ENILCONAZOLE

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

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

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 8297
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 8297
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19070657	Activator 1430
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 2678

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 8429	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

PubMed

Title	Date	PubMed
Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro.	2000 Jun	10806373
Evaluation of topically applied enilconazole for the treatment of dermatophytosis in a Persian cattery.	2002 Feb	11896967
Evaluation of the efficacy of oral lufenuron combined with topical enilconazole for the management of dermatophytosis in catteries.	2002 Jun 8	12081306
Intranasal infusion of enilconazole for treatment of sinonasal aspergillosis in dogs.	2002 Nov 15	12458610
Use of computed tomography to predict the outcome of a noninvasive intranasal infusion in dogs with nasal aspergillosis.	2003 Apr	12715982
[Canine onychomycosis produced by Microsporum gypseum. A case report].	2003 Dec	15456357
Allergic contact dermatitis from 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy) ethyl]-1H-imidazole in a water-based metalworking fluid.	2003 May	12868982
Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells.	2004 Apr	15064155
Treatment of dermatophytosis in dogs and cats: review of published studies.	2004 Apr	15030558
Development of an in vitro, isolated, infected spore testing model for disinfectant testing of Microsporum canis isolates.	2004 Jun	15214954
Identification of new human pregnane X receptor ligands among pesticides using a stable reporter cell system.	2006 Jun	16565514
Long-term outcomes in dogs with sinonasal aspergillosis treated with intranasal infusions of enilconazole.	2007 Jan-Feb	17209083
Update on canine sinonasal aspergillosis.	2007 Sep	17693205
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Enilconazole treatment of horses with superficial Aspergillus spp. rhinitis.	2008 Sep-Oct	18844830
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 Aug	19117582
A lufenuron pre-treatment may enhance the effects of enilconazole or griseofulvin in feline dermatophytosis?	2009 Feb	18684653
CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides.	2009 Feb 10	19070657
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 Feb 19	19124165
A concentration addition model for the activation of the constitutive androstane receptor by xenobiotic mixtures.	2009 Jan	18832183
Antifungal activity of tea tree oil from Melaleuca alternifolia against Trichophyton equinum: an in vivo assay.	2009 Nov	19403294
Efficacy of intrasinusal administration of bifonazole cream alone or in combination with enilconazole irrigation in canine sino-nasal aspergillosis: 17 cases.	2010 Feb	20436862
Antimycotic effectiveness against dermatophytes: comparison of two in vitro tests.	2010 Jun	20490661
Eradication of feline dermatophytosis in a shelter: a field study.	2010 Jun	19706005
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010 Mar 15	20143881
Medical management of Trichophyton dermatophytosis using a novel treatment regimen in L'Hoest's monkeys (Cercopithecus lhoesti).	2010 Nov 27	21262652
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.	2011 Feb 27	21115097
Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens.	2011 Jun	21310686
Environmental impact on vascular development predicted by high-throughput screening.	2011 Nov	21788198
Potential of an in vitro toolbox combined with exposure data as a first step for the risk assessment of dietary chemical contaminants.	2011 Sep	21762035
Inhibitory effects of azole-type fungicides on interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.	2012 Mar 15	22289359
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.	2014 Sep	25028461
Cell-Based High-Throughput Screening for Aromatase Inhibitors in the Tox21 10K Library.	2015 Oct	26141389
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 Apr	26359731

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.

Name

Type

Language

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

ENILCONAZOLE FOR VETERINARY USE

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