Luliconazole

Base Information

• Chemical Name: Luliconazole
• CAS No.: 187164-19-8
• Molecular Formula: C₁₄H₉Cl₂N₃S₂
• Molecular Weight: 354.284
• European Community (EC) Number: 878-713-9
• UNII: RE91AN4S8G
• DSSTox Substance ID: DTXSID3048607
• Nikkaji Number: J937.034J
• Wikipedia: Luliconazole
• Wikidata: Q15624030
• NCI Thesaurus Code: C81510
• RXCUI: 1482680
• Metabolomics Workbench ID: 70059
• ChEMBL ID: CHEMBL2105689
• Mol file: 187164-19-8.mol

Synonyms:(2E)-((4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)(1H-imidazol-1-yl)acetonitrile;4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile;Lulicon;luliconazole;NND 502;NND-502;NND502

Chemical Property of Luliconazole

Chemical Property:

• Vapor Pressure: 4.27E-10mmHg at 25°C
• Melting Point: 152 °C
• Refractive Index: 1.734
• Boiling Point: 499.102 °C at 760 mmHg
• PKA: 3.76±0.10(Predicted)
• Flash Point: 255.648 °C
• PSA: 92.21000
• Density: 1.524 g/cm³
• LogP: 5.06088
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.9614950
• Heavy Atom Count: 21
• Complexity: 476

Purity/Quality:

99% ^*data from raw suppliers

Luliconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl
• Isomeric SMILES: C1[C@H](S/C(=C(\C#N)/N2C=CN=C2)/S1)C3=C(C=C(C=C3)Cl)Cl
• Recent ClinicalTrials: Multicenter Study of the Efficacy and Safety of Luliconazole Cream in Tinea Pedis (Athlete's Foot)
• Uses: It can be used for the following fungal infections: Ringworm: athlete's foot, ringworm, jock itch; Candida infections: disease fingers erosion, intertrigo; vitiligo. Luliconazole 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.
• 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. .

Technology Process of Luliconazole

There total 38 articles about Luliconazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate → (-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile (256424-63-2,187164-19-8)

Guidance literature:

With water; sodium hydroxide; at 40 ℃; for 0.333333h;

Reference yield: 91.0%

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate (229334-55-8) + C6H3N3S2(2-)*2K(1+) → luliconazole (187164-19-8)

Guidance literature:

With potassium hydroxide; In acetonitrile; at -10 - 10 ℃; for 1h; Large scale;

Reference yield: 91.0%

(E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile toluenesulfonate → luliconazole (187164-19-8)

Guidance literature:

With water; sodium hydroxide; at 40 ℃; for 0.333333h;

upstream raw materials:

carbon disulfide

1-cyanomethylimidazole

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

2,4-dichlorophenacyl bromide

Refernces

• 1、 -. "Production methods of luliconazole and hydrochloride thereof". Paragraph 0118-0119; 0124-0160. . Retrieved 2021/10/27.
• 2、 Wei, Teng-Yun,Tang, Jia-Wei,Ni, Guo-Wei,Wang, Hong-Yi,Yi, Dong,Zhang, Fu-Li,Chen, Shao-Xin. "Development of an Enzymatic Process for the Synthesis of (S)-2-Chloro-1-(2,4-dichlorophenyl) Ethanol". . p. 1822 - 1828. Retrieved 2019/09/30.