Details
Stereochemistry | RACEMIC |
Molecular Formula | C14H10ClN3S2 |
Molecular Weight | 319.832 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=C(C=CC=C1)C2CS\C(S2)=C(\C#N)N3C=CN=C3
InChI
InChIKey=ZRTQSJFIDWNVJW-WYMLVPIESA-N
InChI=1S/C14H10ClN3S2/c15-11-4-2-1-3-10(11)13-8-19-14(20-13)12(7-16)18-6-5-17-9-18/h1-6,9,13H,8H2/b14-12+
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/25285056Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/11486456
http://www.ncbi.nlm.nih.gov/pubmed/11893219
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25285056
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/11486456
http://www.ncbi.nlm.nih.gov/pubmed/11893219
In the late 1970s, Niwano et al found that introduction of an imidazole moiety onto a ketene dithioacetal structure increased its antifungal activity manifold. Lanoconazole, the compound thus generated, has been shown to have activity against a variety of fungi, including yeast, dermatophytes, and dematiaceous fungi, and has signifcant fungicidal activity against Trichophyton spp. Lanoconazole is a racemic mixture, and further studies revealed that its antifungal activity is attributed to the R-enantiomer, and the latter has at least two-fold more potent antifungal activity when compared with the racemic compound. The drug has been available for clinical use in Japan since 1994 and once-daily application to affected areas is recommended. In addition to its antifungal effect, animal data suggest that application of lanoconazole 0.5 or 1% cream is associated with accelerated wound healing
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P10613 Gene ID: 3641571.0 Gene Symbol: ERG11 Target Organism: Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Sources: http://www.ncbi.nlm.nih.gov/pubmed/10520160 |
0.036 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Lanoconazole, a new imidazole antimycotic compound, protects MAIDS mice against encephalitis caused by Cryptococcus neoformans. | 2000 Sep |
|
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11486456
1% lanoconazole cream
Route of Administration:
Topical
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25675966
The release of interleukin-8 (IL-8) from human epidermal keratinocytes stimulated by the addition of 100 μg ml(-1) β-glucan of Saccharomyces cerevisiae was significantly inhibited by lanoconazole (LCZ) at the concentration of 10(-5) mol l(-1). The release of interferon-γ and IL-2 from human peripheral blood mononuclear cells stimulated by the addition of 30 and 100 μg ml(-1) phytohemagglutinin was significantly inhibited by LCZ at the concentrations of 10(-7) and 10(-6) mol l(-1), respectively.
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C514
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ACTIVE MOIETY