tolnaftate

CHEBI:9620 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:38128 CHEBI:38128
ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties
Molecular formula	C19H17NOS
Charge	0
Average mass	307.418 Da
Monoisotopic mass	307.10309 Da
Source	ChEBI
InChIKey	FUSNMLFNXJSCDI-UHFFFAOYSA-N

SMILES

Cc1cccc(N(C)C(=S)Oc2ccc3ccccc3c2)c1

InChI

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

Also called

Separin (BRAND_NAME)— chebi
Tinactin (BRAND_NAME)— chebi
tolnaftato (INN)— chebi
tolnaftatum (INN)— chebi
O-2-naphthyl methyl(3-methylphenyl)carbamothioate (EXACT_SYNONYM)— chebi
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate (EXACT_SYNONYM)— chebi
Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl ester (EXACT_SYNONYM)— chebi
N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide (EXACT_SYNONYM)— chebi
O-2-Naphthyl m,N-dimethylthiocarbanilate (EXACT_SYNONYM)— chebi
Tolnaphthate (EXACT_SYNONYM)— chebi
m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009174
cas:2398-96-1
drugbank:DB00525
drugcentral:3617
hmdb:HMDB0005005
kegg.drug:D00381
lincs.smallmolecule:LSM-5554
patent:US2010035939
patent:WO2010037089
reaxys:2752620
wikipedia.en:Tolnaftate
chembl:CHEMBL83668
pubchem.compound:5510

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:86327 CHEBI:86327

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3009174`	tolnaftate	`antibioticmech:aro-49498c70e7`	2026-08-30
CHEBI	`CHEBI:9620`	tolnaftate	`antibioticmech:chebi-f071b8f586`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.