2398-96-1 Usage
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.
Chemical Properties
White Solid
Originator
Tinactin,Schering,US,1965
Uses
Different sources of media describe the Uses of 2398-96-1 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
Definition
ChEBI: A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.
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.
Manufacturing Process
In a first step, 2-naphthol is reacted with thiophosgene to give 2-naphthyl
chlorothionoformate.
A mixture of 4.0 grams of N-methyl-3-toluidine and 2.8 grams of sodium
hydrogencarbonate in 50 cc of acetone was stirred at 0° to 10°C and 7.4 grams of 2-naphthyl chlorothionoformate was added in small portions thereto
and the mixture was heated under reflux for 30 minutes. The cooled mixture
was poured into about 150 cc of cold water and 2-naphthyl-N-methyl-N-(3-
tolyl)thionocarbamate was obtained as white crystals. Yield is 9.1 grams
(90%). Recrystallization from alcohol gave colorless needle crystals, MP
110.5° to 111.5°C.
Therapeutic Function
Antifungal
General Description
Crystals or white powder.
Reactivity Profile
Tolnaftate is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Health Hazard
SYMPTOMS: In susceptible persons, Tolnaftate may cause sensitization or irritation.
Fire Hazard
Flash point data on Tolnaftate are not available, Tolnaftate is probably combustible.
Clinical Use
Different sources of media describe the Clinical Use of 2398-96-1 differently. You can refer to the following data:
1. 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.
2. Tolnaftate (Tinactin, others) is a nonprescription antifungal
agent effective in the topical treatment of dermatophyte
infections and tinea. The mechanism of action
is unknown.
Safety Profile
Mtldly toxic by
ingestion. An experimental teratogen. When
heated to decomposition it emits toxic
fumes of SOx and NOx. A fungicide used to
control athlete's foot. See also ESTERS and
CARBAMATES.
Synthesis
Tolnaftate, O-(2-naphthyl)-N-methyl-N-(3-tolyl)-thiocarbamate (35.4.9), is synthesized by reacting equimolar amounts of 2-naphthol and thiophosgene to make a monosubstituted product of thiophosgene (35.4.8), which is then reacted with N-methyl-3-toluidine to
give the desired tolnaftate.
Check Digit Verification of cas no
The CAS Registry Mumber 2398-96-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,9 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2398-96:
(6*2)+(5*3)+(4*9)+(3*8)+(2*9)+(1*6)=111
111 % 10 = 1
So 2398-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3
2398-96-1Relevant articles and documents
NANOEMULSIONS HAVING REVERSIBLE CONTINUOUS AND DISPERSED PHASES
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, (2017/08/01)
A nanoemulsion having reversible continuous and dispersed phases. The nanoemulsion includes an aqueous phase and an oil phase, a weight ratio of the aqueous phase to the oil phase being 1:40-100:1. In the nanoemulsion, the aqueous phase is dispersed as nanosized droplets in the oil phase or the oil phase is dispersed as nanosized droplets in the aqueous phase. The aqueous phase contains water or a water solution and a water-soluble organic nanostructure stabilizer. The oil phase contains an oil or an oil solution, an organic gel thickener, and a hydrophilic surfactant having a hydrophilic-lipophilic balance value greater than 8.0. Also disclosed is a method for preparing the above-described nanoemulsion.
