U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl4N2O
Molecular Weight 416.129
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOCONAZOLE

SMILES

ClC1=CC(Cl)=C(C=C1)C(CN2C=CN=C2)OCC3=C(Cl)C=CC=C3Cl

InChI

InChIKey=MPIPASJGOJYODL-UHFFFAOYSA-N
InChI=1S/C18H14Cl4N2O/c19-12-4-5-13(17(22)8-12)18(9-24-7-6-23-11-24)25-10-14-15(20)2-1-3-16(14)21/h1-8,11,18H,9-10H2

HIDE SMILES / InChI

Molecular Formula C18H14Cl4N2O
Molecular Weight 416.129
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Isoconazole is structurally related to miconazole and econazole and was synthesized by Janssen Pharmaceutica. The compound has been marketed in several countries, but not in the United States. It has broad-spectrum activity in vitro against dermatophytes, pathogenic yeasts, pathogenic filamentous fungi, gram-positive bacteria, and trichomonads . The mode of action appears to include rapid reduction in ATP concentrations caused by damage to the fungal cell membrane. Isoconazole interacted with the cell wall and caused convolutions and wrinkles. Isoconazole also inhibited the enzyme-catalyzed release of spheroplasts from young yeast cells. A recent study has demonstrated that application of the free base of isoconazole in combination with a volatile/nonvolatile vehicle, e.g., ethanol/propylene glycol, can increase drug bioavailability in the skin. This observation may lead to newer formulations of isoconazole and broaden its use for topical (e.g., spray) treatment of yeast and dermatophytic infections. Dermatophytic Isoconazole has been developed and marketed primarily as a once-a-day, topical anti-Candida agent for the treatment of vaginal candidiasis. Studies evaluating isoconazole have demonstrated that 80 to 90% of patients with vaginal candidiasis who were treated once a day with the drug remained clinically and mycologically cured. Following insertion of two 300-mg tablets, concentrations of isoconazole in the vagina remained above minimum inhibitory and minimum fungicidal levels for at least 72 h. Isoconazole has been developed and marketed primarily as a once-a-day, topical anti-Candida agent for the treatment of vaginal candidiasis. In clinical studies, very little of the drug entered the blood after a single vaginal application of a 600-mg dose; the same dose did not adversely affect intestinal flora by inducing a proliferation of yeast like species following prolonged administration. Studies evaluating demonstrated that 80 90% of patients.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: synthesis and organisation of the membrane wall
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis.
2004 Dec
Susceptibility to some antifungal drugs of vaginal lactobacilli isolated from healthy women.
2005
Dermatoscopy in the diagnosis of tinea nigra.
2008 Aug 15
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
Otomycosis: Diagnosis and treatment.
2010 Mar 4
Reactive oxygen species and the bacteriostatic and bactericidal effects of isoconazole nitrate.
2013 May
Isoconazole nitrate: a unique broad-spectrum antimicrobial azole effective in the treatment of dermatomycoses, both as monotherapy and in combination with corticosteroids.
2013 May
Patents

Sample Use Guides

In Vivo Use Guide
for vaginal candidosis: two 300 mg isoconazole tablets
Route of Administration: Vaginal
In Vitro Use Guide
At low concentrations (1 microgram/ml, 10 microgram/ml), isoconazole induced a blockade of cell division by its fungicidal action on synthesis and organisation of the membrane wall. At higher concentrations (50 microgram/ml; 100 micrograms/ml), isoconazole induces total necrosis and death.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:29:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:29:38 GMT 2023
Record UNII
GRI7WFR424
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOCONAZOLE
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
ISOCONAZOLE [EP MONOGRAPH]
Common Name English
ISOCONAZOLE [USAN]
Common Name English
MICONAZOLE IMPURITY D [EP IMPURITY]
Common Name English
1-[2,4-Dichloro-β-[(2,6-dichlorobenzyl)oxy]phenethyl]imidazole
Systematic Name English
R-15454 FREE BASE
Code English
MICONAZOLE 2,6-ISOMER
Common Name English
ISOCONAZOLE [MI]
Common Name English
1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)METHOXY)ETHYL)-
Systematic Name English
1-(2-((2,6-DICHLOROBENZYL)OXY)-2-(2,4-DICHLOROPHENYL)ETHYL)-1H-IMIDAZOLE
Systematic Name English
MICONAZOLE NITRATE IMPURITY D [EP IMPURITY]
Common Name English
ISOCONAZOLE [MART.]
Common Name English
ISOCONAZOLE [EP IMPURITY]
Common Name English
R15454 FREE BASE
Code English
Isoconazole [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QD01AC05
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
WHO-ATC G01AF07
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
WHO-ATC D01AC05
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
WHO-VATC QG01AF07
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
Code System Code Type Description
SMS_ID
100000082808
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
MESH
C020382
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
PUBCHEM
3760
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
FDA UNII
GRI7WFR424
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
RXCUI
27901
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY RxNorm
CHEBI
82865
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045447
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
MERCK INDEX
m6475
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY Merck Index
EVMPD
SUB08314MIG
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
DRUG BANK
DB08943
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
NCI_THESAURUS
C83841
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
WIKIPEDIA
Isoconazole
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1571863
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
DRUG CENTRAL
3309
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
INN
3505
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
CAS
27523-40-6
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
248-508-3
Created by admin on Fri Dec 15 16:29:38 GMT 2023 , Edited by admin on Fri Dec 15 16:29:38 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY