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Details

Stereochemistry RACEMIC
Molecular Formula C14H14Cl2N2O.HNO3
Molecular Weight 360.193
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENILCONAZOLE NITRATE

SMILES

O[N+]([O-])=O.ClC1=CC(Cl)=C(C=C1)C(CN2C=CN=C2)OCC=C

InChI

InChIKey=KJTYJTCKKSDSQF-UHFFFAOYSA-N
InChI=1S/C14H14Cl2N2O.HNO3/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16;2-1(3)4/h2-6,8,10,14H,1,7,9H2;(H,2,3,4)

HIDE SMILES / InChI
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

PubMed

TitleDatePubMed
Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro.
2000 Jun
Evaluation of topically applied enilconazole for the treatment of dermatophytosis in a Persian cattery.
2002 Feb
Evaluation of the efficacy of oral lufenuron combined with topical enilconazole for the management of dermatophytosis in catteries.
2002 Jun 8
[Canine onychomycosis produced by Microsporum gypseum. A case report].
2003 Dec
Allergic contact dermatitis from 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy) ethyl]-1H-imidazole in a water-based metalworking fluid.
2003 May
Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans.
2004 Aug
Development of an in vitro, isolated, infected spore testing model for disinfectant testing of Microsporum canis isolates.
2004 Jun
[Incidence, immunity and treatment of feline dermatophytosis].
2005 May
Dysmorphogenic effects of some fungicides derived from the imidazole on rat embryos cultured in vitro.
2006 Jan
Combined clotrimazole irrigation and depot therapy for canine nasal aspergillosis.
2006 Jun
Identification of new human pregnane X receptor ligands among pesticides using a stable reporter cell system.
2006 Jun
Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.
2006 Nov
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 May
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
A lufenuron pre-treatment may enhance the effects of enilconazole or griseofulvin in feline dermatophytosis?
2009 Feb
Successful treatment of a sinonasal cryptococcal granuloma in a horse.
2009 Feb 15
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
Antifungal activity of tea tree oil from Melaleuca alternifolia against Trichophyton equinum: an in vivo assay.
2009 Nov
Eradication of feline dermatophytosis in a shelter: a field study.
2010 Jun
Medical management of Trichophyton dermatophytosis using a novel treatment regimen in L'Hoest's monkeys (Cercopithecus lhoesti).
2010 Nov 27
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011 Feb 27
Environmental impact on vascular development predicted by high-throughput screening.
2011 Nov
Inhibitory effects of azole-type fungicides on interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.
2012 Mar 15
Patents

Sample Use Guides

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
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 NITRATE
Common Name English
1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPENYLOXY)ETHYL)-, (±)-, MONONITRATE
Systematic Name English
NSC-187790
Code English
R-18531
Code English
IMAZALIL NITRATE [ISO]
Common Name English
SEB-1377
Code English
1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-(2-PROPEN-1-YLOXY)ETHYL)-, NITRATE (1:1)
Systematic Name English
IMAZALIL NITRATE
ISO  
Common Name English
Code System Code Type Description
FDA UNII
47U0Y5DQ7I
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
CAS
35554-46-2
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
SUPERSEDED
ALANWOOD
imazalil nitrate
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
PUBCHEM
443088
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
CAS
83833-36-7
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID0058487
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
NSC
187790
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
PRIMARY
CAS
33586-66-2
Created by admin on Sat Dec 16 07:50:44 GMT 2023 , Edited by admin on Sat Dec 16 07:50:44 GMT 2023
SUPERSEDED