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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

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

Description

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 TargetPharmacologyConditionPotency
17.9 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ECOZA

Cmax

ValueDoseCo-administeredAnalytePopulation
417 pg/mL
24 mg 1 times / day steady-state, topical
ECONAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
53 ng × h/mL
150 mg single, vaginal
ECONAZOLE plasma
Homo sapiens
81.77 ng × h/mL
150 mg 1 times / day multiple, vaginal
ECONAZOLE plasma
Homo sapiens
3440 pg × h/mL
24 mg 1 times / day steady-state, topical
ECONAZOLE plasma
Homo sapiens

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
6Z1Y2V4A7M
Record Status Validated (UNII)
Record Version