Tolnaftate

Base Information

• Chemical Name: Tolnaftate
• CAS No.: 2398-96-1
• Deprecated CAS: 94256-64-1
• Molecular Formula: C19H17NOS
• Molecular Weight: 307.416
• Hs Code.: 2930206050
• European Community (EC) Number: 219-266-6
• NSC Number: 757355,233648
• UNII: 06KB629TKV
• DSSTox Substance ID: DTXSID3042477
• Nikkaji Number: J4.423G
• Wikipedia: Tolnaftate
• Wikidata: Q415238
• NCI Thesaurus Code: C47763
• RXCUI: 10637
• Pharos Ligand ID: W17T82Y8JL47
• Metabolomics Workbench ID: 38694
• ChEMBL ID: CHEMBL83668
• Mol file: 2398-96-1.mol

Synonyms:Aftate;Breezee;Chinofungin;Chlorisept;Curatin;Genaspor;Micoisdin;NP 27;NP-27;NP27;Ony Clear;Ony-Clear;Purder N, Tolnaftat;Sporiline;Tinactin;Tinaderm;Tinatox;Tineafax;Ting;Tolnaftat Purder N;Tolnaftate;Tonoftal;ZeaSorb

Chemical Property of Tolnaftate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.08E-08mmHg at 25°C
• Melting Point: 110.5-111.5°C
• Refractive Index: 480 C
• Boiling Point: 453.4 °C at 760 mmHg
• PKA: -0.35±0.50(Predicted)
• Flash Point: 228 °C
• PSA: 44.56000
• Density: 1.223 g/cm³
• LogP: 4.94830
• Storage Temp.: 2-8°C
• Solubility.: Soluble in chloroform at 50 mg/ml. Sparingly soluble in ethanol
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 307.10308534
• Heavy Atom Count: 22
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

Tolnaftate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)N(C)C(=S)OC2=CC3=CC=CC=C3C=C2
• Recent ClinicalTrials: Effectiveness of Polymyxin B Sulphate + Prednisolone + Benzocaine + Clioquinol in Acute and Sub-acute Dermatitis Eczematous
• Description: Tolnaftate is a thiocarbamate antifungal agent. It is active against clinical isolates of the dermatophytes T. rubrum, T. mentagraphytes, T. verrucosum, E. floccosum, and M. canis (MIC50s = 50, 100, 6, 50, and 50 ng/ml, respectively), as well as 18 additional yeast and filamentous fungi species (MIC = 0.003-0.8 μg/ml)., Tolnaftate also reduces aflatoxin production in A. parasiticus in a concentration-dependent manner. It inhibits squalene epoxidase with an IC50 value of 12.5 μg/ml in a cell-free assay.
• Uses: Tolnaftate is used to study the mechanism of ergosterol (sterol) biosynthesis at the rate-limiting step of squalene epoxidase inhibition. Tolnaftate is clinically used to treat cutaneous infections such as athlete?s foot, jock itch, and ringworm1. It also has been used as a comparator compound for antifungal efficiency studies. antifungal for cutaneous infections. Tolnaftate (Aftate, Tinactin, etc.) is an odorless and nonstaining synthetic antifungal agent whose exact mechanism of action is unknown. It is effective against dermatophytes and P. orbiculare and Pityrosporum ovale. It is ineffective against C. albicans and bacteria. Tolnaftate topical is used to treat skin infections such as athlete's foot, jock itch, and ringworm infections. Tolnaftate is also used, along with other antifungals, to treat infections of the nails, scalp, palms, and soles of the feet.
• Indications: Tolnaftate (Aftate, Tinactin, etc.) is an odorless and nonstaining synthetic antifungal agent whose exact mechanism of action is unknown. It is effective against dermatophytes and P. orbiculare and Pityrosporum ovale. It is ineffective against C. albicans and bacteria.
• Therapeutic Function: Antifungal
• Clinical Use: O,2-Naphthyl m,N-dimethylthiocarbanilate (Tinactin,Aftate, NP-27) is a white crystalline solid that is insoluble inwater, sparingly soluble in alcohol, and soluble in most organicsolvents. The compound, a thioester of β-naphthol, isfungicidal against dermatophytes, such as Trichophyton,Microsporum, and Epidermophyton spp., that cause superficialtinea infections. Tolnaftate is available in a concentrationof 1% in creams, powders, aerosols, gels, and solutionsfor the treatment of ringworm, jock itch, and athlete’s foot.Tolnaftate has been shown to act as an inhibitor of squaleneepoxidase in susceptible fungi, so it is classified with theallylamine antimycotics. Tolnaftate is formulated into preparationsintended to be used with artificial fingernails to counteractthe increased chance of ringworm of the nail beds. Tolnaftate (Tinactin, others) is a nonprescription antifungal agent effective in the topical treatment of dermatophyte infections and tinea. The mechanism of action is unknown.

Technology Process of Tolnaftate

There total 4 articles about Tolnaftate 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:

N-methyl-N-(3-methylphenyl)thioformyl chloride (36592-58-2) + β-naphthol (135-19-3) → tolnaftate (2398-96-1,94256-64-1)

Guidance literature:

With tetrabutylammomium bromide; sodium carbonate; In toluene; for 5h; Reflux;

Reference yield:

N-methyl-N-(3-methylphenyl)carboxamide (39970-42-8) → tolnaftate (2398-96-1,94256-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetraphosphorus decasulfide / toluene / Reflux

2: thionyl chloride / toluene / 2 h / Reflux

3: tetrabutylammomium bromide; sodium carbonate / toluene / 5 h / Reflux

With thionyl chloride; tetraphosphorus decasulfide; tetrabutylammomium bromide; sodium carbonate; In toluene;

Reference yield:

N-methyl-m-toluidine (696-44-6) → tolnaftate (2398-96-1,94256-64-1)

Guidance literature:

Multi-step reaction with 4 steps

1: zinc / 40 °C / Reflux

2: tetraphosphorus decasulfide / toluene / Reflux

3: thionyl chloride / toluene / 2 h / Reflux

4: tetrabutylammomium bromide; sodium carbonate / toluene / 5 h / Reflux

With thionyl chloride; tetraphosphorus decasulfide; tetrabutylammomium bromide; sodium carbonate; zinc; In toluene;

upstream raw materials:

N-methyl-N-(3-methylphenyl)carboxamide

N-methyl-m-toluidine

N-methyl-N-(3-methylphenyl)thioformyl chloride

β-naphthol

Downstream raw materials:

hydrogen sulfide

β-naphthol

Methyl-m-tolyl-carbamic acid naphthalen-2-yl ester

Refernces

• 1、 -. "A N-methyl-N-(3-methyl phenyl) dithio-2-clamping the method for the preparation of". . . Retrieved 2017/05/26.