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
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 activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.
1992 Apr
Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes.
1992 Nov-Dec
Pityriasis versicolor rubra.
2002 Mar-Apr
Susceptibility to some antifungal drugs of vaginal lactobacilli isolated from healthy women.
2005
Tinea corporis of the shin and chest successfully treated with a topical antifungal and corticosteroid cream.
2008 Sep
The effective use of isoconazole nitrate and diflucortolone valerate cream in the treatment of inguino-femoral skin fold mycosis.
2008 Sep
The advantages of topical combination therapy in the treatment of inflammatory dermatomycoses.
2008 Sep
Superficial dermatomycoses worldwide: multinational treatment experience with a combination of isoconazole nitrate and diflucortolone valerate. Introduction.
2008 Sep
Otomycosis: Diagnosis and treatment.
2010 Mar 4
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.
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
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WHO-ATC G01AF07
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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
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PRIMARY
MESH
C020382
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PRIMARY
PUBCHEM
3760
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FDA UNII
GRI7WFR424
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PRIMARY
RXCUI
27901
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PRIMARY RxNorm
CHEBI
82865
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PRIMARY
EPA CompTox
DTXSID7045447
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MERCK INDEX
m6475
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PRIMARY Merck Index
EVMPD
SUB08314MIG
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PRIMARY
DRUG BANK
DB08943
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NCI_THESAURUS
C83841
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PRIMARY
WIKIPEDIA
Isoconazole
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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
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PRIMARY
INN
3505
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PRIMARY
CAS
27523-40-6
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PRIMARY
ECHA (EC/EINECS)
248-508-3
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PRIMARY