tavaborole

CHEBI:77942 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A member of the class of benzoxaboroles that is 1,3-dihydro-1-hydroxy-2,1-benzoxaborole substituted at position 5 by a fluoro group. A topical antifungal agent used for the treatment of onychomycosis (fungal infection of the toenails and fingernails). — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:37143
• Label unavailable CHEBI:78240

Chemical structure

SMILES

OB1OCc2cc(F)ccc21

InChI

InChI=1S/C7H6BFO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2

Also called

• 5-fluoro-2,1-benzoxaborol-1(3H)-ol (EXACT_SYNONYM)— chebi
• 5-Fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (EXACT_SYNONYM)— chebi
• AN 2690 (EXACT_SYNONYM)— chebi
• AN-2690 (EXACT_SYNONYM)— chebi
• AN2690 (EXACT_SYNONYM)— chebi

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.

• cas:174671-46-6
• reaxys:10657796

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.

• drugcentral:4877
• kegg.drug:D10169

Activity roles

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

• antifungal agent CHEBI:35718

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.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

cytoplasmic leucyl-tRNA synthetase-tRNA(Leu) editing complex PROTEIN_COMPLEX DIRECT_BINDING_TARGET

Biochemical and structural experiments showed a boron-mediated tRNA(Leu)-AN2690 adduct trapped in the yeast LeuRS editing site, preventing catalytic turnover. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2007-06 (retrieved 2026-09-02).

• PMID:17588934 (Primary tavaborole tRNA-trapping mechanism study (DOI:10.1126/science.1142189).)

Mechanism summary

Mode of action

PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:17588934 showed that tavaborole (AN2690) forms a stable covalent adduct with the terminal adenosine of tRNA(Leu) in the editing site of yeast cytoplasmic leucyl-tRNA synthetase. Trapping enzyme-bound tRNA prevents leucyl-tRNA synthesis and thereby blocks protein synthesis.

Clinical status

APPROVED

Record-level evidence

• PMID:17588934 (Primary exact-tavaborole LeuRS editing-site and protein-synthesis study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (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 2026-08-31 · 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. REVIEWED 2026-09-02 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, antifungal role, filing class, and retained FDA assertions; curator-confirmed protein-synthesis inhibition and added the directly observed LeuRS-tRNA editing complex.

7. RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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