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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
Structure of LANOCONAZOLE

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+

HIDE SMILES / InChI

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10613
Gene ID: 3641571.0
Gene Symbol: ERG11
Target Organism: Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)
0.036 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

1% lanoconazole cream
Route of Administration: Topical
In Vitro Use Guide
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.
Name Type Language
LANOCONAZOLE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
(±)-.ALPHA.-((E)-4-(O-CHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE)IMIDAZOLE-1-ACETONITRILE
Common Name English
LANOCONAZOLE [JAN]
Common Name English
LANOCONAZOLE [MI]
Common Name English
Lanoconazole [WHO-DD]
Common Name English
lanoconazole [INN]
Common Name English
LANOCONAZOLE [MART.]
Common Name English
ASTAT
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 17:32:52 GMT 2023 , Edited by admin on Fri Dec 15 17:32:52 GMT 2023
Code System Code Type Description
FDA UNII
4E7858311F
Created by admin on Fri Dec 15 17:32:52 GMT 2023 , Edited by admin on Fri Dec 15 17:32:52 GMT 2023
PRIMARY
NCI_THESAURUS
C81504
Created by admin on Fri Dec 15 17:32:52 GMT 2023 , Edited by admin on Fri Dec 15 17:32:52 GMT 2023
PRIMARY
EVMPD
SUB08398MIG
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PRIMARY
CHEBI
30415
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PRIMARY
PUBCHEM
3002820
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DRUG CENTRAL
3979
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MERCK INDEX
m6678
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PRIMARY Merck Index
INN
6853
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PRIMARY
EPA CompTox
DTXSID6046428
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PRIMARY
CAS
101530-10-3
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PRIMARY
ChEMBL
CHEMBL1555126
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PRIMARY
SMS_ID
100000082554
Created by admin on Fri Dec 15 17:32:52 GMT 2023 , Edited by admin on Fri Dec 15 17:32:52 GMT 2023
PRIMARY
MESH
C072774
Created by admin on Fri Dec 15 17:32:52 GMT 2023 , Edited by admin on Fri Dec 15 17:32:52 GMT 2023
PRIMARY