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Tolnaftate

CAS No.2398-96-1
Chemical Name:Tolnaftate
CBNumber:CB4396231
Molecular Formula:C19H17NOS
Formula Weight:307.41
MOL File:2398-96-1.mol

Tolnaftate Property

Melting point 110.5-111.5°C
Boiling point 453.4±38.0 °C(Predicted)
Density 1.1328 (rough estimate)
refractive index 1.6970 (estimate)
storage temp. Sealed in dry,2-8°C
solubility Soluble in chloroform at 50 mg/ml. Sparingly soluble in ethanol or methanol
form powder
pka -0.35±0.50(Predicted)
color white to off-white
Water Solubility <0.1 g/100 mL at 22 ºC
λmax 258nm(MeOH)(lit.)
Merck 14,9519
InChIKey FUSNMLFNXJSCDI-UHFFFAOYSA-N
LogP 5.142 (est)
EWG's Food Scores 1-4
FDA UNII 06KB629TKV
ATC code D01AE18
NIST Chemistry Reference Tolnaftate(2398-96-1)
EPA Substance Registry System Tolnaftate (2398-96-1)
UNSPSC Code 51302004
NACRES NA.85

Safety

WGK Germany :2
RTECS :FD8891300
TSCA :Yes
HazardClass :IRRITANT
HS Code :2930206050
Toxicity :LD50 in mice, rats (g/kg): >10, >6 orally; >6, >4 s.c. (Hashimoto)

NFPA 704:

	0
3		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H335
Precautionary statements P261-P305+P351+P338

Tolnaftate Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: T6638
Product name : Tolnaftate
Purity:
Packaging: 1G
Price: ₹6419.23
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: T6638
Product name : Tolnaftate
Purity:
Packaging: 5G
Price: ₹17255.05
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1778
Product name : Tolnaftate
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹21812.38
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: T3059
Product name : Tolnaftate
Purity:
Packaging: 1G
Price: ₹3900
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: T3059
Product name : Tolnaftate
Purity:
Packaging: 5G
Price: ₹9000
Updated: 2022/05/26
Buy: Buy

Tolnaftate Chemical Properties,Usage,Production

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 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.
Uses 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.
Uses 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.
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.
Air & Water Reactions Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Insoluble in water.
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 Tolnaftate (Tinactin, others) is a nonprescription antifungal agent effective in the topical treatment of dermatophyte infections and tinea. The mechanism of action is unknown.
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.
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.