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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
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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)
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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)
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1778
Product name
Tolnaftate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1g
Price
$243
Updated
2024/03/01
Sigma-Aldrich
Product number
1671006
Product name
Tolnaftate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$393
Updated
2024/03/01
TCI Chemical
Product number
T3059
Product name
Tolnaftate
Purity
>97.0%(HPLC)(N)
Packaging
1g
Price
$47
Updated
2024/03/01
TCI Chemical
Product number
T3059
Product name
Tolnaftate
Purity
>97.0%(HPLC)(N)
Packaging
5g
Price
$139
Updated
2024/03/01
Alfa Aesar
Product number
J61834
Product name
Tolnaftate
Packaging
1g
Price
$63
Updated
2024/03/01
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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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Tolnaftate Suppliers

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View Lastest Price from Tolnaftate manufacturers

Apeloa production Co.,Limited
Product
Tolnaftate 2398-96-1
Price
US $1.00/g
Min. Order
1g
Purity
0.98
Supply Ability
1000
Release date
2024-05-22
Baoji Guokang Bio-Technology Co., Ltd.
Product
Tolnaftate 2398-96-1
Price
US $161.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000kg
Release date
2021-06-04
Hebei Weibang Biotechnology Co., Ltd
Product
Tolnaftate 2398-96-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-06

2398-96-1, TolnaftateRelated Search:

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  • 2-naphthyl n-methyl-n-(3-tolyl)thionocarbamate
  • METHYL 3-TOLYLTHIOCARBAMIC ACID O-NAPHTHALEN-2-YL ESTER
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  • m,n-dimethylthio-carbanilicacio-2-naphthylester
  • Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl ester
  • methyl(3-methylphenyl)carbamothioicacido-2-naphthalenylester
  • methyl(3-methylphenyl)-carbamothioicacio-2-naphthalenylester
  • Naphthiomate T
  • naphthiomatet
  • o-(2-Naphthyl) methyl(3-methylphenyl)thiocarbamate
  • Tolnaftate (200 mg)
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  • N-Methyl-N-(3-Methylphenyl)carbaMothioic Acid O-2-Naphthalenyl Ester
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