \| hdl-access=free }}</ref> It is available as a ].<ref name=AHFS2016/>
	Miconazole is mainly used externally for the treatment of ], ] and ]. Internal application is used for ] or ] ] (]). In addition the oral gel may also be used for the lip disorder ].


			==Medical uses==
	It has an advantage over ] in the treatment of ] oral thrush in that the latter is only licensed in the UK for those over the age of one month; but note the possibility for drug interactions.
			Miconazole is used externally for the treatment of ], ], and ].<ref name=AHFS2016/> Internal application is used for ] or ] (]).<ref name=AHFS2016/>

	==Side effects==		==Side effects==
			Miconazole is generally well tolerated. The oral gel can cause dry mouth, ] and an unpleasant taste in about 1–10% of people. ]s are rare. The drug prolongs the ].<ref name="AC" /><ref name="AC-gel" />
	Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally<ref>] '45' March 2003</ref>) which may lead to drug interactions.

			== Interactions ==
	Of note may be interactions with ]s, ], ], some newer ], ] and some ]s used to treat ].
			Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally.<ref name="BNF">] '45' March 2003</ref> This can lead to increased concentrations of drugs that are metabolized by the liver enzymes ] and ], because miconazole inhibits these enzymes. Such interactions occur for example with ]s of the ] type, ], some newer ]s, ], and most ]s used to treat ].<ref name="AC-gel" /> These interactions are not relevant for miconazole that is applied to the skin.<ref name="AC-gel" />

			==Contraindications==
	==Brand names and formulations==
			Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:<ref name="AC-gel" />
			* drugs that also prolong the QT interval because of potential problems with the heart rhythm
			* ]s
			* statins
			* ] and oral ]
			* ]s with a potential to cause ] (low blood sugar)

			==Pharmacology==
	]
			===Mechanism of action===
	Oral treatment: (brands: Daktarin in UK)
			Miconazole inhibits the fungal enzyme ], resulting in a reduced production of ergosterol.<ref>{{cite journal \| vauthors = Becher R, Wirsel SG \| title = Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens \| journal = Applied Microbiology and Biotechnology \| volume = 95 \| issue = 4 \| pages = 825–840 \| date = August 2012 \| pmid = 22684327 \| doi = 10.1007/s00253-012-4195-9 \| s2cid = 17688962 }}</ref> In addition to its antifungal actions, miconazole, similarly to ], is known to act as an ] of the ].<ref name="pmid16608920">{{cite journal \| vauthors = Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, Vilarem MJ, Maurel P, Gerbal-Chaloin S \| display-authors = 6 \| title = 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 \| journal = Molecular Pharmacology \| volume = 70 \| issue = 1 \| pages = 329–339 \| date = July 2006 \| pmid = 16608920 \| doi = 10.1124/mol.105.022046 \| s2cid = 21455699 }}</ref>
	*Oral gel 24 mg/ml (20 mg/g)

			===Pharmacokinetics===
	'''
			After application to the skin, miconazole can be measured in the skin for up to four days, but less than 1% is absorbed into the bloodstream. When applied to the ] (and possibly also for vaginal use<ref name="BNF" />), it is significantly absorbed. In the bloodstream, 88.2% are bound to ]s and 10.6% to ]s. The substance is partly ] via the liver enzyme CYP3A4 and mainly eliminated via the faeces.<ref name="AC">{{cite book\|title=Austria-Codex\| veditors = Haberfeld H \|at=Daktarin 2%-Creme\|publisher=Österreichischer Apothekerverlag\|location=Vienna\|year=2019\|language=de}}</ref><ref name="AC-gel">{{cite book\|title=Austria-Codex\| veditors = Haberfeld H \|at=Daktarin 2%-orales Gel\|publisher=Österreichischer Apothekerverlag\|location=Vienna\|year=2020\|language=de}}</ref>
	* Oravig 50 mg once daily buccal tablet:

	On April 16, 2010 the U.S. Food and Drug Administration approved Oravig (miconazole) buccal tablets once daily for the local treatment of oropharyngeal candidiasis (OPC), more commonly known as thrush, in adults and children age 16 and older. Oravig is the first and only local, oral prescription formulation of miconazole - an antifungal medication - approved for this use in the U.S.

			==Chemistry==
	External skin treatment: (brands: ] in US and Canada (not to be confused with Tussionex), ], Monistat-Derm, Daktarin in UK, Australia, Belgium and the Philippines, Decocort in Malaysia)
			The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.<ref>{{cite patent \| inventor = Thaler I, Strauss R \| country = US \| number = 5461068 \| title = Imidazole derivative tincture and method of manufacture \| assign1 = Current Assignee Corwood Laboratories Inc \| assign2 = Bausch Health Companies Inc \| gdate = 24 October 1995 \| postscript = . }}</ref> Miconazole crystallises as colourless prisms in the ] space group P2<sub>1</sub>/c.<ref>{{cite journal \| vauthors = Kaspiaruk H, Chęcińska L \| title = A comparison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate \| journal = Acta Crystallographica Section C \| volume = 78 \| issue = Pt 6 \| pages = 343–350 \| date = June 2022 \| pmid = 35662134 \| doi = 10.1107/S2053229622004909 \| s2cid = 248839249 }}</ref>
	*Topical cream: 2%.
	*Combination: 2% cream with 1% ] (Daktacort in UK, Daktodor in Greece)

			==Other uses==
	Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktarin in UK)
			Miconazole is also used in ] film developing in the final rinse of the ] ] and similar Fuji CR-56 process,{{citation needed\|date=June 2023}} replacing ].<ref>{{cite web \| title=Kodak Chemicals: Process E-6 Publication: Z-119 \| website=Kodak \| date=8 October 1999 \| url=http://www.kodak.com/global/en/service/Zmanuals/z119.shtml \| archive-url=https://web.archive.org/web/20070715005022/http://www.kodak.com/global/en/service/Zmanuals/z119.shtml \| archive-date=15 July 2007 \| url-status=dead \| access-date=20 June 2023}}</ref><ref>{{cite web \| title=Kodak Chemicals: Q-LAB Process Control Handbook: Publication Z-6 \| website=Kodak \| date=1 November 2004 \| url=http://www.kodak.com/global/en/service/Zmanuals/z6.shtml \| archive-url=https://web.archive.org/web/20070207080023/http://www.kodak.com/global/en/service/Zmanuals/z6.shtml \| archive-date=7 February 2007 \| url-status=dead \| access-date=20 June 2023}}</ref> ] also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.{{citation needed\|date=December 2022}}
	*Pessaries: 200 mg or 100 mg
	*Vaginal cream: 2% (7-day treatment); 4% (3-day treatment)
	*Combination: 2% cream with either 100 mg or 200 mg.

			==Brands and formulations==
	==Physical properties==
			]
	The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.<ref></ref>

			Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):{{citation needed\|date=December 2022}}
	==See also==
	* ]s
	* ]
	* ]
	* ]
	* ]
	* ]
	* ]

			In 2010, the US Food and Drug Administration approved Oravig (miconazole) buccal tablets for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older.<ref name="Oravig FDA label" />
	==References==
	{{reflist}}

			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){{citation needed\|date=December 2022}} (Note that Desenex originally contained not miconazole, but rather the fungistatic agents, ] and zinc undecylenate, which were in the foot powder developed by the US government for troops during WWII.<ref>{{Cite web \|title=History \|url=https://achh.army.mil/history/book-wwii-communicablediseasesv5-chapter7/ \|access-date=2024-03-03 \|website=achh.army.mil \|language=en \|archive-date=2024-03-03 \|archive-url=https://web.archive.org/web/20240303214812/https://achh.army.mil/history/book-wwii-communicablediseasesv5-chapter7/ \|url-status=live }}</ref>)
	==External links==
	===Medical===
	*
	* (www.meds-help.com)
	* (National Institutes of Health)
	* Imidazole derivative tincture and method of manufacture

			Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):{{citation needed\|date=December 2022}}
	===Photographic===
			{{clear}}
	* ] (color transparency) processing manual Z-119

	* processing manual Z-6 (more details than processing manual Z119 above)
			In Japan, Mochida Healthcare, a subsidiary of ], produces a line of body soaps and shampoo under the brand name Collage (コラージュ) that contain miconazole nitrate as their main ingredient.<ref>{{Cite web\|title=Mochida Pharmaceutical Co., list of product ingredients\|url=https://hc.mochida.co.jp/products/ingredients/list.html\|access-date=2024-08-21\|website=hc.mochida.co.jp\|language=ja}}</ref>

			== References ==
			{{reflist}}

	{{Stomatological preparations}}		{{Stomatological preparations}}
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	{{Gynecological anti-infectives and antiseptics}}		{{Gynecological anti-infectives and antiseptics}}
	{{Otologicals}}		{{Otologicals}}
			{{Glucocorticoid receptor modulators}}
			{{Portal bar \| Medicine}}
			{{Authority control}}

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Latest revision as of 16:03, 12 January 2025

Chemical compound

Pharmaceutical compound

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

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

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

Medical uses

Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot. Internal application is used for oral candidiasis or vaginal thrush (yeast infection).

Side effects

Miconazole is generally well tolerated. The oral gel can cause dry mouth, nausea and an unpleasant taste in about 1–10% of people. Anaphylactic reactions are rare. The drug prolongs the QT interval.

Interactions

Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally. This can lead to increased concentrations of drugs that are metabolized by the liver enzymes CYP3A4 and CYP2C9, because miconazole inhibits these enzymes. Such interactions occur for example with anticoagulants of the warfarin type, phenytoin, some newer atypical antipsychotics, ciclosporin, and most statins used to treat hypercholesterolemia. These interactions are not relevant for miconazole that is applied to the skin.

Contraindications

Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:

drugs that also prolong the QT interval because of potential problems with the heart rhythm
ergot alkaloids
statins
triazolam and oral midazolam
sulfonamides with a potential to cause hypoglycaemia (low blood sugar)

Pharmacology

Mechanism of action

Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol. In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.

Pharmacokinetics

After application to the skin, miconazole can be measured in the skin for up to four days, but less than 1% is absorbed into the bloodstream. When applied to the oral mucosa (and possibly also for vaginal use), it is significantly absorbed. In the bloodstream, 88.2% are bound to plasma proteins and 10.6% to blood cells. The substance is partly metabolized via the liver enzyme CYP3A4 and mainly eliminated via the faeces.

Chemistry

The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid. Miconazole crystallises as colourless prisms in the monoclinic space group P2₁/c.

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):

In 2010, the US Food and Drug Administration approved Oravig (miconazole) buccal tablets for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older.

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) (Note that Desenex originally contained not miconazole, but rather the fungistatic agents, undecylenic acid and zinc undecylenate, which were in the foot powder developed by the US government for troops during WWII.)

Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):

In Japan, Mochida Healthcare, a subsidiary of Mochida Pharmaceutical, produces a line of body soaps and shampoo under the brand name Collage (コラージュ) that contain miconazole nitrate as their main ingredient.

References

^ "Oravig- miconazole tablet". DailyMed. 1 January 2022. Archived from the original on 14 August 2022. Retrieved 20 June 2023.
^ "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.
^ Haberfeld H, ed. (2019). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Daktarin 2%-Creme.
^ Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Daktarin 2%-orales Gel.
^ British National Formulary '45' March 2003
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): 825–840. doi:10.1007/s00253-012-4195-9. PMID 22684327. S2CID 17688962.
Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, et al. (July 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". Molecular Pharmacology. 70 (1): 329–339. doi:10.1124/mol.105.022046. PMID 16608920. S2CID 21455699.{{cite journal}}: CS1 maint: overridden setting (link)
US 5461068, Thaler I, Strauss R, "Imidazole derivative tincture and method of manufacture", issued 24 October 1995, assigned to Current Assignee Corwood Laboratories Inc and Bausch Health Companies Inc.
Kaspiaruk H, Chęcińska L (June 2022). "A comparison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate". Acta Crystallographica Section C. 78 (Pt 6): 343–350. doi:10.1107/S2053229622004909. PMID 35662134. S2CID 248839249.
"Kodak Chemicals: Process E-6 Publication: Z-119". Kodak. 8 October 1999. Archived from the original on 15 July 2007. Retrieved 20 June 2023.
"Kodak Chemicals: Q-LAB Process Control Handbook: Publication Z-6". Kodak. 1 November 2004. Archived from the original on 7 February 2007. Retrieved 20 June 2023.
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v t e Stomatological preparations (A01)
Caries prophylaxis	Dectaflur Olaflur Sodium fluoride Sodium monofluorophosphate Stannous fluoride
Infection and antiseptics	Amphotericin B Benzoxonium chloride Chlorhexidine Chlortetracycline Clotrimazole Cetylpyridinium chloride Domiphen bromide Doxycycline Eugenol Hexetidine Hydrogen peroxide Mepartricin Metronidazole Miconazole Minocycline Natamycin Neomycin Oxyquinoline Polynoxylin Sodium perborate Tetracycline Tibezonium iodide
Corticosteroids (Glucocorticoids)	Dexamethasone Hydrocortisone Triamcinolone
Other	Amlexanox Acetylsalicylic acid Becaplermin Benzydamine Epinephrine/Adrenalone

v t e Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (+atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone Hydrocortisone Prednisone Betamethasone Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
WHO-EM Withdrawn from market Clinical trials: Phase III Never to phase III

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles

Systemic: ketoconazole

Triazoles

Unknown: albaconazole
ravuconazole

Thiazoles

Topical: abafungin

Polyene antimycotics
(ergosterol binding)

Topical: hamycin
natamycin
nystatin
Systemic: amphotericin B, hamycin

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	Systemic: flucytosine
Mitotic inhibitors	Systemic: griseofulvin
Aminoacyl tRNA synthetase inhibitors	Topical: tavaborole

Others

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole
Triazoles	Terconazole
Polyenes	Nystatin Natamycin Amphotericin B
Other	Ciclopirox Methylrosaniline

Other

v t e Drugs used for diseases of the ear (S02)
Infection	Acetic acid Aluminium acetotartrate Aluminium triacetate (Burow's solution) Boric acid Chloramphenicol Chlorhexidine Ciprofloxacin Clioquinol Gentamicin Hydrogen peroxide Miconazole Neomycin Nitrofurazone Ofloxacin Polymyxin B Rifamycin Tetracycline
Corticosteroids	Betamethasone Dexamethasone Fluocinolone acetonide Hydrocortisone Prednisolone
Analgesics and anesthetics	Lidocaine Cocaine Phenazone

Glucocorticoid receptor modulators

GRTooltip Glucocorticoid receptor

Agonists	Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 9α-Fluorocortisone (alfluorone) 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) 11-Dehydrocorticosterone acetate 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone) Desoxycortone esters 11-Deoxycortisol (cortodoxone, cortexolone) Cortifen (cortiphen, kortifen) Cortodoxone acetate 21-Deoxycortisol Δ-Prednisolone Δ-Prednisolone 21-acetate Amebucort Chloroprednisone Chloroprednisone acetate Cloprednol Cloprednol acetate Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol (hydrocortisone) Benzodrocortisone (hydrocortisone benzoate) Hydrocortamate (hydrocortisone diethylaminoacetate) Hydrocortisone esters Cortisone Cortisone acetate Deprodone Deprodone propionate Dichlorisone Dichlorisone acetate Dichlorisone diacetate Difluprednate Endrisone (endrysone) Etiprednol Etiprednol dicloacetate (etiprednol dichloroacetate) Fludrocortisone (fludrocortone) Fludrocortisone acetate Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Halopredone Halopredone acetate (halopredone diacetate) Isoflupredone (9α-fluoroprednisolone) Isoflupredone acetate Loteprednol Mazipredone (depersolone) Medrysone Methylprednisolone Methylprednisolone esters Prebediolone Prebediolone acetate Prednisolone Prednazate Prednazoline Prednicarbate (prednisolone ethylcarbonate propionate) Prednimustine Prednisolamate (prednisolone diethylaminoacetate) Prednisolone esters Prednisone Prednisone esters Pregnenolone Pregnenolone acetate Pregnenolone succinate (pregnenolone hemisuccinate) Resocortol Tipredane Tixocortol Butixocort (tixocortol butyrate) Butixocort propionate Tixocortol pivalate Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone Alclometasone Alclometasone dipropionate Amelometasone Beclometasone (beclomethasone) Beclometasone esters Betamethasone (betametasone) Betamethasone esters Cortobenzolone (betamethasone salicylate) Ciclometasone (ciclomethasone, cyclomethasone) Clobetasol Clobetasol propionate Clobetasone Clobetasone butyrate Clocortolone Clocortolone esters Cloticasone Cloticasone propionate Cormetasone (cormethasone) Cormetasone acetate Descinolone Desoximetasone (desoxymethasone) Dexamethasone (dexametasone) Dexamethasone esters Diflorasone Diflorasone diacetate Diflucortolone Diflucortolone pivalate Diflucortolone valerate Dimesone Dimesone acetate Doxibetasol (doxybetasol) Fluclorolone Flumetasone (flumethasone) Flumetasone acetate Flumetasone pivalate Fluocinolone Fluocortin Fluocortin butyl (fluocortin butylate) Fluocortolone Fluocortolone esters Fluprednidene (fluprednylidene) Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halocortolone Halometasone Icometasone Icometasone enbutate (icometasone butyrate acetate) Isoprednidene Locicortolone (locicortone) Locicortolone dicibate (locicortone dicibate) Meclorisone Meclorisone dibutyrate Meprednisone (methylprednisone) Meprednisone acetate Meprednisone hydrogen succinate (methylprednisone hemisuccinate) Mometasone Mometasone furoate Paramethasone Paramethasone acetate Paramethasone disodium phosphate Paramethasone phosphate Prednylidene Prednylidene diethylaminoacetate Rimexolone Ticabesone Ticabesone propionate Timobesone Timobesone acetate Triamcinolone Triamcinolone diacetate Ulobetasol (halobetasol) Ulobetasol propionate Vamorolone Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide) Amcinafal (triamcinolone pentanonide) Amcinafide (triamcinolone acetophenide) Amcinonide (triamcinolone acetate cyclopentanonide) Budesonide Ciclesonide Cicortonide Deflazacort (azacort) Descinolone acetonide Desonide (hydroxyprednisolone acetonide) Desonide disodium phosphate Desonide pivalate Dexbudesonide Drocinonide Drocinonide phosphate Fluazacort Fluclorolone acetonide (flucloronide) Fludroxycortide (flurandrenolone, flurandrenolide) Flumoxonide Flunisolide Flunisolide acetate Fluocinolone acetonide Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate) Fluocinonide (fluocinolide, fluocinolone acetonide acetate) Procinonide (fluocinolone acetonide propionate) Formocortal Halcinonide Itrocinonide Rofleponide Rofleponide palmitate Tralonide Triamcinolone acetonide Flupamesone (triamcinolone acetonide metembonate) Triamcinolone acetonide esters Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB) Triclonide Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol Cortivazol Domoprednate Naflocort Nicocortonide Nicocortonide acetate Nivacortol (nivazol) Oxisopred RU-26988 RU-28362 Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone Bromoketoprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Danazol Delmadinone acetate Desogestrel DU-41165 Etonogestrel Flugestone Flugestone acetate (flurogestone acetate) Fluoromedroxyprogesterone acetate Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone RU-2309 Quingestrone Segesterone acetate (nestorone) Tetrahydrogestrinone Nonsteroidal glucocorticoids: AZD-5423 GSK-9027
Mixed (SEGRMsTooltip Selective glucocorticoid receptor agonists)	Dagrocorat Fosdagrocorat Mapracorat
Antagonists	7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT-108297 Cyproterone acetate Dazucorilant Exicorilant (CORT-125281) Guggulsterone Ketoconazole Lilopristone LLY-2707 Metapristone (RU-42633) Miconazole Mifepristone (RU-486) Miricorilant (CORT-118335) Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Relacorilant (CORT-125134) RTI 3021–012 RTI 3021–022 Telapristone Tibolone Toripristone Ulipristal acetate Zavacorilant
Others	Antisense oligonucleotides: IONIS-GCCR_Rx (ISIS-426115)

See also: Receptor/signaling modulators; Glucocorticoids and antiglucocorticoids; Mineralocorticoid receptor modulators; List of corticosteroids

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