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Luliconazole

CAS NO.187164-19-8

  • Min.Order: 1 Kilogram
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Product Details

Keywords

  • (2E)-2-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile
  • 4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile
  • C13478

Quick Details

  • ProName: Luliconazole
  • CasNo: 187164-19-8
  • Molecular Formula: C14H9Cl2N3S2
  • Appearance: White powder
  • Application: Pharmaceutical raw materials
  • DeliveryTime: within 7-10days
  • PackAge: as required
  • Port: TIANJIN/SHANGHAI
  • ProductionCapacity: 100 Kilogram/Month
  • Purity: 98%
  • Storage: room temperature
  • Transportation: by air/ by sea/ by express
  • LimitNum: 1 Kilogram

Superiority

Luliconazole Basic information
Outline Synthetic method Application Ringworm Pharmacodynamics
Product Name: Luliconazole
Synonyms: Luliconazole;(2E)-2-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile;4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile;C13478;Lulicon;NND 502;1H-Imidazole-1-acetonitrile,a-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-,(aE)-
CAS: 187164-19-8
MF: C14H9Cl2N3S2
MW: 354.28
EINECS:  
Product Categories: APIs;Inhibitors
Mol File: 187164-19-8.mol
Luliconazole Structure
 
Luliconazole Chemical Properties
 
Safety Information
MSDS Information
 
 
Luliconazole Usage And Synthesis
Outline Luliconazole is a novel topical antifungal imidazole, and is a kind of analogue of lanoconazole. It can interfere with the fungal cell wall synthesis and fungal growth by decreasing levels of ergosterol via inhibiting lanosterol demethylase activity. Besides being used for the treatment of athlete's foot, jock itch and ringworm, it has also been developed for onychomycosis (nail fungus) treatment and has now also entered the clinical stage phase III. This product was originally developed by the Japanese pesticide Corporation (NihonNohyaku Co., Ltd.). In November 2013, the FDA has approved a 1% luliconazole cream for entering into market for topical treatment of interdigital athlete's foot, jock itch and ringworm with the trade name being Luzu and first entered into market in North America. As early as April 2005, luliconazole had been approved to enter into market in Japan under the trade name Lulicon. In January 2010 and June 2012, it was approved for marketing in India and China, respectively. 
In 1997, Pesticide Co., Ltd. of Japan has initially get access to the worldwide patent of luliconazole as antifungal agents (WO 1997002821 A2) and have protected in their preparation and application; thereafter, it had also applied for a European patent (EP0839035 A2), Chinese patent (CN 1194582 A) and U.S. Patent (US5900488A). In addition, WO 2007102241, US 8058303, and other patents have also been applied for protection on the drug's pharmaceutical compositions and dosage forms.
Synthetic method The first method is using BH3/THF and a kind of chiral catalyst for stereoselectively reducing the starting material 1 to give the intermediate 2 which yields the corresponding mesylate intermediate (3), substance 3 and intermediate 5 is cyclized into luliconazole in the presence of potassium hydroxide and DMSO; second method is based on using chiral compound 6 as starting materials, 6 undergoes mesylate esterification to yield active intermediate 7,7 undergoes condensation reaction with intermediate 5 to get luliconazole. The synthesis of Intermediate 5 is through putting 2- (1-imidazolyl) - acetonitrile and CS2 into condensation under basic conditions.
synthesis route of luliconazole
Figure 1 is a synthesis route of luliconazole
Application It can be used for the following fungal infections: 
Ringworm: athlete's foot, ringworm, jock itch; 
Candida infections: disease fingers erosion, intertrigo; vitiligo.
Ringworm Currently, ringworm treatment drugs include two major categories: first, propylene amine drugs, such as terbinafine, Butenafine and naftifine. They exert their bactericidal effects through inhibiting squalene cyclase, causing the lack of ergosterol and accumulation of squalene. The second category of imidazole (imidazoles) drugs: such as miconazole, econazole, clotrimazole, ketoconazole and bifonazole. They are a class of synthetic antifungal agent that can selectively inhibit the lanosterol 14α- demethylation activity of fungal cell, preventing the ergosterol synthesis of cell membrane, changing the cell membrane permeability, and resulting in the loss of important intracellular fungal material and causing fungal death. Imidazole antifungal agents are currently the most commonly used drugs in clinical treatment of ringworm with extensive clinical applications.
Pharmacodynamics In vitro and in vivo studies have shown that luliconazole has broad-spectrum antifungal activity, with its minimum inhibitory concentration (MIC) being 0.12 to 2 mg/mL to Trichophyton (Trichophyton rubrum, Trichophyton mentagrophytes and tonsurans). Its anti-fungal effect is stronger than terbinafine, ketoconazole, miconazole, bifonazole and other commonly used drugs. Trichophyton rubrum is most sensitive to luliconazole. The MIC of Luliconazole to Candida albicans is 0.031 ~ 0.130μg / mL with the inhibitory effect being higher than that of terbinafine, Liranaftate, Butenafine, amorolfine and bifonazole, but less than that of ketoconazole, clotrimazole, neticonazole and miconazole. The MIC of Luliconazole on the important pathogens of seborrheic dermatitis, limiting Malassezia is very low, being 0.004 ~ 0.016 μg / mL with its inhibitory effect being not less but even stronger than ketoconazole. 
In addition, luliconazole also have antifungal activity on filamentous fungi and yeast-like fungi with its strength being comparable as lanoconazole but higher than bifonazole and terbinafine, but being almost ineffective on Zygomycetes.
The above information is edited by the chemicalbook of Dai Xiongfeng.

 

Details

Product information

 

synthesis route of luliconazole

 1)Basic information
Outline Synthetic method Application Ringworm Pharmacodynamics
Product Name: Luliconazole
Synonyms: Luliconazole;(2E)-2-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile;4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile;C13478;Lulicon;NND 502;1H-Imidazole-1-acetonitrile,a-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-,(aE)-
CAS: 187164-19-8
MF: C14H9Cl2N3S2
MW: 354.28
EINECS:  
Product Categories: APIs;Inhibitors
Mol File: 187164-19-8.mol
Luliconazole Structure

2)Usage And Synthesis
It can be used for the following fungal infections: 
Ringworm: athlete's foot, ringworm, jock itch; 
Candida infections: disease fingers erosion, intertrigo; vitiligo.

Company information

 Henan sunlake enterprise corporation is located in Henan Province , The central plain of China , Which enjoys favorable geogeaphical position and convenient transportion, The com[any was established in june. 1998 , until now having more than 18 years experience in manufacturing & exporting chemical raw material .

     Sunlake is a professional manufacturer engaged in producing and selling chemicals,including Organic & inorganic chemicals , pigments & Dyestuffs ,  Water treatment chemicals , Food & FEED additives and others . these products have been being well exported to europe , southeast Asia , the Middle East ,  Africa , South America and some other countries and areas.

    We sincerely welcome foreign friends to visit our plant for cooperation. With the idea of "quality first,credit priority, Excellent service", We are highly acknowledged by customers for good quality and competitive price. More importantly , the company has a strong R & D team, who are professional engineers and scholars with Ph. D. .So we are confident to serve you  better with our high - quality products and professional team.

    We are taking great efforts to provide our customers with demanded goods and professional services, and continuously improve our core ability of competition and get the momentum for sustainable development, and finally make us being a reliable and professional wupplier in international market.

    We  welcome any serious inquiries from all customers of the world, and sincerely hope to cooperate.

 

 

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