U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ECONAZOLE

SMILES

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

4.09449595E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
417 pg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3440 pg × h/mL
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
53 ng × h/mL
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
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
Doses

Doses

DosePopulationAdverse 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:
healthy, 18 - 55 years
Health Status: healthy
Age Group: 18 - 55 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Antifungal drug susceptibility of Candida causing oropharyngeal candidiasis in HIV infected patients].
2001
Effect of epidermal growth factor on phosphate uptake in renal proximal tubule cells: involvement of PKC, MAPK, and cPLA2.
2003
The role of calcium channels in substance P-induced contractile response in the rat iris.
2003 Dec
Experimental evaluation of antifungal and antiseptic agents against Rhodotorula spp.
2003 Dec
Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery.
2003 Dec 1
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.
2004 Apr 15
Thapsigargin-stimulated MAP kinase phosphorylation via CRAC channels and PLD activation: inhibitory action of docosahexaenoic acid.
2004 Apr 23
In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis.
2004 Dec
Poliosis associated with treatment of fungal endophthalmitis.
2004 Dec
Co-isolation of Trichosporon inkin and Candida parapsilosis from a scalp white piedra case.
2004 Feb
Dermatophyte-related granular parakeratosis.
2004 Feb
Increased calcium influx and ribosomal content correlate with resistance to endoplasmic reticulum stress-induced cell death in mutant leukemia cell lines.
2004 Feb 20
Characteristics and a functional implication of Ca(2+)-activated K(+) current in mouse aortic endothelial cells.
2004 Jan
Imidazole analogues of fluoxetine, a novel class of anti-Candida agents.
2004 Jul 29
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 Jun
Antioxidative natural product protect against econazole-induced liver injuries.
2004 Mar 1
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 May
Concurrent use of 5% natamycin and 2% econazole for the management of fungal keratitis.
2004 Nov
Inhibition of TRPM2 channels by the antifungal agents clotrimazole and econazole.
2004 Oct
Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.
2004 Oct 15
The calcium influx pathway in rat olfactory ensheathing cells shows TRPC channel pharmacology.
2004 Oct 8
P2Y2-receptor-mediated activation of a contralateral, lanthanide-sensitive calcium entry pathway in the human airway epithelium.
2004 Sep
Athlete's foot.
2005 Dec
[Congenital cutaneous candidiasis: a case report and review].
2005 Dec
[Diagnosis at a glance. Leisure athlete with itchy back].
2005 Dec 8
Cytochrome P450 products and arachidonic acid-induced, non-store-operated, Ca2+ entry in cultured bovine endothelial cells.
2005 Jul-Aug
[Experimental study on apoptosis in leukemia cells induced by econazole].
2005 Jun
Altered expression profile of mycobacterial surface glycopeptidolipids following treatment with the antifungal azole inhibitors econazole and clotrimazole.
2005 Jun
Signaling pathways in the biphasic effect of ANG II on Na+/H+ exchanger in T84 cells.
2005 May
The role of TRPM channels in cell death.
2005 Oct
Molecular mechanisms of econazole-induced toxicity on human colon cancer cells: G0/G1 cell cycle arrest and caspase 8-independent apoptotic signaling pathways.
2005 Oct
In vitro and ex vivo antimycobacterial potential of azole drugs against Mycobacterium tuberculosis H37Rv.
2005 Oct 1
Econazole induces increases in free intracellular Ca2+ concentrations in human osteosarcoma cells.
2005 Sep
Effects of econazole on Ca2+ levels in and the growth of human prostate cancer PC3 cells.
2005 Sep
Nano-encapsulation of azole antifungals: potential applications to improve oral drug delivery.
2005 Sep 14
Signaling pathways influencing SLF and c-kit-mediated survival and proliferation.
2006
Near-infrared spectrometry for the quantification of dermal absorption of econazole nitrate and 4-cyanophenol.
2006 Apr
Azole antifungals as novel chemotherapeutic agents against murine tuberculosis.
2006 Aug
What's your diagnosis? Nine-year-old girl with a pubic rash gone incognito.
2006 Aug
Cloning and characterization of CYP51 from Mycobacterium avium.
2006 Aug
Effects of Ca2+ channel blockers on store-operated Ca2+ channel currents of Kupffer cells after hepatic ischemia/reperfusion injury in rats.
2006 Aug 7
TRPV6 potentiates calcium-dependent cell proliferation.
2006 Feb
A screening method for chiral selectors that does not require covalent attachment.
2006 Feb 22
Single-dose sertaconazole vaginal tablet treatment of vulvovaginal candidiasis.
2006 Jun
What is the best way to treat tinea cruris?
2006 Mar
Antimycotic influence of beta-cyclodextrin complexes--in vitro measurements using laser nephelometry in microtiter plates.
2006 Mar 27
The potential of azole antifungals against latent/persistent tuberculosis.
2006 May
Econazole attenuates cytotoxicity of 1-methyl-4-phenylpyridinium by suppressing mitochondrial membrane permeability transition.
2006 May 31
Increase in anticoagulant effect of warfarin in a patient using econazole cream.
2006 Nov
Inhibition of Ca2+ influx is required for mitochondrial reactive oxygen species-induced endoplasmic reticulum Ca2+ depletion and cell death in leukemia cells.
2006 Oct
Patents

Sample Use Guides

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
Curator's Comment: Econazole inhibited the growth of all isolates of Trichophyton species in low concentrations of 2-4 micrograms/ml except one isolate of T. rubrum which was inhibited by a concentration ug/ml. https://www.ncbi.nlm.nih.gov/pubmed/2737705
Minimum inhibitory concentrations (MIC) of econazole against Mycobacterium avium complex (MAC) and and a minimum bacteriocidal concentration was 4 ug/ml.
Name Type Language
ECONAZOLE
EP   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official 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
NSC-187789
Code English
econazole [INN]
Common Name English
(±)-ECONAZOLE
Common Name English
ECONAZOLE [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175487
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
WHO-VATC QD01AC03
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
WHO-ATC D01AC03
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
WHO-ATC G01AF05
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
NCI_THESAURUS C514
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
EPA PESTICIDE CODE 600070
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
WHO-VATC QG01AF05
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
NDF-RT N0000008217
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
Code System Code Type Description
INN
3189
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
WIKIPEDIA
ECONAZOLE
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
EVMPD
SUB06450MIG
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL808
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
MESH
D004464
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
DAILYMED
6Z1Y2V4A7M
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
FDA UNII
6Z1Y2V4A7M
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
248-341-6
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
DRUG BANK
DB01127
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
DRUG CENTRAL
983
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
PUBCHEM
3198
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
NCI_THESAURUS
C61740
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
NSC
187789
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID2029872
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
CHEBI
4754
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
MERCK INDEX
M4819
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY Merck Index
IUPHAR
2446
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
RXCUI
3743
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY RxNorm
LACTMED
Econazole
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
CAS
27220-47-9
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY
SMS_ID
100000092239
Created by admin on Wed Jul 05 22:30:17 UTC 2023 , Edited by admin on Wed Jul 05 22:30:17 UTC 2023
PRIMARY