ENILCONAZOLE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H14Cl2N2O
Molecular Weight	297.18
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(C(CN2C=CN=C2)OCC=C)C(Cl)=C1

InChI

InChIKey=PZBPKYOVPCNPJY-UHFFFAOYSA-N

InChI=1S/C14H14Cl2N2O/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16/h2-6,8,10,14H,1,7,9H2

HIDE SMILES / InChI

Molecular Formula	C14H14Cl2N2O
Molecular Weight	297.18
Charge	0
Count

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014130.pdf | https://www.drugs.com/vet/imaverol-can.html

Enilconazole is a synthetic broad-spectrum antimycotic with a high activity against most of the common dermatophytes and various other fungi and yeasts. It is a selective inhibitor of ergosterol biosynthesis, an essential component of the cell membrane of fungi and yeasts. This results in irreversible changes which are the origin of the fungicidal effect. Enilconazole is marketed under the brand name Imaverol among others. Imaverol concentrated solution is a synthetic antimycotic with a potent antifungal action against dermatophytes such as: Trichophyton verrucosum, Trichophyton mentagrophytes, Trichophyton equinum, and Microsporum canis in horses and dogs.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19070657	Inhibitor 8504
Cytochrome P450, fungi 3 Target ID: Cytochrome P450, fungi Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014130.pdf \| https://www.researchgate.net/publication/229178723_Antifungal_mode_of_action_of_imazalil	Inhibitor 8504
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19070657	Activator 1447
Nuclear receptor subfamily 1 group I member 2 8 Target ID: O75469\|\|\|Q9UJ26 Gene ID: 8856.0 Gene Symbol: NR1I2 Target Organism: Homo sapiens (Human) Sources: http://www.t3db.ca/toxins/T3D3860 \| https://www.ncbi.nlm.nih.gov/pubmed/21115097	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatomycosis 20 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014130.pdf	Curative		Approved 8583	IMAVEROL Approved Use IMAVEROL concentrated solution is a synthetic antimycotic with a potent antifungal action against dermatophytes such as: Trichophyton verrucosum, Trichophyton mentagrophytes, Trichophyton equinum, and Microsporum canis in horses and dogs. Launch Date 2012

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153		CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 1.0	yes [IC50 0.1003 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 3.0	yes [IC50 0.3869 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 3.0	yes [IC50 0.6326 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 4.0	yes [IC50 1.7888 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 6.0	yes [IC50 4.4931 uM]
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21762035/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/37175#section=Biological-Test-Results Page: 14.0

PubMed

Title	Date	PubMed
Effects of Common Pesticides on Prostaglandin D2 (PGD2) Inhibition in SC5 Mouse Sertoli Cells, Evidence of Binding at the COX-2 Active Site, and Implications for Endocrine Disruption.	2016-04	26359731
Cell-Based High-Throughput Screening for Aromatase Inhibitors in the Tox21 10K Library.	2015-10	26141389
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.	2014-09	25028461
Inhibitory effects of azole-type fungicides on interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.	2012-03-15	22289359
Environmental impact on vascular development predicted by high-throughput screening.	2011-11	21788198
Potential of an in vitro toolbox combined with exposure data as a first step for the risk assessment of dietary chemical contaminants.	2011-09	21762035
Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens.	2011-06	21310686
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.	2011-02-27	21115097
Medical management of Trichophyton dermatophytosis using a novel treatment regimen in L'Hoest's monkeys (Cercopithecus lhoesti).	2010-11-27	21262652
Antimycotic effectiveness against dermatophytes: comparison of two in vitro tests.	2010-06	20490661
Eradication of feline dermatophytosis in a shelter: a field study.	2010-06	19706005
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010-03-15	20143881
Efficacy of intrasinusal administration of bifonazole cream alone or in combination with enilconazole irrigation in canine sino-nasal aspergillosis: 17 cases.	2010-02	20436862
Antifungal activity of tea tree oil from Melaleuca alternifolia against Trichophyton equinum: an in vivo assay.	2009-11	19403294
A zoospore inhibition technique to evaluate the activity of antifungal compounds against Batrachochytrium dendrobatidis and unsuccessful treatment of experimentally infected green tree frogs (Litoria caerulea) by fluconazole and benzalkonium chloride.	2009-08	19117582
Effects of the azole fungicide Imazalil on the development of the ascidian Ciona intestinalis (Chordata, Tunicata): morphological and molecular characterization of the induced phenotype.	2009-02-19	19124165
Successful treatment of a sinonasal cryptococcal granuloma in a horse.	2009-02-15	19222362
CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides.	2009-02-10	19070657
A lufenuron pre-treatment may enhance the effects of enilconazole or griseofulvin in feline dermatophytosis?	2009-02	18684653
A concentration addition model for the activation of the constitutive androstane receptor by xenobiotic mixtures.	2009-01	18832183
Enilconazole treatment of horses with superficial Aspergillus spp. rhinitis.	2008-10-11	18844830
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Update on canine sinonasal aspergillosis.	2007-09	17693205
Correlation between digestion of the lipid phase of smedds and release of the anti-HIV drug UC 781 and the anti-mycotic drug enilconazole from smedds.	2007-05	17158039
Long-term outcomes in dogs with sinonasal aspergillosis treated with intranasal infusions of enilconazole.	2007-01-09	17209083
Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles.	2006-11-10	16989930
Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.	2006-11	17081805
Surgical treatment of canine nasal aspergillosis by rhinotomy combined with enilconazole infusion and oral itraconazole.	2006-06	16761984
Combined clotrimazole irrigation and depot therapy for canine nasal aspergillosis.	2006-06	16761982
Identification of new human pregnane X receptor ligands among pesticides using a stable reporter cell system.	2006-06	16565514
Dysmorphogenic effects of some fungicides derived from the imidazole on rat embryos cultured in vitro.	2006-01	16159706
[Incidence, immunity and treatment of feline dermatophytosis].	2005-05	15929601
Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans.	2004-08	15554355
Development of an in vitro, isolated, infected spore testing model for disinfectant testing of Microsporum canis isolates.	2004-06	15214954
Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells.	2004-04	15064155
Treatment of dermatophytosis in dogs and cats: review of published studies.	2004-04	15030558
[Canine onychomycosis produced by Microsporum gypseum. A case report].	2003-12	15456357
Allergic contact dermatitis from 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy) ethyl]-1H-imidazole in a water-based metalworking fluid.	2003-05	12868982
Use of computed tomography to predict the outcome of a noninvasive intranasal infusion in dogs with nasal aspergillosis.	2003-04	12715982
Intranasal infusion of enilconazole for treatment of sinonasal aspergillosis in dogs.	2002-11-15	12458610
Evaluation of the efficacy of oral lufenuron combined with topical enilconazole for the management of dermatophytosis in catteries.	2002-06-08	12081306
Evaluation of topically applied enilconazole for the treatment of dermatophytosis in a Persian cattery.	2002-02	11896967
Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro.	2000-06	10806373

Patents

Sample Use Guides

In Vivo Use Guide

The concentrated Imaverol (Enilconazole) is diluted in 50 parts of lukewarm water, which yields a 0.2% emulsion. Dispose of all unused diluted solutions.Dermatophytes will extend into the hair follicles. Possible crusts must therefore be removed with a hard brush, which has been soaked in the diluted IMAVEROL emulsion. It is highly recommended that the animal be sprayed entirely at the first treatment so as to reach the subclinical lesions as well.Horse: The lesions and surrounding skin are to be washed with the diluted emulsion 4 times at 3 to 4 day intervals.Dog: The animals are to be washed with the diluted emulsion 4 times at 3 to 4 day intervals.While doing this, one should rub thoroughly in the direction opposite to the hair growth to make sure that the skin is thoroughly wet. For the same reason, it is recommended to clip long-haired dogs prior to treatment.

Route of Administration: Topical

In Vitro Use Guide

A. niger strains were most susceptible to enilconazole. MIC ranged from 0.0625 to 0.5 ug/ml for enilconazole, with MIC90-0.5 ug/ml and MIC50-0.125 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:34:48 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:48 GMT 2025`
Record UNII	6K0NOF3XQ6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENILCONAZOLE FOR VETERINARY USE

Preferred Name

English

ENILCONAZOLE

Official Name

English

1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPENYLOXY)ETHYL)-, (±)-

Systematic Name

English

FLORASAN

Brand Name

English

NUZONE

Brand Name

English

ENILCONAZOLE FOR VETERINARY USE [EP MONOGRAPH]

Common Name

English

R 23,979

Code

English

MAGNATE

Brand Name

English

ENILCONAZOLE [USAN]

Common Name

English

R-23979

Code

English

ENILCONAZOLE [MART.]

Common Name

English

1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPEN-1-YLOXY)ETHYL)-

Systematic Name

English

AMOLDEN MP 100

Brand Name

English

1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPEN-1-YLOXY)ETHYL)-1H-IMIDAZOLE

Systematic Name

English

CGA-41333

Code

English

IMAZALIL

Common Name

English

FRESHGARD

Brand Name

English

(R,S)-1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPENYLOXY)ETHYL)-1H-IMIDAZOLE

Common Name

English

FUNGAFLOR

Brand Name

English

enilconazole [INN]

Common Name

English

DECCOSIL

Brand Name

English

FLOPRO IMZ

Brand Name

English

IMAVEROL

Brand Name

English

FUNGAZIL

Brand Name

English

CLINAFARM

Brand Name

English

ENILCONAZOLE [MI]

Common Name

English

IMAZALIL [ISO]

Common Name

English

BROMAZIL

Brand Name

English

ENILCONAZOLE [HSDB]

Common Name

English

DECCOZIL

Brand Name

English

(±)-1-(.BETA.-(ALLYLOXY)-2,4-DICHLOROPHENETHYL)-IMIDAZOLE

Systematic Name

English

NSC-759313

Code

English

(RS)-1-(.BETA.-ALLYLOXY-2,4-DICHLOROPHENETHYL)IMIDAZOLE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514