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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
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
Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes.
1992 Nov-Dec
[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use].
2001 Oct-Dec
Pityriasis versicolor rubra.
2002 Mar-Apr
Dermatoscopy in the diagnosis of tinea nigra.
2008 Aug 15
Successful treatment of tinea pedis with a topical agent containing isoconazole nitrate and diflucortolone valerate.
2008 Sep
Tinea corporis treated with a combined topical therapy containing isoconazole and a corticosteroid.
2008 Sep
Tinea corporis of the shin and chest successfully treated with a topical antifungal and corticosteroid cream.
2008 Sep
Tinea cruris treated with a combined topical therapy containing isoconazole and a corticosteroid.
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
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.
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
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PRIMARY
PUBCHEM
159968
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PRIMARY
NCI_THESAURUS
C98015
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PRIMARY
EPA CompTox
DTXSID60946995
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PRIMARY
SMS_ID
100000090187
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PRIMARY
ChEMBL
CHEMBL1571863
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PRIMARY
MERCK INDEX
m6475
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PRIMARY Merck Index
RXCUI
203157
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PRIMARY RxNorm
ECHA (EC/EINECS)
246-051-4
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PRIMARY
CAS
40036-10-0
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NON-SPECIFIC STOICHIOMETRY
CAS
24168-96-5
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PRIMARY
EVMPD
SUB02786MIG
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PRIMARY
FDA UNII
5AS8P3N30X
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PRIMARY