AntibioticMech

butenafine

CHEBI:3238 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

Trimethylamine in which hydrogen atoms attached to different methyl groups are substituted by 1-naphthyl and 4-tert-butylphenyl groups. It is an inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes, and is used as its hydrochloride salt for treatment of dermatological fungal infections. — ChEBI

Classification

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:25477 CHEBI:25477
• CHEBI:32876 CHEBI:32876
• ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties

Molecular formula	C23H27N
Charge	0
Average mass	317.476 Da
Monoisotopic mass	317.21435 Da
Source	ChEBI
InChIKey	ABJKWBDEJIDSJZ-UHFFFAOYSA-N

SMILES

CN(Cc1ccc(C(C)(C)C)cc1)Cc1cccc2ccccc12

InChI

InChI=1S/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3

Also called

• butenafinum (INN)— chebi
• 1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine (EXACT_SYNONYM)— chebi
• (4-tert-Butyl-benzyl)-methyl-naphthalen-1-ylmethyl-amine (EXACT_SYNONYM)— chebi
• (4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine (EXACT_SYNONYM)— chebi
• 4-tert-butylbenzyl(methyl)(1-naphthalenemethyl)amine (EXACT_SYNONYM)— chebi
• Butenafine (EXACT_SYNONYM)— chebi
• N-(p-tert-butylbenzyl)-N-methyl-1-naphthalenemethylamine (EXACT_SYNONYM)— chebi
• butenafina (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3009173
• beilstein:6334654
• cas:101828-21-1
• drugbank:DB01091
• drugcentral:444
• kegg.compound:C08067
• kegg.drug:D07596
• lincs.smallmolecule:LSM-5956
• patent:EP164697
• patent:US5021458
• wikipedia.en:Butenafine
• chembl:CHEMBL990
• pubchem.compound:2484

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:3009173	butenafine	antibioticmech:aro-e73f50f1ef	2026-08-30
CHEBI	CHEBI:3238	butenafine	antibioticmech:chebi-a19fbfa560	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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. 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.