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

ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

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 28 Target ID: CHEMBL1780 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Inhibitor 8146
Sphingosine-1-phosphate lyase 1 4 Target ID: CHEMBL3286061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28930429	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Oropharyngeal candidiasis 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Curative	Approved 8307	ORAVIG Approved Use ORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults Launch Date 1.26144004E11
Vulvovaginal candidiasis 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21308s009lbl.pdf	Curative	Approved 8307	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 101 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 1532	inhibitor 1695	inhibitor 1789	inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1463 CYP2A6 670 CYP2B6 770 CYP2C19 1410 CYP2E1 846 CYP3A4/5 261	P-gp 1491

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1857	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [IC50 0.175 uM]
CYP2C19 1484	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.01 uM]
CYP3A4/5 314	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.028 uM]
CYP2B6 946	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.05 uM]
CYP2D6 1826	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.7 uM]
CYP2C9 1747	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 1.2 uM]
CYP2A6 702	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 2.2 uM]
CYP1A2 1620	inhibitor 3185 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 3.2 uM]
CYP2E1 929	inhibitor 3185 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 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1603	inhibitor 1584 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
Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp.	2000 Jun	11810544
[Klion D - possibilities of prophylaxis and treatment during pregnancy].	2001	11803871
The importance of reassessment to chronic wound care.	2001 Aug	11889999
[Infection and colonization by Scedosporium prolificans].	2001 Aug-Sep	11747789
Anti-mycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis.	2001 Dec	11886533
Effect of estrogen on flow-induced dilation in NO deficiency: role of prostaglandins and EDHF.	2001 Dec	11717219
Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report.	2001 Jul	12024935
Effects of azoles on human acute myelogenous leukemia blasts and T lymphocytes derived from acute leukemia patients with chemotherapy-induced cytopenia.	2001 Nov	11710547
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.	2001 Nov	11682448
Initial and sustained phases of myogenic response of rat mesenteric small arteries.	2001 Nov	11668080
Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats.	2001 Nov	11668072
Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates.	2001 Oct	11760221
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.	2001 Oct	11744942
Androgen metabolism in oyster Crassostrea gigas: evidence for 17beta-HSD activities and characterization of an aromatase-like activity inhibited by pharmacological compounds and a marine pollutant.	2001 Oct	11717006
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
[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use].	2001 Oct-Dec	11833253
Candida keratitis in a patient with candidiasis of the fingernails.	2001 Oct-Dec	11820312
Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles.	2001 Sep	11675950
Distribution and susceptibility of Candida species isolated in the Medical University of Debrecen.	2002	12109169
Routine versus selective antifungal administration for control of fungal infections in patients with cancer.	2002	12076377
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
Antitumor effects of miconazole on human colon carcinoma xenografts in nude mice through induction of apoptosis and G0/G1 cell cycle arrest.	2002 Apr 1	11922774
[Efficacy and tolerance of 200 mg of fenticonazole versus 400 mg of miconazole in the intravaginal treatment of mycotic vulvovaginitis].	2002 Feb	12017948
Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076.	2002 Feb	12002999
Use of cisapride with contraindicated drugs in The Netherlands.	2002 Feb	11847959
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.	2002 Feb	11834610
Sex-specific acute effect of estrogen on endothelium-derived contracting factor in the renal artery of hypertensive Dahl rats.	2002 Feb	11821708
Role of endothelium in hyperemia during cortical spreading depression (CSD) in the rat.	2002 Feb 22	11844470
Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults.	2002 Jan	11808824
Lontophoresis for the treatment of paecilomyces keratitis.	2002 Jan	11805526
Comparative study of the enantiomeric resolution of chiral antifungal drugs econazole, miconazole and sulconazole by HPLC on various cellulose chiral columns in normal phase mode.	2002 Jan 15	11755745
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
Inhibition of sarcoplasmic reticulum Ca2+-ATPase by miconazole.	2002 Jul	12055076
Interaction between warfarin and topical miconazole cream.	2002 Jul 13	12114237
The opposite effects of cyclic AMP-protein kinase a signal transduction pathway on renal cortical and medullary Na+,K+-ATPase activity.	2002 Jun	12120897
Overanticoagulation associated with combined use of antifungal agents and coumarin anticoagulants.	2002 Jun	12087353
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
Rapid viability assessment of yeast cells using vital staining with 2-NBDG, a fluorescent derivative of glucose.	2002 Jun 5	12038577
Effect of direct infusion of antifungal agent on invasive pulmonary aspergillosis in a patient with acute leukemia.	2002 Mar	11957130
Comparison of dermatopharmacokinetic vs. clinicial efficacy methods for bioequivalence assessment of miconazole nitrate vaginal cream, 2% in humans.	2002 Mar	11934233
Effect of antifungal azoles on the heme detoxification system of malarial parasite.	2002 Mar	11872173
Inhibition of cytochromes P450 by antifungal imidazole derivatives.	2002 Mar	11854151
ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators.	2002 Mar 15	11870854
Enhancement of skin permeation of miconazole by phospholipid and dodecyl 2-(N,N-dimethyl amino)propionate (DDAIP).	2002 Mar 2	11839443
Pityriasis versicolor rubra.	2002 Mar-Apr	11872414
[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 Dec 16 16:23:07 UTC 2022` Edited by `admin` on `Fri Dec 16 16:23:07 UTC 2022`
Record UNII	7NNO0D7S5M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MICONAZOLE

Official Name

English

Miconazole [WHO-DD]

Common Name

English

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

Common Name

English

MICONAZOLE [JAN]

Common Name

English

MICONAZOLE [VANDF]

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 [USP IMPURITY]

Common Name

English

MICONAZOLE [MART.]

Common Name

English

MICONAZOLE [USP MONOGRAPH]

Common Name

English

MICONAZOLE [EP IMPURITY]

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