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T6638

Sigma-Aldrich

Tolnaftate

Synonym(s):

Methyl-(3-methylphenyl)carbamothioic acid O-2-naphthyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H17NOS
CAS Number:
Molecular Weight:
307.41
EC Number:
MDL number:
UNSPSC Code:
51302004
PubChem Substance ID:
NACRES:
NA.85
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form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white to off-white

solubility

chloroform: soluble 50 mg/mL

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CN(C(=S)Oc1ccc2ccccc2c1)c3cccc(C)c3

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

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Application

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 ringworm[1]. It also has been used as a comparator compound for antifungal efficiency studies[2].

Biochem/physiol Actions

Tolnaftate prevents ergosterol biosynthesis by inhibiting squalene epoxidase. It has also been reported to distort the hyphae and to stunt mycelial growth in susceptible organisms[1]. Tolnaftate inhibits biosynthesis of aflatoxin.

Packaging

1G,5G

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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T Ohmi et al.
Arzneimittel-Forschung, 41(8), 847-851 (1991-08-01)
In vitro and in vivo antifungal activities of the new imidazole derivative latoconazole ((+-)-(E)-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-1- imidazolylacetonitrile, NND-318; CAS 101530-10-3) were studied in comparison with three major topical agents, clotrimazole, bifonazole and tolnaftate. The in vitro activity of latoconazole against dermatophytes was
L W Tom
The Laryngoscope, 110(4), 509-516 (2000-04-14)
To determine the ototoxic effects of five commonly used topical antimycotic agents-clotrimazole, miconazole, nystatin, tolnaftate, and gentian violet-in the guinea pig. A controlled animal study in which the ototoxicity of commonly used topical antifungal agents was investigated by measurement of
Allergic contact dermatitis from tolnaftate.
R González Pérez et al.
Contact dermatitis, 32(3), 173-173 (1995-03-01)
M P Gupta et al.
Journal of medical and veterinary mycology : bi-monthly publication of the International Society for Human and Animal Mycology, 29(1), 45-52 (1991-01-01)
Studies were performed on the mode of action of tolnaftate and resistance to this drug in Microsporum gypseum. Cells grown in the presence of tolnaftate (at the IC 50) showed a reduced content of total phospholipids and sterols whereas there
S T Patil et al.
Fresenius' journal of analytical chemistry, 367(1), 91-93 (2001-03-03)
Tolnaftate, an antifungal drug (TF) and related impurities arising from synthesis, viz., N-methyl-m-toluidine (NMmT) and beta-naphthol-1-chlorothio carbamate (beta-NCTC) can be determined by supercritical fluid chromatography. Even though it was possible to elute TF completely with neat SCF CO2, the peaks

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