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
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)
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 | ( + / - ) |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/3069196
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3069196
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: synthesis and organisation of the membrane wall Sources: http://www.ncbi.nlm.nih.gov/pubmed/3537934 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Pityriasis versicolor rubra. | 2002 Mar-Apr |
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Dermatoscopy in the diagnosis of tinea nigra. | 2008 Aug 15 |
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Step-wise treatment of athlete's foot (tinea pedis) using isoconazole combined with a corticosteroid followed by isoconazole alone. | 2008 Sep |
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Balanitis with eczematous perigenital intertriginous candidosis. | 2008 Sep |
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Tinea incognito due to Trichophyton rubrum responsive to topical therapy with isoconazole plus corticosteroid cream. | 2008 Sep |
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Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay. | 2009 Sep 14 |
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Reactive oxygen species and the bacteriostatic and bactericidal effects of isoconazole nitrate. | 2013 May |
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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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6365236
for vaginal candidosis: two 300 mg isoconazole tablets
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3537934
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
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admin
on
Edited
Fri Dec 15 18:50:14 GMT 2023
by
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on
Fri Dec 15 18:50:14 GMT 2023
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Record UNII |
5AS8P3N30X
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C514
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C020382
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |