MICONAZOLE

US Approved OTC

First approved in 1974

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H14Cl4N2O
Molecular Weight	416.129
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(cc(c1COC(Cn2ccnc2)c3ccc(cc3Cl)Cl)Cl)Cl

InChI

InChIKey=BYBLEWFAAKGYCD-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H14Cl4N2O
Molecular Weight	416.129
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1149649 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf | http://www.antimicrobe.org/drugpopup/Miconazole.pdf

Miconazole is a synthetic imidazole derivative, a topical antifungal agent for use in the local treatment of vaginal, and skin and nail infections due to yeasts and dermatophytes. It is particularly active against Candida spp., Trichophyton spp., Epidermophyton spp., Microsporum spp. and Pityrosporon orbiculare (Malassezia furfur), but also possesses some activity against Gram-positive bacteria. It binds to the heme moiety of the fungal cytochrome P-450 dependent enzyme lanosterol 14-alpha-demethlyase. Inhibits 14-alpha-demethlyase, blocks formation of ergosterol and leads to the buildup of toxic methylated 14-a-sterols. Miconazole also affects the synthesis of triglycerides and fatty acids and inhibits oxidative and peroxidative enzymes, increasing the amount of active oxygen species within the cell.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 20 Target ID: CHEMBL1780 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Inhibitor 3315
Sphingosine-1-phosphate lyase 1 2 Target ID: CHEMBL3286061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28930429	Inhibitor 3315

Conditions

Condition	Modality	Highest Phase	Product
Oropharyngeal candidiasis 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Curative	Approved 4033	ORAVIG Approved Use ORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults Launch Date 1.26144004E11
Vulvovaginal candidiasis 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21308s009lbl.pdf	Curative	Approved 4033	MONISTAT 1 COMBINATION PACK Approved Use Used to treats vaginal yeast infections, relieves external itching and irritation due to a vaginal yeast infection Launch Date 9.9368639E11
Multiple sclerosis 44 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25896324	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
39.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		MICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
136.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		MICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		MICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1200 mg single, vaginal Recommended Dose: 1200 mg Route: vaginal Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/	unhealthy, 18 - 60 years n = 50 Health Status: unhealthy Condition: vaginal candidosis Age Group: 18 - 60 years Sex: F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/	Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/
200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B itraconazole Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	Disc. AE: Fibrillation ventricular... AEs leading to discontinuation/dose reduction: Fibrillation ventricular (grade 5, 11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B itraconazole Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	Disc. AE: Bradyarrhythmia... AEs leading to discontinuation/dose reduction: Bradyarrhythmia (5.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
0.25 % 7 times / day steady, topical Recommended Dose: 0.25 %, 7 times / day Route: topical Route: steady Dose: 0.25 %, 7 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16570675/	unhealthy, newborns n = 330 Health Status: unhealthy Condition: Diaper dermatitis complicated by candidiasis Age Group: newborns Sex: M+F Population Size: 330 Sources: https://pubmed.ncbi.nlm.nih.gov/16570675/	Sources: https://pubmed.ncbi.nlm.nih.gov/16570675/

AEs

AE	Significance	Dose	Population
Fibrillation ventricular	grade 5, 11.1% Disc. AE	200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B itraconazole Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
Bradyarrhythmia	5.2% Disc. AE	800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B itraconazole Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 753	inhibitor 825	inhibitor 894	inhibitor 775

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 725 CYP2A6 334 CYP2B6 371 CYP2C19 700 CYP2E1 424 CYP3A4/5 122	P-gp 724

Drug as perpetrator

Target	Modality	Activity
CYP3A4 920	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [IC50 0.175 uM]
CYP2C19 738	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.01 uM]
CYP3A4/5 142	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.028 uM]
CYP2B6 465	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.05 uM]
CYP2D6 908	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.7 uM]
CYP2C9 851	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 1.2 uM]
CYP2A6 356	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 2.2 uM]
CYP1A2 805	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 3.2 uM]
CYP2E1 467	inhibitor 1612 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 7.3 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 724	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 796	inhibitor 786 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1576066/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY542733	https://www.001chemical.com/chem/22832-87-7
001 Chemical	NO20569	https://www.001chemical.com/chem/22916-47-8
3B Scientific (Wuhan) Corp	3B3-027676	http://www.3bsc.com/index/pro_info.php?id=48932
AA Blocks	AA002LEB	http://www.aablocks.com/goods/Goods/detail?id=AA002LEB
AEchem Scientific Corp., USA	AE1-012982	http://www.aechemsc.com/info_products/AE1-012982.php
AHH Chemical co.,ltd	MT-08479	http://www.ahhchemical.com/product/MT-08479.html
AK Scientific, Inc. (AKSCI)	J10390	http://www.aksci.com/item_detail.php?cat=J10390
AK Scientific, Inc. (AKSCI)	W4662	http://www.aksci.com/item_detail.php?cat=W4662
Aaron Chemicals	AR002M63	http://www.aaronchem.com/22916-47-8
AbMole Bioscience	M5787	http://www.abmole.com/products/miconazole.html
Achemo Scientific Limited	AC-76854	http://www.achemo.com/search/?Keyword= 22916-47-8
Achemtek	0104-034719	http://www.achemtek.com/22916-47-8
Acorn PharmaTech	ACN-041287	http://www.acornpharmatech.com/
Alfa Chemistry	AP22916478	https://reagents.alfa-chemistry.com/product/miconazole-cas-22916-47-8-8228.html
Angene	AGN-PC-0QZHGM	http://www.angenechemical.com/productshow/AGN-PC-0QZHGM.html
Anward	ANW-42336	http://www.anward.com/pro_result/26251
Ark Pharm	AK-34234	http://www.arkpharminc.com/products/22916-47-8.html
AstaTech, Inc.	35147	http://www.astatechinc.com/CPSResult.php?CRNO=35948
Aurum Pharmatech LLC	M-4631	http://www.Aurumpharmatech.com/Product/ProductDetails/M_4631
Avantor Inc	101095-560	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-560
BLD Pharm	BD55353	http://www.bldpharm.com/products/22916-47-8.html
BioSynth	J-014898	https://www.biosynth.com/en/products/all-products/products/J-014898.html
CSNpharm	CSN17106	https://www.csnpharm.com/products/miconazole.html
Chem Scene	CS-2565	http://www.chemscene.com/22916-47-8.html
ChemMol	44001698	http://www.chemmol.com/chemmol/44001698.html
ChemMol	99051027	http://www.chemmol.com/chemmol/99051027.html
Chemspace	CSSB00000062152	https://chem-space.com/CSSB00000062152
Clearsynth	CS-O-01866	https://www.clearsynth.com/en/CSO01866.html
Debye Scientific	DB-046018	http://www.debyesci.com/cas_22916-47-8.html
Finetech	FT-0628942	http://www.finetechnology-ind.com/prod/detail/pub/22916-47-8.html
Glentham Life Sciences	GA8311	http://www.glentham.com/products/product/GA8311/
Hairui	HR135292	http://www.hairuichem.com/en/product/22832-87-7.html
Hairui	HR124240	http://www.hairuichem.com/en/product/22916-47-8.html
LGC Standards	DRE-C15260090	https://www.lgcstandards.com/US/en/p/DRE-C15260090
LGC Standards	LGCFOR0074.00	https://www.lgcstandards.com/US/en/p/LGCFOR0074.00
LGC Standards	MM0074.00	https://www.lgcstandards.com/US/en/p/MM0074.00
Lab Network	LN00188719	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188719
Matrix Scientific	90792	https://www.matrixscientific.com/090792.html
MedChem Express	HY-B0454	https://www.medchemexpress.com/miconazole.html
Molcore	MC542733	https://www.molcore.com/product/22832-87-7
Molcore	CS20569	https://www.molcore.com/product/22916-47-8
OChem	4276	http://www.ocheminc.com/index.php?act=psearch&pid=216M019
Oakwood	361942	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=150806&ExtHyperLink=1
Parchem	29423	http://www.parchem.com/chemical-supplier-distributor/Miconazole-019423.aspx
Parchem	31848	http://www.parchem.com/chemical-supplier-distributor/Miconazole-Base-021848.aspx
Smolecule	S535407	http://www.smolecule.com/products/s535407
THE BioTek	bt-276215	https://www.thebiotek.com/product/inhibitors/bt-276215
THE BioTek	bt-298613	https://www.thebiotek.com/product/others/bt-298613
abcr GmbH	AB349199	http://www.abcr.com/shop/en/AB349199
eNovation Chemicals	D155603	http://www.enovationchem.com/productDetails.asp?productID=D155603
eNovation Chemicals	D674548	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674548
eNovation Chemicals	D787472	https://www.enovationchem.com/ProductDetails.asp?ProductID=D787472
iChemical	EBD21177	http://www.ichemical.com/products/22916-47-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-2106181573	https://mcule.com/MCULE-2106181573/

PubMed

Title	Date	PubMed
In vitro synergism between nyasol, an active compound isolated from Anemarrhena asphodeloides, and azole agents against Candida albicans.	2000 Jun	10909263
Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis.	2000 Nov 15	11064188
In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens.	2000 Oct	11132964
Systemic Candida infection in University hospital 1997-1999: the distribution of Candida biotypes and antifungal susceptibility patterns.	2001	11307597
[Current problems in etiotropic therapy of mycoses].	2001	11221084
Spectrophotometric resolution of metronidazole and miconazole nitrate in ovules using ratio spectra derivative spectrophotometry and RP-LC.	2001 Apr	11274865
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.	2001 Apr 17	11306529
The importance of reassessment to chronic wound care.	2001 Aug	11889999
Suppression of transient outward potassium currents in mouse ventricular myocytes by imidazole antimycotics and by glybenclamide.	2001 Aug	11454921
Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis.	2001 Aug 28	11522375
Reduced glutathione, dithiothreitol and cytochrome P-450 inhibitors do not influence hypoxic chemosensory responses in the rat carotid body.	2001 Jan 19	11166696
Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report.	2001 Jul	12024935
Systemic antifungal agents.	2001 Jul	11519290
Characterization of endothelium-derived hyperpolarizing factor in the human forearm microcirculation.	2001 Jun	11356600
Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation.	2001 Jun	11356598
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.	2001 Jun 15	11377375
Influence of the roll compactor parameter settings and the compression pressure on the buccal bio-adhesive tablet properties.	2001 Jun 4	11376975
A novel bovine lactoferrin peptide, FKCRRWQWRM, suppresses Candida cell growth and activates neutrophils.	2001 Mar	11298926
Progestins block cholesterol synthesis to produce meiosis-activating sterols.	2001 Mar	11259396
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions.	2001 May 15	11339818
Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats.	2001 Nov	11668072
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.	2001 Oct	11744942
Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.	2001 Oct	11598232
Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart.	2001 Oct	11588519
Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles.	2001 Sep	11675950
The role of endothelium-derived hyperpolarizing factor in the regulation of the uterine circulation in pregnant rats.	2001 Sep	11568792
Reversal effects of antifungal drugs on multidrug resistance in MDR1-overexpressing HeLa cells.	2001 Sep	11558564
Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis.	2002 Apr	11914502
N-methyl-D-aspartate-induced vasodilation is mediated by endothelium-independent nitric oxide release in piglets.	2002 Apr	11893577
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.	2002 Feb	11834610
Fungal keratitis caused by Scedosporium apiospermum: report of two cases and review of treatment.	2002 Jul	12072730
Severe keratomycosis secondary to Scedosporium apiospermum.	2002 Jul	12072729
7-Benzyloxyquinoline oxidation by P450eryF A245T: finding of a new fluorescent substrate probe.	2002 Jun	12067248
Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials.	2002 Jun 15	12115356
Inhibition of cytochromes P450 by antifungal imidazole derivatives.	2002 Mar	11854151
Enhancement of skin permeation of miconazole by phospholipid and dodecyl 2-(N,N-dimethyl amino)propionate (DDAIP).	2002 Mar 2	11839443
[A case of abrupt pulmonary infection by Rhizopus microsporus var. rhizopodiformis during treatment for bronchial asthma].	2002 May	12073577

Patents

Sample Use Guides

In Vivo Use Guide

Application of one ORAVIG 50 mg buccal tablet to the gum region once daily for 14 consecutive days. External miconazole nitrate vulvar cream (2%): twice daily, for up to 7 days as needed. Miconazole nitrate vaginal insert (1200mg): with the applicator place the vaginal insert into the vagina.

Route of Administration: Other

In Vitro Use Guide

The antifungal drug, miconazole nitrate, inhibits the growth of several species of Candida. Candida albicans, one of the pathogenic species, was totally inhibited at a concentration of approximately 10 mug/ml.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:52:46 UTC 2021` Edited by `admin` on `Fri Jun 25 20:52:46 UTC 2021`
Record UNII	7NNO0D7S5M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MICONAZOLE

Official Name

English

MICONAZOLE [EP]

Common Name

English

(+/-)-1-(2,4-DICHLORO-B-((2,4-DICHLOROBENZYL)OXY)PHENETHYL)IMIDAZOLE

Common Name

English

MICONAZOLE [JAN]

Common Name

English

MICONAZOLE [USP]

Common Name

English

MICONAZOLE [VANDF]

Common Name

English

MICONAZOLE [WHO-DD]

Common Name

English

1H-IMIDAZOLE, 1-2-((2,4-DICHLOROPHENYL)-2-((2,4-DICHLOROPHENYL))METHOXY)ETHYL)-, (+/-)-

Common Name

English

MICONAZOLE [INN]

Common Name

English

MICONAZOLE [MART.]

Common Name

English

MICONAZOLE [USP MONOGRAPH]

Common Name

English

MICONAZOLE [ORANGE BOOK]

Common Name

English

MICONAZOLE [EP MONOGRAPH]

Common Name

English

MICONAZOLE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD01AC02