ledaborbactam   Click here for help

GtoPdb Ligand ID: 13082

Synonyms: VNRX-5236
Compound class: Synthetic organic
Comment: Ledaborbactam (VNRX-5236) is a novel broad-spectrum boronic acid β-lactamase inhibitor (BLI). It is a reversible covalent inhibitor of serine β-lactamases (classes A, C, D) [1].
Ledaborbactam etzadroxil (VNRX-7145, PubChem CID 138455030), an orally bioavailable prodrug of ledaborbactam [3], is being developed in combination with ceftibuten for the treatment of infections caused by drug-resistant Enterobacterales.
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 CDK toolkit. 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 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 95.86
Molecular weight 263.05
XLogP 0.49
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCC(=O)N[C@H]1CC2=CC=CC(=C2OB1O)C(=O)O
Isomeric SMILES B1([C@H](CC2=C(O1)C(=CC=C2)C(=O)O)NC(=O)CC)O
InChI InChI=1S/C12H14BNO5/c1-2-10(15)14-9-6-7-4-3-5-8(12(16)17)11(7)19-13(9)18/h3-5,9,18H,2,6H2,1H3,(H,14,15)(H,16,17)/t9-/m0/s1
InChI Key QAGGLFCWUVSERJ-VIFPVBQESA-N
References
1. Chatwin CL, Hamrick JC, Trout REL, Myers CL, Cusick SM, Weiss WJ, Pulse ME, Xerri L, Burns CJ, Moeck G et al.. (2021)
Microbiological Characterization of VNRX-5236, a Broad-Spectrum β-Lactamase Inhibitor for Rescue of the Orally Bioavailable Cephalosporin Ceftibuten as a Carbapenem-Sparing Agent against Strains of Enterobacterales Expressing Extended-Spectrum β-Lactamases and Serine Carbapenemases.
Antimicrob Agents Chemother, 65 (8): e0055221. [PMID:34001510]
2. Karlowsky JA, Wise MG, Hackel MA, Pevear DC, Moeck G, Sahm DF. (2022)
Ceftibuten-Ledaborbactam Activity against Multidrug-Resistant and Extended-Spectrum-β-Lactamase-Positive Clinical Isolates of Enterobacterales from a 2018-2020 Global Surveillance Collection.
Antimicrob Agents Chemother, 66 (11): e0093422. [PMID:36286518]
3. Trout RE, Zulli A, Mesaros E, Jackson RW, Boyd S, Liu B, Hamrick J, Daigle D, Chatwin CL, John K et al.. (2021)
Discovery of VNRX-7145 (VNRX-5236 Etzadroxil): An Orally Bioavailable β-Lactamase Inhibitor for Enterobacterales Expressing Ambler Class A, C, and D Enzymes.
J Med Chem, 64 (14): 10155-10166. [PMID:34191513]