tolnaftate

Also known as Aftate, SCH-10144, Tinactin, O-2-Naphthyl m,N-dimethylthiocarbanilate, Tolnaphthate, m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester, N-Methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide, 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate

Tolnaftate (INN), sold under the brand names TAGRID, and Tinactin, among others, is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm. Tolnaftate was discovered by Teruhisa Noguchi in 1962 while he was working for the Nippon Soda Company.

Chemical data

Formula: C19H17NOS
Molecular weight: 307.4 g/mol
IUPAC name: O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate
SMILES: CC1=CC(=CC=C1)N(C)C(=S)OC2=CC3=CC=CC=C3C=C2
InChIKey: FUSNMLFNXJSCDI-UHFFFAOYSA-N
XLogP: 5.5
Polar surface area: 44.6 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

314 papers

Tolnaftate.2006
Tinea pedis: an updated review.Drugs in context · 2023
Otomycosis: Diagnosis and treatment.Clinics in dermatology · 2010
Tolnaftate inhibits ergosterol production and impacts cell viability of Leishmania sp.Bioorganic chemistry · 2020
Tolnaftate.British medical journal · 1967

via PubMed

Wikidata facts

Mass: 307.103085

Show 4 more facts

chemical formula: C₁₉H₁₇NOS
canonical SMILES: CC1=CC(=CC=C1)N(C)C(=S)OC2=CC3=CC=CC=C3C=C2
World Health Organisation international non-proprietary name: tolnaftate
Commons category: Tolnaftate

Sources (2)

via Wikidata · CC0

~2 min read

Article

6 sections

Contents

Mechanism
Uses
Side effects
See also
References
External links

==Mechanism== Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase, an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.