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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
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
Pityriasis versicolor rubra.
2002 Mar-Apr
Dermatoscopy in the diagnosis of tinea nigra.
2008 Aug 15
Step-wise treatment of athlete's foot (tinea pedis) using isoconazole combined with a corticosteroid followed by isoconazole alone.
2008 Sep
Balanitis with eczematous perigenital intertriginous candidosis.
2008 Sep
Tinea incognito due to Trichophyton rubrum responsive to topical therapy with isoconazole plus corticosteroid cream.
2008 Sep
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
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 18:50:14 GMT 2023
Edited
by admin
on Fri Dec 15 18:50:14 GMT 2023
Record UNII
5AS8P3N30X
Record Status Validated (UNII)
Record Version
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Name Type Language
ISOCONAZOLE NITRATE
EP   JAN   MART.   MI   WHO-DD  
Common Name English
R 15,454
Code 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 Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
254-769-4
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
ALTERNATIVE
MESH
C020382
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
PUBCHEM
159968
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
NCI_THESAURUS
C98015
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID60946995
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
SMS_ID
100000090187
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1571863
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
MERCK INDEX
m6475
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY Merck Index
RXCUI
203157
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
246-051-4
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
CAS
40036-10-0
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
24168-96-5
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
EVMPD
SUB02786MIG
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
FDA UNII
5AS8P3N30X
Created by admin on Fri Dec 15 18:50:14 GMT 2023 , Edited by admin on Fri Dec 15 18:50:14 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY