LULICONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H9Cl2N3S2
Molecular Weight	354.277
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C([C@@H]2CS\C(S2)=C(\C#N)N3C=CN=C3)C(Cl)=C1

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

Molecular Formula	C14H9Cl2N3S2
Molecular Weight	354.277
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Lanosterol 14-alpha demethylase 13 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	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tinea pedis 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	Curative	Approved 8429	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 2013
Tinea cruris 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	Curative	Approved 8429	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 2013
Tinea corporis 19 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	Curative	Approved 8429	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 2013
Onychomycosis 18 Sources: https://clinicaltrials.gov/ct2/show/NCT01044381	Curative	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23545529/	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
1.72 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23545529/	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
19.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23545529/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204153s000lbl.pdf	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

Dose	Population	Adverse 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: https://clinicaltrials.gov/ct2/show/NCT02394340	unhealthy, 45.05 n = 20 Health Status: unhealthy Condition: tinea pedis Age Group: 45.05 Sex: M+F Population Size: 20 Sources: https://clinicaltrials.gov/ct2/show/NCT02394340	Sources: https://clinicaltrials.gov/ct2/show/NCT02394340

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2B6 810 CYP2C8 911		CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204153s004s005lbl.pdf#page=5 Page: 5.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204153s004s005lbl.pdf#page=5 Page: 5.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204153s004s005lbl.pdf#page=5 Page: 5.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	yes [Ki 0.13 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204153s004s005lbl.pdf#page=5 Page: 5.0	yes
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204153s004s005lbl.pdf#page=5 Page: 5.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	major
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000ClinPharmR.pdf#page=6 Page: 6.0	major

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204153Orig1s000PharmR.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA003RAX	https://www.aablocks.com/goods/Goods/detail?id=AA003RAX
Aaron Chemicals	AR003S2P	http://www.aaronchem.com/187164-19-8
AbMole Bioscience	M3182	http://www.abmole.com/products/luliconazole.html
Achemo Scientific Limited	AC-65105	http://www.achemo.com/search/?Keyword= 187164-19-8
Achemtek	0102-012960	http://www.achemtek.com/187164-19-8
Acorn PharmaTech	ACN-036087	http://www.acornpharmatech.com/
Adooq BioScience	A11481	https://www.adooq.com/luliconazole.html
Alfa Chemistry	AP187164198	https://reagents.alfa-chemistry.com/product/luliconazole-cas-187164-19-8-6957.html
Alsachim	4170	http://www.alsachim.com/product-C5486-glo.bal-view.html
Ansion Pharma	187164-19-8	http://www.ansionpharma.com/English/Product/4235191430.html
Aurum Pharmatech LLC	W-5249	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5249
BLD Pharm	BD136847	http://www.bldpharm.com/products/187164-19-8.html
BioCrick	BCC1711	http://www.biocrick.com/Luliconazole-BCC1711.html
CSNpharm	CSN11342	https://www.csnpharm.com/products/luliconazole.html
Chem Scene	CS-0587	http://www.chemscene.com/187164-19-8.html
ChemMol	49408861	http://www.chemmol.com/chemmol/49408861.html
Chemspace	CSSB00020642397	https://chem-space.com/CSSB00020642397
Glentham Life Sciences	GP4563	http://www.glentham.com/products/product/GP4563/
Lab Network	LN01289958	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01289958
MedChem Express	HY-14283	https://www.medchemexpress.com/Luliconazole.html
OChem	25408	http://www.ocheminc.com/index.php?act=psearch&pid=164L198
Parchem	29325	http://www.parchem.com/chemical-supplier-distributor/Luliconazole-019325.aspx
Sigma-Aldrich	SML1595_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml1595?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S061076	http://www.sinfoobiotech.com/product/1064479
Synblock Inc	SB18987	http://www.synblock.com/product/187164-19-8.html
Yuhao Chemical	HL3762	http://www.chemyuhao.com/187164-19-8.html
abcr GmbH	AB480096	http://www.abcr.com/shop/en/AB480096
iChemical	EBD5761	http://www.ichemical.com/chemicals/cas-187164-19-8

PubMed

Title	Date	PubMed
Efficacy of NND-502, a novel imidazole antimycotic agent, in experimental models of Candida albicans and Aspergillus fumigatus infections.	1999 Aug	10461840

Patents

Sample Use Guides

In Vivo Use Guide

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:37:31 GMT 2023` Edited by `admin` on `Fri Dec 15 17:37:31 GMT 2023`
Record UNII	RE91AN4S8G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LULICONAZOLE

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