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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H9Cl2N3S2
Molecular Weight 354.2799
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LULICONAZOLE

SMILES

c1cc(c(cc1Cl)Cl)[C@]2([H])CS/C(=C(/C#N)\n3ccnc3)/S2

InChI

InChIKey=YTAOBBFIOAEMLL-REQDGWNSSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/10520160 http://www.ncbi.nlm.nih.gov/pubmed/24709260

Luliconazole (trade names Luzu, Lulicon) is an imidazole antifungal drug. As a 1% topical cream, It is indicated for the treatment of athlete's foot, jock itch, and ringworm caused by dermatophytes such as Trichophyton rubrum, Microsporum gypseum and Epidermophyton floccosum. Luliconazole is an antifungal that belongs to the azole class. Although the exact mechanism of action against dermatophytes is unknown, luliconazole appears to inhibit ergosterol synthesis by inhibiting the enzyme lanosterol demethylase. Inhibition of this enzyme’s activity by azoles results in decreased amounts of ergosterol, a constituent of fungal cell membranes, and a corresponding accumulation of lanosterol. Pharmacokinetic and safety results from phase 1 studies in patients with onychomycosis have demonstrated high concentrations of luliconazole within the nail plates of the great toe and have shown that this agent is well tolerated when administered as a 10% solution.

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)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LUZU

Approved Use

LUZU (luliconazole) Cream, 1% is indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. LUZU (luliconazole) Cream, 1% is an azole antifungal indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. (1)

Launch Date

1.38438718E12
Curative
LUZU

Approved Use

LUZU (luliconazole) Cream, 1% is indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. LUZU (luliconazole) Cream, 1% is an azole antifungal indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. (1)

Launch Date

1.38438718E12
Curative
LUZU

Approved Use

LUZU (luliconazole) Cream, 1% is indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. LUZU (luliconazole) Cream, 1% is an azole antifungal indicated for the topical treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum and Epidermophyton floccosum, in patients 18 years of age and older. (1)

Launch Date

1.38438718E12
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.1 ng/mL
20 mg 1 times / day steady-state, topical
dose: 20 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.93 ng/mL
35 mg 1 times / day steady-state, topical
dose: 35 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.72 ng × h/mL
20 mg 1 times / day steady-state, topical
dose: 20 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
18.74 ng × h/mL
35 mg 1 times / day steady-state, topical
dose: 35 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.9 h
20 mg 1 times / day steady-state, topical
dose: 20 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
35 mg 1 times / day steady-state, topical
dose: 35 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
[NO STEREO] LULICONAZOLE, (+/-)-|[NO STEREO] LULICONAZOLE, (+)-|[NO STEREO] LULICONAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / day multiple, topical
Recommended
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Co-administed with::
Omeprazole(40 mg; PO; day 1 and 8)
Sources:
unhealthy, 45.05
n = 20
Health Status: unhealthy
Condition: tinea pedis
Age Group: 45.05
Sex: M+F
Population Size: 20
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
yes [Ki 0.029 uM]
likely (co-administration study)
Comment: An in vivo study in adult subjects with moderate to severe interdigital tinea pedis and tinea cruris showed that LUZU Cream, 1% is mostly a weak inhibitor of CYP2C19. In a separate trial in adolescent subjects with tinea cruris, in vivo blood levels of LUZU Cream, 1%, were seen to approach those levels sufficient to show moderate inhibition of CYP2C19
Page: 6.0
yes [Ki 0.13 uM]
yes
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Efficacy of NND-502, a novel imidazole antimycotic agent, in experimental models of Candida albicans and Aspergillus fumigatus infections.
1999 Aug
Patents

Sample Use Guides

When treating interdigital tinea pedis, a thin layer of LUZU Cream, 1% should be applied to the affected area and approximately 1 inch of the immediate surrounding area(s) once daily for two (2) weeks. When treating tinea cruris or tinea corporis, LUZU Cream, 1% should be applied to the affected area and approximately 1 inch of the immediate surrounding area(s) once daily for one (1) week.
Route of Administration: Topical
In Vitro Use Guide
Luliconazole inhibited growth of all filamentous fungi except zygomycetes at low concentrations (MIC, < or =0.004-0.125 microg/ml), with dermatophytes being most susceptible (MIC, < or =0.004-0.008 microg/ml).
Name Type Language
LULICONAZOLE
DASH   INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
LULICONAZOLE [ORANGE BOOK]
Common Name English
LULICON
Brand Name English
LULICONAZOLE [INN]
Common Name English
LULICONAZOLE [WHO-DD]
Common Name English
LULICONAZOLE [MI]
Common Name English
NND-502
Code English
(-)-(E)-((4R)-4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE)(1H-IMIDAZOL-1-YL)ACETONITRILE
Systematic Name English
LULICONAZOLE [MART.]
Common Name English
LULICONAZOLE [VANDF]
Common Name English
LULICONAZOLE [USAN]
Common Name English
PR-2699
Code English
LULICONAZOLE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
WHO-ATC D01AC18
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
NDF-RT N0000175487
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C81510
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
IUPHAR
7366
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
CAS
187164-19-8
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
INN
8161
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
MERCK INDEX
M6925
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY Merck Index
RXCUI
1482680
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL2105689
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
EPA CompTox
187164-19-8
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
PUBCHEM
3003141
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
EVMPD
SUB32138
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
DRUG BANK
DB08933
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
FDA UNII
RE91AN4S8G
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
LACTMED
Luliconazole
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY
DRUG CENTRAL
4813
Created by admin on Fri Jun 25 23:14:15 UTC 2021 , Edited by admin on Fri Jun 25 23:14:15 UTC 2021
PRIMARY