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Luliconazole

HCID 3003141
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
187164-19-8
Standard SMILES
N#C/C(=C1/SC[C@@H](c2ccc(Cl)cc2Cl)S1)n1ccnc1
InChIKey
YTAOBBFIOAEMLL-REQDGWNSSA-N
Molecular formula
C14H9Cl2N3S2
Average molar mass
354.287 g/mol
Monoisotopic mass
352.96149465

Names & identifiers

Preferred name
Luliconazole
IUPAC
(2E)-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)acetonitrile
English name
Luliconazole
Molecular formula
C14H9Cl2N3S2
Molecular weight
354.27

Names & synonyms

(R,E)-2-(4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE)-2-(1H-IMIDAZOL-1-YL)ACETONITRILEC13478PR2699NND 502LuliconPR 2699PR-2699LuliconazoleLuriconazoleLulioconazole

Database identifiers

CAS
187164-19-8
PubChem CID
3003141
DTXSID
DTXSID3048607
ChEMBL
CHEMBL2105689
ChEBI
CHEBI:34825
UNII
RE91AN4S8G
EC Number
878-713-9
Nikkaji
J937.034J

Properties

Physicochemical properties

Melting point
152 °C · 152 °C
Boiling point
499.1 · 499.1±55.0 °C(Predicted)
Density
1.52 · 1.52±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Solid
pka
3.76 · 3.76±0.10(Predicted)
color
White to Off-White
Stability
Light Sensitive
InChI
InChI=1/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-/s3
InChIKey
YTAOBBFIOAEMLL-YZDXEGGZNA-N
SMILES
ClC1C=C(Cl)C=CC=1[C@@H]1CS/C(=C(\N2C=NC=C2)/C#N)/S1 |&1:8,r|
CAS DataBase Reference
187164 · 187164-19-8
FDA UNII
91 AN4S8G · RE91AN4S8G
ATC code
1 AC18 · D01AC18
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H319-H315
Precautionary statements
264 · P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
WGK Germany
3 · WGK 3
HS Code
2933.29 · 2933.29.2000

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
2933.29.2000
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302-H319-H315
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2
Precautionary statements
P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 3 items

UsesIt can be used for the following fungal infections: Ringworm: athlete's foot, ringworm, jock itch; Candida infections: disease fingers erosion, intertrigo; vitiligo.

DescriptionLuliconazole is a member of the imidazole class of antifungal agents, with specific utility as a dermatological antimycotic drug. It was launched in Japan as a topical agent for the treatment of athlete’s foot. Luliconazole is an optically active drug with (R)-configuration at its chiral center. It is structurally related to lanoconazole, which has been marketed as a racemic mixture since 1994. As with other azole antifungal drugs, the mechanism of action of luliconazole is the inhibition of sterol 14-a-demethylase, and subsequently, inhibition of ergosterol biosynthesis. The in vivo activity of luliconazole against dermatophytes has been evaluated in the guinea pig model of tinea pedis. In this study, a 1% topical solution of luliconazole, administered once daily for seven days, achieved complete mycologic cure. Additionally, there were no occurrences of relapse for up to 16 weeks after the treatment. No data is currently available on the clinical efficacy of luliconazole. The chemical synthesis of luliconazole involves the condensation of 1-(cyanomethyl)imidazole with carbon disulfide to produce a dithioate intermediate, and subsequent alkylation with either the mesylate derivative of (S′)-1-(2,4-dichlorophenyl)-2-bromoethanol or the bis-mesylate derivative of (S′)-1-(2,4-dichlorophenyl)ethane-1,2-diol. .

UsesLuliconazole is an azole antifungal drug. It was approved by the FDA (USA) in November 2013 and is marketed under the brand name Luzu. Luliconazole is also approved in Japan.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
常州康特医药技术有限公司0519-82813797 18994752886 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
上海贝美医药科技有限公司21-33738120 15000110506 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
上海迪外化工科技有限公司021-61551100
上海源叶生物科技有限公司18916372613 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
泰州同新生物医药科技有限公司0523-86818997 18652728585 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
南京伶亚生物医药科技有限公司18068075658 · [email protected]
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
成都赛诺宁科技有限公司28-87999436 02887999436 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
上海必联特生物医药科技有限公司021-20786057 18918495077 · [email protected]

Additional notes

DefinitionChEBI: Luliconazole is a dichlorobenzene.