naftifine

CHEBI:7451 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A tertiary amine in which the nitrogen is substituted by methyl, α-naphthylmethyl, and (1E)-cinnamyl groups. It is used (usually as its hydrochloride salt) for the treatment of fungal skin infections. — 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

allylamine antifungalARO:3007498

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25477 CHEBI:25477
CHEBI:32876 CHEBI:32876
CHEBI:87127 CHEBI:87127
ARO:3007498 ARO:3007498

Chemical structure

Computed structure properties
Molecular formula	C21H21N
Charge	0
Average mass	287.406 Da
Monoisotopic mass	287.1674 Da
Source	ChEBI
InChIKey	OZGNYLLQHRPOBR-DHZHZOJOSA-N

SMILES

CN(C/C=C/c1ccccc1)Cc1cccc2ccccc12

InChI

InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+

Also called

naftifina (INN)— chebi
naftifinum (INN)— chebi
(2E)-N-methyl-N-(1-naphthylmethyl)-3-phenylprop-2-en-1-amine (EXACT_SYNONYM)— chebi
(E)-N-cinnamyl-N-methyl-1-naphthalenemethylamine (EXACT_SYNONYM)— chebi
naftifin (EXACT_SYNONYM)— chebi
trans-N-cinnamyl-N-methyl-(1-naphthylmethyl)amine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3007506
cas:65472-88-0
drugbank:DB00735
drugcentral:1872
hmdb:HMDB0014873
kegg.compound:C08071
kegg.drug:D08245
patent:BE853976
patent:US4282251
reaxys:2983617
wikipedia.en:Naftifine
chembl:CHEMBL626
pubchem.compound:47641

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:3007506`	naftifine	`antibioticmech:aro-a83456ba03`	2026-08-30
CHEBI	`CHEBI:7451`	naftifine	`antibioticmech:chebi-86e1c7d6c5`	2026-08-30

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:59285 (EC 1.14.13.132 (squalene monooxygenase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

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
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.