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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

c1cc(ccc1COC(Cn2ccnc2)c3ccc(cc3Cl)Cl)Cl

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
Synergy between 6-amino-2-n-pentylthiobenzothiazole and ergosterol biosynthesis-inhibiting antimycotics against Candida albicans in vitro.
2000 Jul
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.
2001 Aug
Diacylglycerol activates the influx of extracellular cations in T-lymphocytes independently of intracellular calcium-store depletion and possibly involving endogenous TRP6 gene products.
2002 May 15
Effect of epidermal growth factor on phosphate uptake in renal proximal tubule cells: involvement of PKC, MAPK, and cPLA2.
2003
Experimental evaluation of antifungal and antiseptic agents against Rhodotorula spp.
2003 Dec
A population-based case-control teratological study of vaginal econazole treatment during pregnancy.
2003 Dec 10
Antifungal agents of use in animal health--chemical, biochemical and pharmacological aspects.
2003 Feb
[Vulvovaginal candidiasis and sensitivity of pathogens to antimycotics].
2003 Jan
Enhanced econazole penetration into human nail by 2-n-nonyl-1,3-dioxolane.
2003 Jan
Candidemia and the susceptibility pattern of Candida isolates in blood.
2003 Oct
Enlarging pigmented patches on the hand.
2003 Oct
A randomised clinical trial comparing 2% econazole and 5% natamycin for the treatment of fungal keratitis.
2003 Oct
Dermatophyte-related granular parakeratosis.
2004 Feb
Characteristics and a functional implication of Ca(2+)-activated K(+) current in mouse aortic endothelial cells.
2004 Jan
Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.
2004 Oct 15
Nano-encapsulation of azole antifungals: potential applications to improve oral drug delivery.
2005 Sep 14
What's your diagnosis? Nine-year-old girl with a pubic rash gone incognito.
2006 Aug
Single-dose sertaconazole vaginal tablet treatment of vulvovaginal candidiasis.
2006 Jun
What is the best way to treat tinea cruris?
2006 Mar
Increase in anticoagulant effect of warfarin in a patient using econazole cream.
2006 Nov
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
ECONAZOLE [EP MONOGRAPH]
Common Name English
ECONAZOLE [MI]
Common Name English
ECONAZOLE [VANDF]
Common Name English
ECONAZOLE [MART.]
Common Name English
NSC-187789
Code English
ECONAZOLE [INN]
Common Name English
ECONAZOLE [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175487
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
WHO-VATC QD01AC03
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
WHO-ATC D01AC03
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
WHO-ATC G01AF05
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
EPA PESTICIDE CODE 600070
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
WHO-VATC QG01AF05
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
NDF-RT N0000008217
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
Code System Code Type Description
INN
3189
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
WIKIPEDIA
ECONAZOLE
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
EVMPD
SUB06450MIG
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL808
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
MESH
D004464
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
FDA UNII
6Z1Y2V4A7M
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
248-341-6
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
DRUG BANK
DB01127
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
DRUG CENTRAL
983
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
PUBCHEM
3198
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
NCI_THESAURUS
C61740
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
EPA CompTox
27220-47-9
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
MERCK INDEX
M4819
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY Merck Index
IUPHAR
2446
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
RXCUI
3743
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY RxNorm
LACTMED
Econazole
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY
CAS
27220-47-9
Created by admin on Fri Jun 25 21:18:01 UTC 2021 , Edited by admin on Fri Jun 25 21:18:01 UTC 2021
PRIMARY