funobactam   Click here for help

GtoPdb Ligand ID: 13114

Synonyms: XNW4107
Compound class: Synthetic organic
Comment: Funobactam (XNW4107) is a novel serine β-lactamase inhibitor, belonging to the diazabicyclooctane (DBO) class [1]. It enhances the activity of carbapenem antibacterials against carbapenem-resistant strains of Acinetobacter baumannii and Klebsiella pneumoniae [1]. Funobactam is in clinical development in combination with imipenem + cilastatin for the treatment of complicated urinary tract infections (cUTIs) and hospital acquired/ventilator-associated bacterial pneumonia (HABP/VABP).

funobactam is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 179.89
Molecular weight 399.38
XLogP -1.9
No. Lipinski's rules broken 1

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
Click here for help

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/)

✖
Canonical SMILES C1CC12C[C@@H](C3=NN=C([C@@H]4CNC(=N4)N)O3)N5C[C@@H]2N(C5=O)OS(=O)(=O)O
Isomeric SMILES C1CC12C[C@H](N3C[C@@H]2N(C3=O)OS(=O)(=O)O)C4=NN=C(O4)[C@@H]5CNC(=N5)N
InChI InChI=1S/C13H17N7O6S/c14-11-15-4-6(16-11)9-17-18-10(25-9)7-3-13(1-2-13)8-5-19(7)12(21)20(8)26-27(22,23)24/h6-8H,1-5H2,(H3,14,15,16)(H,22,23,24)/t6-,7-,8-/m0/s1
InChI Key GRRBXZJDEZJMHA-FXQIFTODSA-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
Funobactam in combination with imipenem/cilastatin has advanced to Phase 3 evaluation as an intravenous treatment for cUTIs (NCT05204368) and HABP/VABP (NCT05204563).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05204368 Evaluation of the Efficacy and Safety of Intravenous Imipenem/Cilastatin/XNW4107 in Comparison With Meropenem in Hospitalized Adults With cUTI Including AP (EudraCT no. 2022-000061-40) Phase 3 Interventional Evopoint Biosciences Inc.
NCT05204563 Imipenem/Cilastatin-XNW4107 Versus Imipenem/Cilastatin/Relebactam for Treatment of Participants With Bacterial Pneumonia (XNW4107-302, REITAB-2) Phase 3 Interventional Evopoint Biosciences Inc.