A thiocarbamate antifungal agent
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Labeled Version(s)
29048Tolnaftate-d7
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Tolnaftate

Item No. 21446

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-methyl-N-(3-methylphenyl)-carbamothioic acid, O-2-naphthalenyl ester
CAS Number
2398-96-1
Synonyms
  • NSC 233648
  • SCH 10144
Molecular Formula
C19H17NOS
Formula Weight
307.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 15 mg/mlEthanol: Slightly soluble
λmax
223, 258 nm
SMILES
CN(C1=CC(C)=CC=C1)C(OC2=CC3=CC=CC=C3C=C2)=S
InChi Code
InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3
InChi Key
FUSNMLFNXJSCDI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Tolnaftate is a thiocarbamate antifungal agent.1 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).2,3 Tolnaftate also reduces aflatoxin production in A. parasiticus in a concentration-dependent manner.4 It inhibits squalene epoxidase with an IC50 value of 12.5 µg/ml in a cell-free assay.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ryder, N.S., Frank, I., and Dupont, M.C. Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob. Agents Chemother. 29(5), 858-860 (1986).

    2. Petranyi, G., Meingassner, J.G., and Mieth, H. Antifungal activity of the allylamine derivative terbinafine in vitro. Antimicrob. Agents Chemother. 31(9), 1365-1368 (1987).

    3. Waitz, J.A., Moss, E.L., and Weinstein, M.J. Chemotherapeutic evaluation of clotrimazole [Bay b 5097, 1 (o-chloro-α-α-diphenylbenzyl) imidazole]. Appl. Microbiol. 22(5), 891-898 (1971).

    4. Khan, S.N., Maggon, K.K., and Venkitasubramanian, T.A. Inhibition of aflatoxin biosynthesis by tolnaftate. Appl. Environ. Microbiol. 36(2), 270-273 (1978).