U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H17NOS
Molecular Weight 307.409
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLNAFTATE

SMILES

CN(C(=S)OC1=CC=C2C=CC=CC2=C1)C3=CC(C)=CC=C3

InChI

InChIKey=FUSNMLFNXJSCDI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H17NOS
Molecular Weight 307.409
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tolnaftate is a thiocarbamate derivative used as an over-the-counter anti-fungal agent for treatment of athlete's foot and ringworm. Tolnaftate acts by inhibition of ergosterol biosynthesis pathway in fungal cells.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TINACTIN
Curative
TINACTIN
Curative
TINACTIN
Curative
TINACTIN
Curative
TINACTIN

PubMed

Sample Use Guides

In Vivo Use Guide
Apply topically to the infected skin as a 1% cream, aerosol liquid spray, aerosol powder spray, powder, or solution.
Route of Administration: Topical
In Vitro Use Guide
Ergosterol biosynthesis in fungal cells from Candida albicans, Candida parapsilosis and Trichophyton mentagrophytes was measured by incubation of cells were incubated with [U-14C]acetate at pH 6.5 for 2 hrs and quantification of nonsaponifiable lipids by thin layer chromatography. Tolnaftate inhibited ergosterol biosynthesis with IC50 of about 0.1-1.0 mg/l.
Substance Class Chemical
Record UNII
06KB629TKV
Record Status Validated (UNII)
Record Version