Liranaftate

Base Information

• Chemical Name: Liranaftate
• CAS No.: 88678-31-3
• Molecular Formula: C₁₈H₂₀N₂O₂S
• Molecular Weight: 328.435
• European Community (EC) Number: 834-254-6
• UNII: 5253IGO5X3
• DSSTox Substance ID: DTXSID6046470
• Nikkaji Number: J402.975E
• Wikipedia: Liranaftate
• Wikidata: Q27167100
• NCI Thesaurus Code: C66019
• ChEMBL ID: CHEMBL1591365
• Mol file: 88678-31-3.mol

Synonyms:liranaftate;O-(5,6,7,8-tetrahydro-2-naphthyl)-6-methoxy-N-methylthio-2-pyridinecarbamate

Chemical Property of Liranaftate

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 9.84E-09mmHg at 25°C
• Melting Point: 98.5-99.5 °C
• Refractive Index: 1.641
• Boiling Point: 462.5 °C at 760 mmHg
• PKA: 1.24±0.10(Predicted)
• Flash Point: 233.5 °C
• PSA: 66.68000
• Density: 1.24 g/cm³
• LogP: 3.76910
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 328.12454906
• Heavy Atom Count: 23
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Liranafate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1=NC(=CC=C1)OC)C(=S)OC2=CC3=C(CCCC3)C=C2
• Description: Liranaftate was launched in Japan as a new topical antifungal for the treatment of dermatophycoses. This compound belonging to the thiocarbamate class of antifungals can be prepared by condensation of 5,6，7,8-tetrahydro-2-naphthol with the corresponding Npyridylthiocarbamoyl chloride. It is a potent and specific inhibitor of squalene epoxidase and consequently a blocker of ergosterol biosynthesis in fungi, without any detectable effect on mammalian cholesterol biosynthesis in rat liver at therapeutic dose levels. Liranaftate was found to be significantly more active than the other thiocarbamate tolnaftate against several dermatophytes, including Trichophyton mentagrophyfes, and against certain yeasts, such as Crypfococcus neoformans. On the other hand, it was inactive against a variety of Gram-positive and negative bacteria. When applicated as a 1 or 2% cream during clinical trials, it was well tolerated and no systemic absorption was observed.
• Uses: A squalene epoxidase inhibitor. Used as an antifungal. A squalene epoxidase inhibitor. Used as an antifungal

Technology Process of Liranaftate

There total 2 articles about Liranaftate 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: 58.0%

5,6,7,8-Tetrahydro-2-naphthol (1125-78-6) + sodium 6-methoxy-2-methylaminopyridine dithiocarbamate + 1,1-dibromomethane (74-95-3) → liranaftate (88678-31-3)

Guidance literature:

With sodium hydroxide; In ethyl acetate; N,N-dimethyl-formamide;

Reference yield: 58.0%

6-methoxy-2-methylaminopyridinedithiocarbamic acid sodium salt → liranaftate (88678-31-3)

Guidance literature:

5,6,7,8-Tetrahydro-2-naphthol; With sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

6-methoxy-2-methylaminopyridinedithiocarbamic acid sodium salt; With 1,1-dibromomethane; In N,N-dimethyl-formamide; at 10 - 20 ℃; for 1.25h; Product distribution / selectivity;

upstream raw materials:

5,6,7,8-Tetrahydro-2-naphthol

1,1-dibromomethane

Refernces

• 1、 -. "METHOD FOR PRODUCING THIOCARBAMATE DERIVATIVE". Page/Page column 7. . Retrieved 2008/06/13.