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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:
2398-96-1
Molecular Weight:
307.41
EC Number:
219-266-6
MDL number:
MFCD00056611
UNSPSC Code:
51302004
PubChem Substance ID:
24900394
NACRES:
NA.85

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. It also has been used as a comparator compound for antifungal efficiency studies.

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. Tolnaftate inhibits biosynthesis of aflatoxin.

Packaging

1G,5G

Other Notes

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

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
089M4807V
116M4783V
086M4750V
056M4792V
BCBK6699V

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Y Kobayashi et al.
Chemical & pharmaceutical bulletin, 46(11), 1797-1802 (1998-12-10)
The enhancing effects of various vehicles on the in vitro permeation of a hydrophilic model drug, 5-fluorouracil (5-FU), or a lipophilic model drug, tolnaftate (TN), through human nail plates were investigated using a modified side-by-side diffusion cell. Tip pieces from
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)
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
Toma Kezutyte et al.
Acta poloniae pharmaceutica, 68(6), 965-973 (2011-12-01)
Five fatty acids (oleic, linoleic, myristic, lauric and capric) were incorporated in 10% (w/w) into ointment formulation and their influence on lipophilic model drug tolnaftate release in vitro and enhancing effect on tolnaftate penetration into epidermis and dermis of human
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