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
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
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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Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes. | 1992 Nov-Dec |
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[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use]. | 2001 Oct-Dec |
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Pityriasis versicolor rubra. | 2002 Mar-Apr |
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In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis. | 2004 Dec |
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Susceptibility to some antifungal drugs of vaginal lactobacilli isolated from healthy women. | 2005 |
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Line-walking method for predicting the inhibition of P450 drug metabolism. | 2006 Jul 13 |
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Molecular typing and antifungal susceptibility of Trichophyton rubrum isolates from patients with onychomycosis pre- and post-treatment. | 2007 May |
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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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Successful treatment of tinea pedis with a topical agent containing isoconazole nitrate and diflucortolone valerate. | 2008 Sep |
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Balanitis with eczematous perigenital intertriginous candidosis. | 2008 Sep |
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Topical treatment of intertriginous candidal infection. | 2008 Sep |
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Treatment of candidal intertrigo with a topical combination of isoconazole nitrate and diflucortolone valerate. | 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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Tinea corporis treated with a combined topical therapy containing isoconazole and a corticosteroid. | 2008 Sep |
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Tinea corporis of the shin and chest successfully treated with a topical antifungal and corticosteroid cream. | 2008 Sep |
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Tinea cruris treated with a combined topical therapy containing isoconazole and a corticosteroid. | 2008 Sep |
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The effective use of isoconazole nitrate and diflucortolone valerate cream in the treatment of inguino-femoral skin fold mycosis. | 2008 Sep |
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Successful therapy of tinea cruris with topical isoconazole in combination with a corticosteroid. | 2008 Sep |
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The advantages of topical combination therapy in the treatment of inflammatory dermatomycoses. | 2008 Sep |
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Superficial dermatomycoses worldwide: multinational treatment experience with a combination of isoconazole nitrate and diflucortolone valerate. Introduction. | 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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Otomycosis: Diagnosis and treatment. | 2010 Mar 4 |
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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 16:29:38 GMT 2023
by
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on
Fri Dec 15 16:29:38 GMT 2023
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Record UNII |
GRI7WFR424
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Record Status |
Validated (UNII)
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Record Version |
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QG01AF07
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Isoconazole
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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PARENT -> IMPURITY |
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EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |