ECONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H15Cl3N2O
Molecular Weight	381.684
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(COC(CN2C=CN=C2)C3=CC=C(Cl)C=C3Cl)C=C1

InChI

InChIKey=LEZWWPYKPKIXLL-UHFFFAOYSA-N

InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2

HIDE SMILES / InChI

Molecular Formula	C18H15Cl3N2O
Molecular Weight	381.684
Charge	0
Count

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/98315

Econazole (commonly used as the nitrate salt) is an antifungal medication of the imidazole class. It is a broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. Sold under the brand name Ecoza among others, it is indicated for the treatment of interdigital tinea pedis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum in patients 12 years of age and older. Econazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.drugbank.ca/drugs/DB01127 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/20149798	Inhibitor 8504		17.9 nM [Kd]
Trichophyton rubrum 5 Target ID: CHEMBL612649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2737705 \| https://www.ncbi.nlm.nih.gov/pubmed/400880	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tinea pedis 28 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=121446	Curative		Approved 8583	ECOZA Approved Use Ecoza (econazole nitrate) topical foam, 1%, is indicated for the treatment of interdigital tinea pedis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum in patients 12 years of age and older. Launch Date 1982

C_max

Value	Dose	Co-administered	Analyte	Population
417 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf	24 mg 1 times / day steady-state, topical dose: 24 mg route of administration: Topical experiment type: STEADY-STATE co-administered:		ECONAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
53 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819	150 mg single, vaginal dose: 150 mg route of administration: Vaginal experiment type: SINGLE co-administered:	ECONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
81.77 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819	150 mg 1 times / day multiple, vaginal dose: 150 mg route of administration: Vaginal experiment type: MULTIPLE co-administered:	ECONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
3440 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf	24 mg 1 times / day steady-state, topical dose: 24 mg route of administration: Topical experiment type: STEADY-STATE co-administered:	ECONAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
150 mg 1 times / day multiple, vaginal Dose: 150 mg, 1 times / day Route: vaginal Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32410819	healthy, 18 - 55 years Health Status: healthy Age Group: 18 - 55 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/32410819	Sources: https://pubmed.ncbi.nlm.nih.gov/32410819

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP 110	CYP51 3	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20637317/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP51 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21114623/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY545729	https://www.001chemical.com/chem/27220-47-9
3B Scientific (Wuhan) Corp	3B2-1071	http://www.3bsc.com/index/pro_info.php?id=48135
abcr GmbH	AB437715	http://www.abcr.com/shop/en/AB437715
Achemtek	0104-009378	http://www.achemtek.com/27220-47-9
Acorn PharmaTech	ACN-037051	http://www.acornpharmatech.com/
Acros Organics	AC458630050	https://www.fishersci.com/shop/products/econazole-99-acros-organics-1/AC458630050
Acros Organics	AC458630250	https://www.fishersci.com/shop/products/econazole-99-acros-organics/AC458630250
AHH Chemical co.,ltd	MT-50766	http://www.ahhchemical.com/product/MT-50766.html
AK Scientific, Inc. (AKSCI)	J10460	http://www.aksci.com/item_detail.php?cat=J10460
AK Scientific, Inc. (AKSCI)	M369	http://www.aksci.com/item_detail.php?cat=M369
Angel Pharmatech	AG153817	http://www.angelpharmatech.com/27220-47-9.html
Angene	AGN-PC-0JK6HF	http://www.angenechemical.com/productshow/AGN-PC-0JK6HF.html
Ark Pharm	AK174005	http://www.arkpharminc.com/products/27220-47-9.html
AvaChem Scientific	2679B	http://www.avachem.com/productSearch.asp?2679B
BioSynth	W-107123	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-107123.html
BLD Pharm	BD16828	http://www.bldpharm.com/products/27220-47-9.html
Chem Scene	CS-4348	http://www.chemscene.com/27220-47-9.html
Chemspace	CSSB00000043504	https://chem-space.com/CSSB00000043504
CSNpharm	CSN12439	https://www.csnpharm.com/products/econazole.html
Debye Scientific	DB-047186	http://www.debyesci.com/cas_27220-47-9.html
eNovation Chemicals	D405419	https://www.enovationchem.com/ProductDetails.asp?ProductID=D405419
Finetech	FT-0630530	http://www.finetechnology-ind.com/prod/detail/pub/27220-47-9.html
Glentham Life Sciences	GA7153	http://www.glentham.com/products/product/GA7153/
Hairui	HR122661	http://www.hairuichem.com/en/product/27220-47-9.html
iChemical	EBD15324	http://www.ichemical.com/products/27220-47-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00244250	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00244250
LGC Standards	LGCFOR3432.00	https://www.lgcstandards.com/US/en/p/LGCFOR3432.00
LGC Standards	MM3432.00	https://www.lgcstandards.com/US/en/p/MM3432.00
MedChem Express	HY-B0885	https://www.medchemexpress.com/Econazole.html
Molcore	MC545729	https://www.molcore.com/product/27220-47-9
MuseChem	I002936	https://www.musechem.com/product/I002936.html
OChem	8326	http://www.ocheminc.com/index.php?act=psearch&pid=220E479
Parchem	28805	http://www.parchem.com/chemical-supplier-distributor/Econazole-Nitrate-018805.aspx
Shanghai Send Pharmaceutical Technology Co., Ltd	send35664	http://shsendpharm.com/
Smolecule	S591883	https://www.smolecule.com/products/s591883
THE BioTek	bt-315148	https://www.thebiotek.com/product/others/bt-315148
Vitas-M Laboratory	STL483402	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL483402&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Increase in anticoagulant effect of warfarin in a patient using econazole cream.	2006-11	17052529
Inhibition of Ca2+ influx is required for mitochondrial reactive oxygen species-induced endoplasmic reticulum Ca2+ depletion and cell death in leukemia cells.	2006-10	16849592
Effects of Ca2+ channel blockers on store-operated Ca2+ channel currents of Kupffer cells after hepatic ischemia/reperfusion injury in rats.	2006-08-07	16937441
Azole antifungals as novel chemotherapeutic agents against murine tuberculosis.	2006-08	16907718
What's your diagnosis? Nine-year-old girl with a pubic rash gone incognito.	2006-08	16873039
Cloning and characterization of CYP51 from Mycobacterium avium.	2006-08	16543605
Single-dose sertaconazole vaginal tablet treatment of vulvovaginal candidiasis.	2006-06	16863011
Econazole attenuates cytotoxicity of 1-methyl-4-phenylpyridinium by suppressing mitochondrial membrane permeability transition.	2006-05-31	16716839
The potential of azole antifungals against latent/persistent tuberculosis.	2006-05	16640573
Near-infrared spectrometry for the quantification of dermal absorption of econazole nitrate and 4-cyanophenol.	2006-04	16554957
Antimycotic influence of beta-cyclodextrin complexes--in vitro measurements using laser nephelometry in microtiter plates.	2006-03-27	16442247
What is the best way to treat tinea cruris?	2006-03	16510062
A screening method for chiral selectors that does not require covalent attachment.	2006-02-22	16478163
TRPV6 potentiates calcium-dependent cell proliferation.	2006-02	16356545
Signaling pathways influencing SLF and c-kit-mediated survival and proliferation.	2006	17003505
[Diagnosis at a glance. Leisure athlete with itchy back].	2005-12-08	16401019
Athlete's foot.	2005-12	16620478
[Congenital cutaneous candidiasis: a case report and review].	2005-12	16425712
In vitro and ex vivo antimycobacterial potential of azole drugs against Mycobacterium tuberculosis H37Rv.	2005-10-01	16143463
The role of TRPM channels in cell death.	2005-10	16025303
Molecular mechanisms of econazole-induced toxicity on human colon cancer cells: G0/G1 cell cycle arrest and caspase 8-independent apoptotic signaling pathways.	2005-10	15919146
Cytochrome P450 products and arachidonic acid-induced, non-store-operated, Ca2+ entry in cultured bovine endothelial cells.	2005-09-16	16162437
Nano-encapsulation of azole antifungals: potential applications to improve oral drug delivery.	2005-09-14	16023808
Econazole induces increases in free intracellular Ca2+ concentrations in human osteosarcoma cells.	2005-09	16235734
Effects of econazole on Ca2+ levels in and the growth of human prostate cancer PC3 cells.	2005-09	16173930
[Experimental study on apoptosis in leukemia cells induced by econazole].	2005-06	15972127
Altered expression profile of mycobacterial surface glycopeptidolipids following treatment with the antifungal azole inhibitors econazole and clotrimazole.	2005-06	15942015
Signaling pathways in the biphasic effect of ANG II on Na+/H+ exchanger in T84 cells.	2005-05	16283585
In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis.	2004-12	15608448
Poliosis associated with treatment of fungal endophthalmitis.	2004-12	15590526
Concurrent use of 5% natamycin and 2% econazole for the management of fungal keratitis.	2004-11	15502480
Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.	2004-10-15	15388173
The calcium influx pathway in rat olfactory ensheathing cells shows TRPC channel pharmacology.	2004-10-08	15364031
Inhibition of TRPM2 channels by the antifungal agents clotrimazole and econazole.	2004-10	15549272
P2Y2-receptor-mediated activation of a contralateral, lanthanide-sensitive calcium entry pathway in the human airway epithelium.	2004-09	15289296
Imidazole analogues of fluoxetine, a novel class of anti-Candida agents.	2004-07-29	15267229
Usage of antifungal drugs for therapy of genital Candida infections, purchased as over-the-counter products or by prescription: I. Analyses of a unique database.	2004-06	15739823
Epidermal growth factor inhibits 14C-alpha-methyl-D-glucopyranoside uptake in renal proximal tubule cells: involvement of PLC/PKC, p44/42 MAPK, and cPLA2.	2004-05	15040003
Thapsigargin-stimulated MAP kinase phosphorylation via CRAC channels and PLD activation: inhibitory action of docosahexaenoic acid.	2004-04-23	15094063
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.	2004-04-15	15135088
Antioxidative natural product protect against econazole-induced liver injuries.	2004-03-01	15036759
Increased calcium influx and ribosomal content correlate with resistance to endoplasmic reticulum stress-induced cell death in mutant leukemia cell lines.	2004-02-20	14660643
Co-isolation of Trichosporon inkin and Candida parapsilosis from a scalp white piedra case.	2004-02	14982118
Dermatophyte-related granular parakeratosis.	2004-02	14726826
Characteristics and a functional implication of Ca(2+)-activated K(+) current in mouse aortic endothelial cells.	2004-01	14648123
Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery.	2003-12-01	14609745
The role of calcium channels in substance P-induced contractile response in the rat iris.	2003-12	15127952
Experimental evaluation of antifungal and antiseptic agents against Rhodotorula spp.	2003-12	14641623
Effect of epidermal growth factor on phosphate uptake in renal proximal tubule cells: involvement of PKC, MAPK, and cPLA2.	2003	14610335
[Antifungal drug susceptibility of Candida causing oropharyngeal candidiasis in HIV infected patients].	2001	15773146

Patents

Sample Use Guides

In Vivo Use Guide

Topical foam, 1% is for topical use only. Ecoza topical foam, 1% is not for oral, ophthalmic, or intravaginal use. Ecoza topical foam, 1% should be applied to cover affected areas once daily for 4 weeks.

Route of Administration: Topical

In Vitro Use Guide

Minimum inhibitory concentrations (MIC) of econazole against Mycobacterium avium complex (MAC) and and a minimum bacteriocidal concentration was 4 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:21 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:21 GMT 2025`
Record UNII	6Z1Y2V4A7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ECONAZOLE

Official Name

English

NSC-187789

Preferred Name

English

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

Systematic Name

English

Econazole [WHO-DD]

Common Name

English

MICONAZOLE NITRATE IMPURITY B [EP IMPURITY]

Common Name

English

ECONAZOLE [EP MONOGRAPH]

Common Name

English

ECONAZOLE [MI]

Common Name

English

ECONAZOLE [VANDF]

Common Name

English

MICONAZOLE IMPURITY B [EP IMPURITY]

Common Name

English

1-(2,4-DICHLORO-.BETA.-((P-CHLOROBENZYL)OXY)PHENETHYL)IMIDAZOLE

Common Name

English

ECONAZOLE [MART.]

Common Name

English

econazole [INN]

Common Name

English

(±)-ECONAZOLE

Common Name

English

ECONAZOLE [USAN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175487