EBERCONAZOLE NITRATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H14Cl2N2.HNO3
Molecular Weight	392.236
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[N+]([O-])=O.ClC1=CC(Cl)=C2C(N3C=CN=C3)C4=CC=CC=C4CCC2=C1

InChI

InChIKey=DPHMSVRBAXJSPF-UHFFFAOYSA-N

InChI=1S/C18H14Cl2N2.HNO3/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;2-1(3)4/h1-4,7-11,18H,5-6H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	C18H14Cl2N2
Molecular Weight	329.223
Charge	0
Count

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

Molecular Formula	HNO3
Molecular Weight	63.0128
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 15 Target ID: Lanosterol 14-alpha demethylase Sources: https://www.ncbi.nlm.nih.gov/pubmed/22421664	Inhibitor 8504

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 8583	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 8583	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 8583	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

Doses

Dose	Population	Adverse events
2 % 2 times / day multiple, topical Highest studied dose Dose: 2 %, 2 times / day Route: topical Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/	Other AEs: Burning skin, Itching... Other AEs: Burning skin (grade 1, 6.7%) Itching (grade 1, 6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/

AEs

AE	Significance	Dose	Population
Burning skin	grade 1, 6.7%	2 % 2 times / day multiple, topical Highest studied dose Dose: 2 %, 2 times / day Route: topical Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/
Itching	grade 1, 6.7%	2 % 2 times / day multiple, topical Highest studied dose Dose: 2 %, 2 times / day Route: topical Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8559197/

PubMed

Title	Date	PubMed
Eberconazole--pharmacological and clinical review.	2012-03-17	22421664
Evaluation of disk diffusion method for determining eberconazole susceptibility of dermatophytes and influence of culture medium.	2005-05	15855542
In vitro activities of the new antifungal drug eberconazole and three other topical agents against 200 strains of dermatophytes.	2003-11	14605165
In vitro susceptibilities of clinical yeast isolates to the new antifungal eberconazole compared with their susceptibilities to clotrimazole and ketoconazole.	1999-05	10223946
[Topical treatment with eberconazole of the experimental guinea pig cutaneous candidosis.].	1999-03	18473592

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).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 13:54:33 GMT 2025` Edited by `admin` on `Wed Apr 02 13:54:33 GMT 2025`
Record UNII	LSL8E59V2V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-(2,4-DICHLORO-10,11-DIHYDRO-5H-DIBENZO(A,D)(7)ANNULEN-5-YL)-1H-IMIDAZOLE NITRATE (1:1)

Preferred Name

English

EBERCONAZOLE NITRATE

Common Name

English

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

Common Name

English

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

Common Name

English

1-(4,6-DICHLORO-2-TRICYCLO(9.4.0.03,8)PENTADECA-1(15),3(8),4,6,11,13-HEXAENYL)IMIDAZOLE;NITRIC ACID

Common Name

English

Code System Code Type Description

SMS_ID

100000170416