taniborbactam   Click here for help

GtoPdb Ligand ID: 10774

Synonyms: VNRX-5133 | VNRX5133
PDB Ligand
Compound class: Synthetic organic
Comment: Taniborbactam (VNRX-5133) is a clinical stage, injectable, broad-spectrum β-lactamase inhibitor [1,3]. It has activity against both serine- and metallo-β-lactamases (e.g. oxacillinase, Klebsiella pneumoniae carbapenemase, New Delhi metallo-beta-lactamase, Verona integron-encoded metallo-beta-lactamase and extended spectrum beta-lactamase) [4]. Taniborbactam will be administered alongside the cephalosporin antibacterial cefepime. It is being developed by Venatorx Pharmaceuticals in partnership with the Global Antibiotic Research & Development Partnership (GARDP).
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 7
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 133.91
Molecular weight 389.21
XLogP 1.19
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 NCCNC1CCC(CC1)CC(=O)N[C@H]1Cc2cccc(c2OB1O)C(=O)O
Isomeric SMILES NCCNC1CCC(CC1)CC(=O)N[C@H]1Cc2cccc(c2OB1O)C(=O)O
InChI InChI=1S/C19H28BN3O5/c21-8-9-22-14-6-4-12(5-7-14)10-17(24)23-16-11-13-2-1-3-15(19(25)26)18(13)28-20(16)27/h1-3,12,14,16,22,27H,4-11,21H2,(H,23,24)(H,25,26)/t12?,14?,16-/m0/s1
InChI Key PFZUWUXKQPRWAL-PXCJXSSVSA-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/)
References
1. Bakthavatchalam YD, Elangovan D, Jaganathan SV, Subburaju N, Shankar A, Manokaran Y, J S, Devi R, Baveja S, Devi S et al.. (2023)
In Vitro Activity of Two Cefepime-Based Novel Combinations, Cefepime/Taniborbactam and Cefepime/Zidebactam, against Carbapenemase-Expressing Enterobacterales Collected in India.
Microbiol Spectr, 11 (2): e0492522 [Epub ahead of print]. [PMID:36847537]
2. Dowell JA, Marbury TC, Smith WB, Henkel T. (2022)
Safety and Pharmacokinetics of Taniborbactam (VNRX-5133) with Cefepime in Subjects with Various Degrees of Renal Impairment.
Antimicrob Agents Chemother, 66 (9): e0025322. [PMID:35920662]
3. Karvouniaris M, Almyroudi MP, Abdul-Aziz MH, Blot S, Paramythiotou E, Tsigou E, Koulenti D. (2023)
Novel Antimicrobial Agents for Gram-Negative Pathogens.
Antibiotics (Basel), 12 (4). [PMID:37107124]
4. Krajnc A, Brem J, Hinchliffe P, Calvopiña K, Panduwawala TD, Lang PA, Kamps JJAG, Tyrrell JM, Widlake E, Saward BG et al.. (2019)
Bicyclic Boronate VNRX-5133 Inhibits Metallo- and Serine-β-Lactamases.
J Med Chem, 62 (18): 8544-8556. [PMID:31454231]
5. Moeck G, Gasink LB, Mendes RE, Woosley LN, Dorr M, Chen H, Wagenlehner FM, Henkel T, McGovern PC. (2024)
Patient outcomes by baseline pathogen resistance phenotype and genotype in CERTAIN-1, a Phase 3 study of cefepime-taniborbactam versus meropenem in adults with complicated urinary tract infection.
Antimicrob Agents Chemother, 68 (7): e0023624. [PMID:38780262]
6. Wagenlehner FM, Gasink LB, McGovern PC, Moeck G, McLeroth P, Dorr M, Dane A, Henkel T, CERTAIN-1 Study Team. (2024)
Cefepime-Taniborbactam in Complicated Urinary Tract Infection.
N Engl J Med, 390 (7): 611-622. [PMID:38354140]