terbinafine

CHEBI:9448 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A tertiary amine that is N-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(tertbutylethynyl)allyl group. An antifungal agent administered orally (generally as the hydrochloride salt) for the treatment of skin and nail 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:59831 CHEBI:59831
CHEBI:73474 CHEBI:73474
CHEBI:87127 CHEBI:87127
ARO:3007498 ARO:3007498

Chemical structure

Computed structure properties
Molecular formula	C21H25N
Charge	0
Average mass	291.438 Da
Monoisotopic mass	291.1987 Da
Source	ChEBI
InChIKey	DOMXUEMWDBAQBQ-WEVVVXLNSA-N

SMILES

CN(C/C=C/C#CC(C)(C)C)Cc1cccc2ccccc12

InChI

InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+

Also called

terbinafina (INN)— chebi
terbinafinum (INN)— chebi
(2E)-N,6,6-trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine (EXACT_SYNONYM)— chebi
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine (EXACT_SYNONYM)— chebi
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3007507
cas:91161-71-6
drugbank:DB00857
drugcentral:2597
hmdb:HMDB0014995
kegg.compound:C08079
kegg.drug:D02375
metacyc.compound:CPD-10571
reaxys:4256376
wikipedia.en:Terbinafine
chembl:CHEMBL822
pubchem.compound:1549008

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:3007507`	terbinafine	`antibioticmech:aro-7b45a31503`	2026-08-30
CHEBI	`CHEBI:9448`	terbinafine	`antibioticmech:chebi-b78967d26d`	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.
Clinical status: APPROVED

Resistance mechanisms

11 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

UNKNOWN 6

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Arthroderma vanbreuseghemii squalene epoxidase enzyme with mutations associated with resistance to terbinafine	ARO:3009269	not organism-specific	—	ARO:3009269 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
Candida albicans TAC1 with mutations conferring resistance to terbinafine	ARO:3009427	not organism-specific	—	ARO:3009427 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
ErgA(F389L) (amino acid mutation) [Ectopic] associated with resistance to terbinafine This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ATCC 13073 `NCBITaxon:330879` `UniProtKB:E9R5G2` Afu5g07780-T `PHIPO:0000387`	—	PMID:16801438 (PHI-base primary-literature antimicrobial interaction PHIG:6409; joined to this record by exact ChEBI identifier.) Cell growth assay
Trychophyton rubrum squalene epoxidase enzyme with mutations associated with resistance to terbinafine	ARO:3009270	not organism-specific	—	ARO:3009270 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
cox10 transformant(W004-cox10(R243Q)) (transformant) [Not assayed] associated with resistance to terbinafine This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Aspergillus fumigatus `NCBITaxon:746128` strain A1160C `NCBITaxon:451804` `UniProtKB:B0Y628` `PHIPO:0000387`	—	PMID:27799210 (PHI-base primary-literature antimicrobial interaction PHIG:8689; joined to this record by exact ChEBI identifier.) Cell growth assay
erg1+ (wild type) [Overexpression] associated with resistance to terbinafine This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Aspergillus fumigatus `NCBITaxon:746128` strain AF293.1 `NCBITaxon:330879` `UniProtKB:E9R5G2` Afu5g07780-T `PHIPO:0000387`	—	PMID:15215099 (PHI-base primary-literature antimicrobial interaction PHIG:6409; joined to this record by exact ChEBI identifier.) Cell growth assay

ANTIBIOTIC_EFFLUX 5

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Candida albicans CDR2 with mutations conferring resistance to azoles	ARO:3007554	not organism-specific	—	ARO:3007554 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
Microsporum canis MDR1 with mutations conferring resistance to terbinafine	ARO:3009449	not organism-specific	—	ARO:3009449 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
Microsporum canis MDR2 with mutations conferring resistance to terbinafine	ARO:3009450	not organism-specific	—	ARO:3009450 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
Microsporum canis MDR4 with mutations conferring resistance to terbinafine	ARO:3009454	not organism-specific	—	ARO:3009454 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)
fungal MDR	ARO:3009425	not organism-specific	—	ARO:3009425 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007507 (terbinafine); database assertion, not a primary citation.)

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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · 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.