vaborbactam   Click here for help

GtoPdb Ligand ID: 10871

Synonyms: compound 9f [PMID: 25782055] | RPX-7009 | RPX7009 | Vabomere (vaborbactam + meropenem)
Approved drug PDB Ligand
vaborbactam is an approved drug (FDA (2017), EMA (2018))
Compound class: Synthetic organic
Comment: Vaborbactam is a β-lactamase inhibitor [3]. Structurally it is based on a cyclic boronic acid pharmacophore.

vaborbactam is commercially available from our sponsors

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 6
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 124.1
Molecular weight 297.08
XLogP 0.33
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 O=C(Cc1cccs1)N[C@H]1CC[C@H](OB1O)CC(=O)O
Isomeric SMILES O=C(Cc1cccs1)N[C@H]1CC[C@H](OB1O)CC(=O)O
InChI InChI=1S/C12H16BNO5S/c15-11(7-9-2-1-5-20-9)14-10-4-3-8(6-12(16)17)19-13(10)18/h1-2,5,8,10,18H,3-4,6-7H2,(H,14,15)(H,16,17)/t8-,10-/m0/s1
InChI Key IOOWNWLVCOUUEX-WPRPVWTQSA-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
A combination of vaborbactam plus meropenem (Vabomere) is approved by the FDA as a treatment for serious urinary tract infections [2,4]. The same combination is authorised in the EU with the trade name Vaborem.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02168946 Efficacy, Safety, Tolerability of Vabomere Compared to Best Available Therapy in Treating Serious Infections in Adults Phase 3 Interventional Melinta Therapeutics, Inc. 1,6
NCT02166476 Efficacy/Safety of Meropenem-Vaborbactam Compared to Piperacillin-Tazobactam in Adults With cUTI and AP Phase 3 Interventional Melinta Therapeutics, Inc. 5
External links Click here for help
For extended ADME data see the following:

Drugs.com