EBERCONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H14Cl2N2
Molecular Weight	329.223
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC(Cl)=C2C(N3C=CN=C3)C4=CC=CC=C4CCC2=C1

InChI

InChIKey=MPTJIDOGFUQSQH-UHFFFAOYSA-N

InChI=1S/C18H14Cl2N2/c19-14-9-13-6-5-12-3-1-2-4-15(12)18(17(13)16(20)10-14)22-8-7-21-11-22/h1-4,7-11,18H,5-6H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22421664

Eberconazole is an antifungal drug with broad antimicrobial spectrum of activity. The drug was developed and approved in Spain (Ebernet 1% cream) for the treatment of tinea. Eberconazole exerts fungicidal or fungistatic activity depending on concentration, being fungicidal at higher concentration and fungistatic at lower concentrations. Eberconazole prevents fungal growth by inhibiting ergosterol synthesis, an essential component of the fungal cytoplasmic membrane leading to structural and functional changes. It prevents the fungal ergosterol synthesis by inhibiting lanosterol 14alpha-demethylase enzyme that is responsible for the formation of 14 alpha-methylsterols (precursor of ergosterols).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Lanosterol 14-alpha demethylase 13 Target ID: Lanosterol 14-alpha demethylase Sources: https://www.ncbi.nlm.nih.gov/pubmed/22421664	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tinea corporis 19 Sources: https://www.aemps.gob.es/cima/pdfs/es/p/65966/Prospecto_65966.html.pdf	Curative	Approved 8429	EBERNET Approved Use EBERNET 1% cream is indicated in the cutaneous treatment of the following infections caused by Fungi: Tinea corporis, Tinea cruris and Tinea pedis. Launch Date 2004
Tinea cruris 11 Sources: https://www.aemps.gob.es/cima/pdfs/es/p/65966/Prospecto_65966.html.pdf	Curative	Approved 8429	EBERNET Approved Use EBERNET 1% cream is indicated in the cutaneous treatment of the following infections caused by Fungi: Tinea corporis, Tinea cruris and Tinea pedis. Launch Date 2004
Tinea pedis 28 Sources: https://www.aemps.gob.es/cima/pdfs/es/p/65966/Prospecto_65966.html.pdf	Curative	Approved 8429	EBERNET Approved Use EBERNET 1% cream is indicated in the cutaneous treatment of the following infections caused by Fungi: Tinea corporis, Tinea cruris and Tinea pedis. Launch Date 2004

PubMed

Title	Date	PubMed
[Topical treatment with eberconazole of the experimental guinea pig cutaneous candidosis.].	1999 Mar	18473592
In vitro susceptibilities of clinical yeast isolates to the new antifungal eberconazole compared with their susceptibilities to clotrimazole and ketoconazole.	1999 May	10223946
In vitro activities of the new antifungal drug eberconazole and three other topical agents against 200 strains of dermatophytes.	2003 Nov	14605165
Evaluation of disk diffusion method for determining eberconazole susceptibility of dermatophytes and influence of culture medium.	2005 May	15855542
Eberconazole--pharmacological and clinical review.	2012 Mar-Apr	22421664

Patents

Sample Use Guides

In Vivo Use Guide

Eberconazole (Ebernet 1% cream) should be applied twice a day for 4 weeks. The cream should be applied in sufficient quantity to cover the lesion and surroundings, and should be distributed with the aid of a light massage.

Route of Administration: Topical

In Vitro Use Guide

Antifungal activity of eberconazole was tested against 200 strains of dermatophytes. The MIC50 values were 0.06 ug/ml (E. floccosum, M. audouinii, M. canis, M. gypseum, T. ajelloi, T. violaceum), 0.03 ug/ml (M. ferrugineum, M. fulvum, T. balcaneum), 0.25 ug/ml (T. erinacei), 0.125 ug/ml (T. interdigitale, T. mentagrophytes, T. rubrum, T. simii, T. tonsurans).

Name

Type

Language

EBERCONAZOLE

Official Name

English

Eberconazole [WHO-DD]

Common Name

English

eberconazole [INN]

Common Name

English

(±)-1-(2,4-DICHLORO-10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YL)IMIDAZOLE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QD01AC17