Luliconazole (CED0009854)

Record Information

Version

1.0

Creation Date

2016-05-22 06:34:23 UTC

Update Date

2026-08-19 08:29:51 UTC

Accession Number

CHEM019849

Identification

Common Name

Luliconazole

Class

Small Molecule

Description

Luliconazole is an organic compound with the formula C14H9Cl2N3S2 and an average molecular weight of 354.27 g/mol. Luliconazole belongs to the halobenzenes, a subclass of benzene and substituted derivatives within the organic compounds. It is used in healthcare, pharmaceuticals, and veterinary products as an antifungal for dermatological use, with topical application as the recorded exposure route. Mechanistically, it acts as an inhibitor of the protein target Lanosterol 14-alpha demethylase (ERG11).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lulicon	Kegg
Luzu	Kegg
4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile	MeSH
NND 502	MeSH
NND-502	MeSH
Luliconazole	MeSH
(2E)-((4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene)(1H-imidazol-1-yl)acetonitrile	MeSH

Chemical Formula

C₁₄H₉Cl₂N₃S₂

Average Molecular Mass

354.270 g/mol

Monoisotopic Mass

352.961 g/mol

CAS Registry Number

187164-19-8

IUPAC Name

2-[(2E,4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile

Traditional Name

luliconazole

SMILES

ClC1=CC(Cl)=C(C=C1)[C@@H]1CS\C(S1)=C(\C#N)N1C=CN=C1

InChI Identifier

InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1

InChI Key

YTAOBBFIOAEMLL-REQDGWNSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,3-dichlorobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Azole
Heteroaromatic compound
Dithiolane
1,3-dithiolane
Imidazole
Azacycle
Organoheterocyclic compound
Carbonitrile
Nitrile
Organonitrogen compound
Organic nitrogen compound
Organochloride
Organopnictogen compound
Hydrocarbon derivative
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:34825 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	4.27	ALOGPS
logP	4.07	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	6.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	41.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101 m³·mol⁻¹	ChemAxon
Polarizability	33.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-0059000000-22ad1255353847edb6f8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00n0-4197000000-8090cd139bab5856ee94	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9670000000-394f95a2bb3211e7f6d9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gb9-2971000000-42c7b82027517ae3b4d4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0590000000-c042e297fd18a641c944	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udj-4950000000-aa96a8338a1966448c23	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
672.0	Log mg/kg	[380:1200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
299	Antifungals for dermatological use	Healthcare, pharmaceuticals & veterinary products	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available

Pathways

3 pathways

Luliconazole Action Pathway

Luliconazole Drug Metabolism

Luliconazole Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cysteine protease ATG4A	Q8WYN0	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	Indoleamine 2,3-dioxygenase 1	P14902	Humans	Predicted (SEA)	84.3886
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	3364.49
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	2562.25
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	2945.04
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	1042.09
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	616.488
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	881.876
Click to view 3D structure	Thromboxane-A synthase	P24557	Humans	Predicted (SEA)	76.8372
Click to view 3D structure	Substance-K receptor	P21452	Humans	Predicted (SEA)	462.58
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	1007.06
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	1602.21
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	1862.23
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	2205.31
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	865.45
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	724.153
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	942.832
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	681.259
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	1419.42
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	57.842
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	1223.63
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	2737.1
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	1215.54
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	291.078
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	2699.42