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Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl4N2O.HNO3
Molecular Weight 479.141
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOCONAZOLE NITRATE

SMILES

O[N+]([O-])=O.ClC1=CC(Cl)=C(C=C1)C(CN2C=CN=C2)OCC3=C(Cl)C=CC=C3Cl

InChI

InChIKey=NNGQLSIGRSTLLU-UHFFFAOYSA-N
InChI=1S/C18H14Cl4N2O.HNO3/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;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula HNO3
Molecular Weight 63.0128
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Reactive oxygen species and the bacteriostatic and bactericidal effects of isoconazole nitrate.
2013-05
Isoconazole nitrate: a unique broad-spectrum antimicrobial azole effective in the treatment of dermatomycoses, both as monotherapy and in combination with corticosteroids.
2013-05
Otomycosis: Diagnosis and treatment.
2010-03-04
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009-09-14
Step-wise treatment of athlete's foot (tinea pedis) using isoconazole combined with a corticosteroid followed by isoconazole alone.
2008-09
Successful treatment of tinea pedis with a topical agent containing isoconazole nitrate and diflucortolone valerate.
2008-09
Balanitis with eczematous perigenital intertriginous candidosis.
2008-09
Topical treatment of intertriginous candidal infection.
2008-09
Treatment of candidal intertrigo with a topical combination of isoconazole nitrate and diflucortolone valerate.
2008-09
Tinea incognito due to Trichophyton rubrum responsive to topical therapy with isoconazole plus corticosteroid cream.
2008-09
Tinea corporis treated with a combined topical therapy containing isoconazole and a corticosteroid.
2008-09
Tinea corporis of the shin and chest successfully treated with a topical antifungal and corticosteroid cream.
2008-09
Tinea cruris treated with a combined topical therapy containing isoconazole and a corticosteroid.
2008-09
The effective use of isoconazole nitrate and diflucortolone valerate cream in the treatment of inguino-femoral skin fold mycosis.
2008-09
Successful therapy of tinea cruris with topical isoconazole in combination with a corticosteroid.
2008-09
The advantages of topical combination therapy in the treatment of inflammatory dermatomycoses.
2008-09
Superficial dermatomycoses worldwide: multinational treatment experience with a combination of isoconazole nitrate and diflucortolone valerate. Introduction.
2008-09
Dermatoscopy in the diagnosis of tinea nigra.
2008-08-15
Molecular typing and antifungal susceptibility of Trichophyton rubrum isolates from patients with onychomycosis pre- and post-treatment.
2007-05
Line-walking method for predicting the inhibition of P450 drug metabolism.
2006-07-13
Susceptibility to some antifungal drugs of vaginal lactobacilli isolated from healthy women.
2005
In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis.
2004-12
Pityriasis versicolor rubra.
2002-03-02
[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use].
2002-02-09
Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes.
1992-11-01
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.
1992-04
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 Mon Mar 31 19:22:05 GMT 2025
Edited
by admin
on Mon Mar 31 19:22:05 GMT 2025
Record UNII
5AS8P3N30X
Record Status Validated (UNII)
Record Version
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Name Type Language
R 15,454
Preferred Name English
ISOCONAZOLE NITRATE
EP   JAN   MART.   MI   WHO-DD  
Common Name English
ISOCONAZOLE NITRATE [EP MONOGRAPH]
Common Name English
R-15,454
Code English
1-(2-(2,4-DICHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)METHOXY)ETHYL)-1H-IMIDAZOLE MONONITRATE
Systematic Name English
ISOCONAZOLE NITRATE [EP IMPURITY]
Common Name English
ISOCONAZOLE NITRATE [MART.]
Common Name English
ISOCONAZOLE NITRATE [JAN]
Common Name English
ISOCONAZOLE NITRATE [MI]
Common Name English
R-15454
Code English
Isoconazole nitrate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
254-769-4
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
ALTERNATIVE
MESH
C020382
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
PUBCHEM
159968
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
NCI_THESAURUS
C98015
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID60946995
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
SMS_ID
100000090187
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1571863
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
MERCK INDEX
m6475
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY Merck Index
RXCUI
203157
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
246-051-4
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
CAS
40036-10-0
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
NON-SPECIFIC STOICHIOMETRY
CAS
24168-96-5
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
EVMPD
SUB02786MIG
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
FDA UNII
5AS8P3N30X
Created by admin on Mon Mar 31 19:22:05 GMT 2025 , Edited by admin on Mon Mar 31 19:22:05 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY