T6638

Sigma-Aldrich

Tolnaftate

Synonym(s):
Methyl-(3-methylphenyl)carbamothioic acid O-2-naphthyl ester
Empirical Formula (Hill Notation):
C19H17NOS
CAS Number:
Molecular Weight:
307.41
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

form

powder

Quality Level

storage condition

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

color

white to off-white

solubility

chloroform: soluble 50 mg/mL

Mode of action

enzyme | inhibits

antibiotic activity spectrum

fungi

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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Related Categories

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.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T6638.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Toma Kezutyte et al.
Acta poloniae pharmaceutica, 67(4), 327-334 (2010-07-20)
Abstract: Tolnaftate, an antifungal of thiocarbamate class, is used topically in 1% formulations. Its penetration into skin layers is a prerequisite for tolnaftate action against dermatophytes. The aim of this work was to optimize and validate a simple, rapid, accurate...
A K Dash et al.
Journal of pharmaceutical sciences, 91(4), 983-990 (2002-04-12)
Ethylcellulose microspheres containing tolnaftate (I) were prepared by the emulsion-solvent evaporation technique. An X-ray powder diffractometric method was developed to quantify the content of crystalline I in these microspheres. X-ray lines of I with d-spacings of 5.5 and 4.2 A...
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...
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...

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