Tolnaftate
- Product Name
- Tolnaftate
- CAS No.
- 2398-96-1
- Chemical Name
- Tolnaftate
- Synonyms
- TOLNAFTATE USP;Tolnaflate;Aftate;Pitrex;sorgoa;Tritin;Focusan;Timoped;Tinavet;naftate
- 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)
- NIST Chemistry Reference
- Tolnaftate(2398-96-1)
- EPA Substance Registry System
- Tolnaftate (2398-96-1)
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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- PHR1778
- Product name
- Tolnaftate
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 1g
- Price
- $243
- Updated
- 2024/03/01
- Product number
- 1671006
- Product name
- Tolnaftate
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 200mg
- Price
- $393
- Updated
- 2024/03/01
- Product number
- T3059
- Product name
- Tolnaftate
- Purity
- >97.0%(HPLC)(N)
- Packaging
- 1g
- Price
- $47
- Updated
- 2024/03/01
- Product number
- T3059
- Product name
- Tolnaftate
- Purity
- >97.0%(HPLC)(N)
- Packaging
- 5g
- Price
- $139
- Updated
- 2024/03/01
- Product number
- J61834
- Product name
- Tolnaftate
- Packaging
- 1g
- Price
- $63
- Updated
- 2024/03/01
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 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.
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.
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.
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.
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
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.
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.
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.
Tolnaftate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Tolnaftate manufacturers
- Product
- Tolnaftate 2398-96-1
- Price
- US $45.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 tons
- Release date
- 2024-11-28
- Product
- Tolnaftate 2398-96-1
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 0.98
- Supply Ability
- 1000
- Release date
- 2024-05-22
- Product
- Tolnaftate 2398-96-1
- Price
- US $161.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2021-06-04