epetraborole   Click here for help

GtoPdb Ligand ID: 13079

Synonyms: AN3365 | BRII-658 | GSK2251052
Compound class: Synthetic organic
Comment: Epetraborole (GSK2251052) is an aminomethylbenzoxaborole antibacterial compound that is an inhibitor of bacterial leucyl-tRNA synthetase (LeuRS) [2]. It is being developed for the treatment of non-tuberculous mycobacterial pulmonary disease (NTM-PD).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 84.94
Molecular weight 237.06
XLogP -0.83
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C1=CC(=C2C(=C1)[C@@H](CN)OB2O)OCCCO
Isomeric SMILES B1(C2=C(C=CC=C2OCCCO)[C@H](O1)CN)O
InChI InChI=1S/C11H16BNO4/c13-7-10-8-3-1-4-9(16-6-2-5-14)11(8)12(15)17-10/h1,3-4,10,14-15H,2,5-7,13H2/t10-/m1/s1
InChI Key FXQIIDINBDJDKL-SNVBAGLBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Epetraborole was first developed by GlaxoSmithKline as a treatment for Gram-negative infections. It advanced to Phase 2 evaluation for complicated urinary tract infections (cUTIs; NCT01381549) and complicated intra-abdominal infections (cIAIs; NCT01381562) but these were terminated due to resistance developing in patients during the cUTI trial [3].
Epetraborole is currently being clinically developed by AN2 Therapeutics as a once-daily oral treatment for patients with chronic NTM-PD caused by Mycobacterium avium Complex (MAC) (NCT05327803).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05327803 Study of Epetraborole in Patients With Treatment-refractory MAC Lung Disease Phase 2/Phase 3 Interventional AN2 Therapeutics, Inc
NCT01381549 GSK2251052 in Complicated Urinary Tract Infection Phase 2 Interventional GlaxoSmithKline The study was halted early in enrolment due to the emergence of epetraborole resistance in bacterial isolates from a subgroup of participants. 3
NCT01381562 GSK2251052 in the Treatment of Complicated Intra-abdominal Infections Phase 2 Interventional GlaxoSmithKline The study was terminated due to the microbiological findings in the associated cUTI trial. 3