TOLNAFTATE

PRODUCT IDENTIFICATION

CAS NO. 2398-96-1; 94256-64-1

 

EINECS NO. 219-266-6
FORMULA C19H17NOS
MOL WT. 307.41

H.S. CODE

2930.90.2900

TOXICITY

Rat LD50 (oral): > 6gm/kg
SYNONYMS Tinactin; Tolnaphthate; Chinofungin; Dermoxin;
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate; m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester; Focusan; Methyl(3-methylphenyl)carbamothioic acid O-2-naphthyl ester; N,3'-Dimethylthiocarbanilic acid O-2-naphthyl ester; Naphthiomate t; Naphthyl N-Methyl-N-(3-tolyl)thionocarbamate; O-2-Naphthyl m,N-dimethylthiocarbanilate;

SMILES

c12c(cc(OC(N(c3cc(ccc3)C)C)=S)cc1)cccc2

CLASSIFICATION

Antibiotic, AntiInfective; Antifungal; Carbamate, Thionocarbamate;

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white powder
MELTING POINT 110.5 - 111.5 C
BOILING POINT  
SPECIFIC GRAVITY

 

SOLUBILITY IN WATER 24 g/l
pH  
VAPOR DENSITY

 

REFRACTIVE INDEX

480 C

log Pow 5.81 (Octanol-water)
OH RATE 4.01E-10 (cm3/molecule-sec at 25 C Atmospheric)
AUTOIGNITION

 

NFPA RATINGS Health: 2; Flammability: ; Reactivity: 0
FLASH POINT

240 C

STABILITY

Stable under ordinary conditions

GENERAL DESCRIPTION & EXTERNAL LINKS

Tolnaftate is a carbamate (ester of carbanilic acid) antifungal agent to treat fungus infections on skin and foot such as body ringworm, jock itch and including athlete's foot.

Wikipedia Linking: http://en.wikipedia.org/wiki/Tolnaftate

http://www.mycology.adelaide.edu.au/
The cutaneous mycoses are superficial fungal infections of the skin, hair or nails. Essentially no living tissue is invaded, however a variety of pathological changes occur in the host because of the presence of the infectious agent and/or its metabolic products. The principle aetiological agents are dermatophytic moulds belonging to the genera Microsporum, Trichophyton and Epidermophyton which cause ringworm or tinea of the scalp, glabrous skin and nails; Malassezia fufur, a lipophilic yeast responsible for pityriasis versicolor, follicular pityriasis, seborrhoeic dermatitis and dandruff; and Candida albicans and related species, causing candidiasis of skin, mucous membranes and nails. The usual approach to the management of cutaneous infections is to treat with topical agents if possible, but nail and hair infections, widespread dermatophytosis and chronic non-responsive yeast infections are best treated with oral antifungal agents. Topical agents include Nystatin; the Imidazoles such as Clotrimazole, Miconazole, Econazole, Ketoconazole and Bifonazole; Terbinafine and Tolnaftate. Oral agents include Griseofulvin, Ketoconazole, Fluconazole, Itraconazole, and Terbinafine.........

http://www.cehs.siu.edu/
Many antifungals are available but some are very toxic to the host and must be used with caution. Topical powders and creams often contain tolnaftate or azole derivatives (miconazole, clotrimazole, econazole) and are useful against superficial dermatophytes. Hair or nail disease may be treated with oral griseofulvin, but it is rather toxic. Sporotrichosis may be treated using potassium iodide or amphotericin B (oral). Systemic infections are generally treated by amphotericin B, 5-flourocytosine, miconazole or ketoconazole.

http://lib.bioinfo.pl/
Comparison of in vitro activity of undecylenic acid and tolnaftate against athlete's foot fungi.
[My paper] L P Amsel, L Cravitz, R VanderWyk, S Zahry
Undecylenic acid and tolnaftate were tested in an in vitro test system to evaluate their relative "killing time" efficacy against Trichophyton mentagrophytes, Trichophyton rubrum, and Epidermophyton floccosum. Commercial products containing these active agents were tested similarly. The pure active agents were equivalent in activity. The commercial product containing undecylenic acid appeared to be more effective against the test organisms than did the product containing tolnaftate.

http://www.webmd.com/
The most common antifungals used to treat ringworm of the skin are:

  • Allylamines, such as terbinafine (Lamisil). Allylamines come as creams, pills, and gels. Terbinafine also comes as oral granules, which are little grains that can be sprinkled over food and easily swallowed. Lamisil is available as a cream without a prescription.
  • Azoles. Oral prescription forms include fluconazole (Diflucan) and itraconazole (Sporanox). Some of these medicines are available without a prescription. Brand names include Micatin, Monistat-Derm, and Lotrimin.
  • Griseofulvin (Fulvicin U/F, Grifulvin V, Grisactin). Griseofulvin comes in pill form and requires a prescription.
  • Other antifungals such as tolnaftate (Tinactin). Tinactin is available without a prescription and comes in lotion, cream, gel, and spray forms.

http://www.sigmaaldrich.com/
Tolfanate is an antifungal compound which has activity against such species as Epidermophyton, Microsporum, Trichophyton species, and Malassezia furfur. Its proposed mechanism of action includes the inhibition of squalene epoxidase. The use of tolfanate to inhibit squalene epoxidase activity in Candida albicans (500 M) and in Trichophyton rubrum (IC50 = 51.5 nM) has been studied. The activities of various antifungal compounds, including tolfanate, against dermatophytes from different species have been investigated.6 An in vitro investigation of tolfanate penetration into the human nail plate in the presence of N-acetyl-L-cysteine or 2-mercaptoethanol has been described.7 The effect of tolfanate on the biosynthesis of lipids in Aspergillus niger protoplasts has been studied....

SALES SPECIFICATION

APPEARANCE

white powder

PURITY

98.0 - 102.0 %

MELTING POINT 110 - 113 C

LOSS ON DRYING

0.5% max

TRANSPORTATION
PACKING

25kgs in fiber drum

HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: T, Risk Phrases: 25-36/37/38, Safety Phrases: 26-28A-37/39-45