AntibioticMech

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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.

Chemical structure

Computed structure properties
Molecular formulaC21H25N
Charge0
Average mass291.438 Da
Monoisotopic mass291.1987 Da
SourceChEBI
InChIKeyDOMXUEMWDBAQBQ-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

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

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
SourceNative IDLabelMinted CURIEVersion
ARO ARO:3007507 terbinafine antibioticmech:aro-7b45a31503 2026-08-30
CHEBI CHEBI:9448 terbinafine antibioticmech:chebi-b78967d26d 2026-08-30

Related pathway records

Evidence-qualified relationships to a pinned corpus revision.

PathwayMech: gomodel:YeastPathways_PWY-5670-1RELATED_PATHWAY_ACTIVITY
PMID:10991846 identifies the squalene-epoxidase step targeted by terbinafine in the Candida sterol pathway. The linked epoxysqualene pathway represents the corresponding S. cerevisiae activity; no same-strain or drug-sensitivity assertion.
Source revision: aa305727458c44ab05614901334540e2c87a9f3a

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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 6
UNKNOWN
DeterminantARO IDOrganismGene familiesEvidence
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. Grounding review terbinafine-2006-reference-context: The source ATCC 13073 label denotes the parent background, not either separately named tested derivative. UniProtKB:E9R5G2, the retained gene_id and TaxID 330879 identify the Af293 reference locus and strain. Multiple subjects must not be collapsed to an exact allele or strain identifier. Source alterations, phenotypes and assays are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:E9R5G2.		 — Aspergillus fumigatus NCBITaxon:746128
strain ATCC 13073 Afu5g07780-T
PHIPO:0000387		 —
  • PMID:16801438 (PHI-base primary-literature antimicrobial interaction PHIG:6409; joined to this record by exact ChEBI identifier.)
  • DOI:10.1128/aac.00187-06 (Identifier-scope review: Results and Figure 2: parent distinguished from multiple tested derivatives, Table 1: strain identities only, UniProtKB release 2026_03: E9R5G2 entry 72, sequence version 1; reference locus and taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
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. Grounding review wei-2016-reference-context-followup: The source strain label denotes a parent background, not an individual tested derivative. Af293 and A1163/CEA10 UniProt entries and strain TaxIDs describe reference context. The retained gene_id is a reference-locus identifier, not an experimental allele. Increased frequency of later colonies is distinct from baseline susceptibility, and plate growth is not a broth MIC or a clinical resistance category. These endpoint distinctions remain review limitations, not new activity observations. Source alterations, phenotypes and assays are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:451804; protein_accession=UniProtKB:B0Y628.		 — Aspergillus fumigatus NCBITaxon:746128
strain A1160C
PHIPO:0000387		 —
  • PMID:27799210 (PHI-base primary-literature antimicrobial interaction PHIG:8689; joined to this record by exact ChEBI identifier.)
  • DOI:10.1128/aac.02101-16 (Identifier-scope review: Results and Figures 1-4: baseline parent versus separate tested groups, Tables 1-2: subject identity and distinct assay endpoints, UniProtKB release 2026_03: Q4WNT5 entry 146; B0XYD8 entry 86; B0Y628 entry 66; all sequence version 1; reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
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. Grounding review terbinafine-2004-reference-context: The source AF293.1 label denotes a parent background, not one uniquely identified tested derivative. UniProtKB:E9R5G2, the retained gene_id and TaxID 330879 describe Af293 reference context. Parent lineage does not establish an exact experimental protein or subject TaxID, and disk-diffusion and MIC endpoints remain distinct. Source alterations, phenotypes and assays are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:E9R5G2.		 — Aspergillus fumigatus NCBITaxon:746128
strain AF293.1 Afu5g07780-T
PHIPO:0000387		 —
  • PMID:15215099 (PHI-base primary-literature antimicrobial interaction PHIG:6409; joined to this record by exact ChEBI identifier.)
  • DOI:10.1128/aac.48.7.2490-2496.2004 (Identifier-scope review: Results: parent, tested derivatives and control groups are distinct, Tables 1-2: strain labels and endpoint context only, UniProtKB release 2026_03: E9R5G2 entry 72, sequence version 1; reference locus and taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
ANTIBIOTIC_EFFLUX 5
ANTIBIOTIC_EFFLUX
DeterminantARO IDOrganismGene familiesEvidence
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

  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

  5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  7. RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  9. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  10. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  11. ADD_PATHWAY_LINKS 2026-10-05 · codex · LLM-assisted

    Added reviewed PathwayMech relationships and any supported protein example from curation/pathway_links.yaml; organism and evidence limits are recorded in each basis.

  12. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Scoped imported reference protein and strain TaxID to provenance, not tested-subject identity. Source parent labels, alterations, phenotypes and assays preserved; no experimental allele, genome or activity measurement inferred.

  13. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after nine identifier-scope corrections; previous decisions, biological fields and activities unchanged.

  14. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.

  15. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.

  16. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.

  17. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.

  18. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.

  19. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.

  20. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.

  21. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.

  22. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.

  23. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.

  24. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.

  25. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.

  26. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.

  27. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.

  28. RECONCILED_BRANCH_CURATION 2026-10-11 · codex · LLM-assisted

    Integrated main's reviewed PathwayMech links with the resistance-grounding checkpoint; retained both committed event histories and all resistance and activity evidence.

  29. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-12 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.

  30. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-13 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.

Provenance

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

Explore across X-Mech: MediaIngredientMech (terbinafine) · CultureMech · NaturalProductMech · PathwayMech · TraitMech