Tolnaftate

Bezeichnung:Tolnaftate

CAS-Nr2398-96-1

Englisch Name:Tolnaftate

CBNumberCB4396231

SummenformelC19H17NOS

Molgewicht307.41

MOL-Datei2398-96-1.mol

Tolnaftate physikalisch-chemischer Eigenschaften

Schmelzpunkt	110.5-111.5°C
Siedepunkt	453.4±38.0 °C(Predicted)
Dichte	1.1328 (rough estimate)
Brechungsindex	1.6970 (estimate)
storage temp.	Sealed in dry,2-8°C
Löslichkeit	Soluble in chloroform at 50 mg/ml. Sparingly soluble in ethanol or methanol
Aggregatzustand	powder
pka	-0.35±0.50(Predicted)
Farbe	white to off-white
Wasserlöslichkeit	<0.1 g/100 mL at 22 ºC
maximale Wellenlänge (λmax)	258nm(MeOH)(lit.)
Merck	14,9519
InChIKey	FUSNMLFNXJSCDI-UHFFFAOYSA-N
LogP	5.142 (est)
NIST chemische Informationen	Tolnaftate(2398-96-1)
EPA chemische Informationen	Tolnaftate (2398-96-1)

Sicherheit

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

Gefahreninformationscode (GHS)

Tolnaftate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
White Solid
Originator
Tinactin,Schering,US,1965
Verwenden
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.
Verwenden
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.
Verwenden
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
Allgemeine Beschreibung
Crystals or white powder.
Air & Water Reaktionen
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.
Reaktivität anzeigen
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.
Brandgefahr
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.
Sicherheitsprofil
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.
Synthese
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.

Tolnaftate Upstream-Materialien And Downstream Produkte

Tolnaftate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

2398-96-1, Tolnaftate Verwandte Suche:

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