4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile
Luliconazole
CAS: 187164-19-8
Molecular Formula: C14H9Cl2N3S2
4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile - Names and Identifiers
| Name | Luliconazole |
| Synonyms | C13478 Lulicon NND 502 Luliconazole Luliconazole (This product is only available in Japan.) 4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile (2E)-2-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile (2E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)ethanenitrile 1H-Imidazole-1-acetonitrile,a-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-,(aE)- |
| CAS | 187164-19-8 |
| EINECS | 247-960-9 |
| 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-/m0/s1 |
4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile - Physico-chemical Properties
| Molecular Formula | C14H9Cl2N3S2 |
| Molar Mass | 354.27 |
| Density | 1.52±0.1 g/cm3(Predicted) |
| Melting Point | 152 °C |
| Boling Point | 499.1±55.0 °C(Predicted) |
| Flash Point | 255.6°C |
| Solubility | DMSO 71 mg/mL (200.4 mM);Water <1 mg/mL (<1 mM);Ethanol 5 mg/mL (14.11 mM) |
| Vapor Presure | 4.27E-10mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 3.76±0.10(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Stability | Light Sensitive |
| Refractive Index | 1.734 |
| In vitro study | Low concentrations of Luliconazole inhibited all filamentous fungi except Zygomycetes (MIC,≦ 0.004-0.125 micrograms/ml), dermatophytosis is the most sensitive (MIC,≦ 0.004-0.008 micrograms/ml). Compared with the control drug, Luliconazole showed greater efficacy against Trichophyton (MIC,≦ 0.00012-0.002 mg/mL), and Trichophyton rubrum was the most sensitive. Luliconazole also had high activity against Candida albicans (MIC range: 0.031-0.13 mg/mL), proved to be more effective than terbinafine, riranaphate, butenafine, amoroxene, bifonazole and, but less effective than ketoconazole, clotrimazole, neticonazole and miconazole. |
| In vivo study | In the guinea pig model with beriberi, the clinical effect of Luliconazole(1% cream) treatment was slightly lower than that of terbinafine. Luliconazole(1% cream) treated guinea pigs with hair covered with amorphous debris and a small number of conidia were detected. Luliconazole has improved potency over Lanoconazole, probably because Luliconazole is a strict R-enantiomer whereas Lanoconazole is a racemic mixture. |
4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile - Introduction
Luliconazole is a broad-spectrum antifungal drug.
Last Update：2022-10-16 17:14:36
4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile - Reference Information
| Overview | Luliconazole is a new type of imidazole topical antifungal drug. It is a lanoconazole analog. It inhibits the activity of lanosterol demethylase and reduces the level of ergosterol to interfere with the synthesis of fungal cell walls and the growth of fungi. In addition to the treatment of tinea pedis, tinea cruris and tinea corporis, it has also been developed for the treatment of onychomycosis (onychomycosis) and has now entered phase III clinical practice. This product was originally developed by Japan pesticide co., ltd. (NihonNohyaku co., ltd.). In November 2013, the US FDA approved 1% luliconazole cream for external use to treat tinea pedis, tinea cruris and tinea corporis, under the trade name Luzu, which was first listed in North America. As early as April 2005, luliconazole was approved for listing in Japan under the trade name Lulicon. In January 2010 and June 2012, they were listed in India and China respectively. Japan Pesticide Co., Ltd. won the world patent of luliconazole as an antifungal agent (WO 1997002821 A2) in 1997, and protected its preparation method and application. Since then, it has also applied for European patents (EP0839035 A2), Chinese patents (CN 1194582 A) and U.S. patents (US5900488A). In addition, WO 2007102241, US 8058303 and other patents have also applied for protection of the pharmaceutical composition and dosage form of the drug. |
| Synthesis method | The first method uses BH3/THF and a chiral catalyst to stereoselectively reduce starter 1 to obtain intermediate 2, intermediate 2 under the action of MsCl and TEA to generate the corresponding mesylate 3,3 and intermediate 5 under the conditions of potassium hydroxide and DMSO to obtain luliconazole; the second method is to use the chiral raw material 6 as the starting material, 6 is sulfonated to obtain the active intermediate 7,7 is condensed with the intermediate 5 to obtain luliconazole. The synthesis of intermediate 5 is obtained by condensation of 2-(1-imidazolyl)-acetonitrile and CS2 under basic conditions. Fig. 1 shows the synthesis route of luliconazole |
| use | for the following fungal infections: ringworm: athlete's foot, tinea corporis, tinea cruris; Candida infection: interphalangeal erosion, wiping; purpura wind. |
| ringworm | at present, there are two main types of ringworm treatment drugs: the first type of propylamine drugs, such as terbinafine, butenafine and naftifine. They are antifungal drugs that inhibit squalene cyclase, causing ergosterol deficiency and squalene accumulation, thereby playing a bactericidal effect. The second class of imidazole (imidazoles) drugs, such as miconazole, econazole, clotrimazole, ketoconazole and bifonazole. They are a class of synthetic antifungal drugs, which can selectively inhibit the activity of lanosterol 14 α-demethylase in fungal cells, prevent the synthesis of ergosterol in cell membranes, change the permeability of cell membranes, and cause the loss of important intracellular substances. Death of fungi. Imidazole antifungal drugs are currently the most commonly used drugs for the treatment of ringworm diseases and are widely used in clinical practice. |
| pharmacodynamics | in vitro and in vivo studies show that luliconazole has broad-spectrum antifungal activity, and its minimum inhibitory concentration (MIC) against Trichophyton (Trichophyton rubrum, Trichophyton trichophyton and Trichophyton trichophyton) is 0.12~2 mg/mL, and its antibacterial effect is stronger than that of terbinafine, ketoconazole, miconazole, bifonazole and other commonly used drugs, among them, Trichophyton rubrum is the most sensitive to luliconazole. The MIC of luliconazole to Candida albicans was 0.031~0.130 μg/mL, and its antibacterial effect was higher than that of terbinafine, liranate, butenafine, amoprofen and bifonazole, but lower than that of ketoconazole, clotrimazole, neconazole and miconazole. The MIC of luliconazole to Malassezia, an important pathogen of seborrheic dermatitis, is also very low, 0.004~0.016 μg/mL, and its antibacterial effect is not lower than ketoconazole, or even stronger. In addition, luliconazole also has antibacterial activity against filamentous fungi and yeast-like fungi, and its strength is similar to that of Ranoconazole, which is higher than that of bifonazole and terbinafine, but it is almost ineffective against conjugate bacteria. (2016-01-13) |
| biological activity | Luliconazole is a broad-spectrum antifungal drug. |
Last Update：2024-04-09 21:50:46
Supplier List
Spot supply
Product Name: Luliconazole Visit Supplier Webpage Request for quotationCAS: 187164-19-8
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Luliconazole Visit Supplier Webpage Request for quotationCAS: 187164-19-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Luliconazole Visit Supplier Webpage Request for quotationCAS: 187164-19-8
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Luliconazole Visit Supplier Webpage Request for quotationCAS: 187164-19-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History