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Luliconazole

Outline Synthetic method Uses Ringworm Pharmacodynamics
Luliconazole
Luliconazole structure
CAS No.
187164-19-8
Chemical Name:
Luliconazole
Synonyms
C13478;NND 502;Lulicon;Luliconazole;NND 502; LULICON;Luliconazole fandachem;Luliconazole USP/EP/BP;Luliconazole (NND 502);(R)-Luliconazole E-isomer;Luliconazole (This product is only available in Japan.)
CBNumber:
CB01120404
Molecular Formula:
C14H9Cl2N3S2
Formula Weight:
354.27
MOL File:
187164-19-8.mol

Luliconazole Properties

Melting point:
152 °C
Boiling point:
499.1±55.0 °C(Predicted)
Density 
1.52±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
pka
3.76±0.10(Predicted)
CAS DataBase Reference
187164-19-8
FDA UNII
RE91AN4S8G
ATC code
D01AC18

Luliconazole price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical L0306 Luliconazole >98.0%(HPLC)(N) 187164-19-8 250mg $49 2021-12-16 Buy
TCI Chemical L0306 Luliconazole >98.0%(HPLC)(N) 187164-19-8 1g $133 2021-12-16 Buy
Cayman Chemical 23120 Luliconazole ≥98% 187164-19-8 500mg $124 2021-12-16 Buy
Cayman Chemical 23120 Luliconazole ≥98% 187164-19-8 250mg $69 2021-12-16 Buy
TRC L473770 Luliconazole 187164-19-8 250mg $105 2021-12-16 Buy

Luliconazole Chemical Properties,Uses,Production

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

Uses

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.

Description

Luliconazole 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. .

Originator

Nihon Nohyaku (Japan)

Uses

Luliconazole is an azole antifungal drug.

brand name

Lulicon

Chemical Synthesis

Synthesis of luliconazole started with diol 77, prepared according to literature procedure in 98%ee which was activated by converting to dimesylate 78 in 99% yield and coupled to dipotassium enolate 80, prepared in situ by reacting cyano methylimidazole 79 with carbon disulfide, to give luliconazole (XI), 99% ee in 48% yield.

Luliconazole Preparation Products And Raw materials

Raw materials

Preparation Products


Luliconazole Suppliers

Global( 203)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
Shenzhen Shengda Pharma Limited
+86-755-85269922
WeChat:shengdapharm sales@shengdapharm.com CHINA 309 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 9107 55
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29954 58
TianYuan Pharmaceutical CO.,LTD
+86-755-23284190 13684996853
+86-755-23284190 sales@tianpharm.com CHINA 305 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
hdzhl biotechnology co., ltd
86-13032617415
sales@luchibiology.com CHINA 1275 58

View Lastest Price from Luliconazole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-30 Luliconazole
187164-19-8
US $2320.00 / KG 1KG 98% 1-500kg Baoji Guokang Bio-Technology Co., Ltd.
2021-11-15 Luliconazole
187164-19-8
US $0.00 / KG 1KG 98% 200000pcs Hebei Yirun Sega Biological Technology Co. Ltd
2021-07-17 Luliconazole USP/EP/BP
187164-19-8
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited

187164-19-8(Luliconazole)Related Search:


  • 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)-
  • Luliconazole (This product is only available in Japan.)
  • (R,E)-2-(4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE)-2-(1H-IMIDAZOL-1-YL)ACETONITRILE
  • NND 502; LULICON
  • (αE)-α-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-1H-imidazole-1-acetonitrile
  • (R)-Luliconazole E-isomer
  • 1H-Imidazole-1-acetonitrile, α-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-, (αE)-
  • Luliconazole fandachem
  • (2E)-2-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile
  • Luliconazole USP/EP/BP
  • Luliconazole (NND 502)
  • 187164-19-8
  • 87164-19-8
  • intermediate
  • APIs
  • Inhibitors
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