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.
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 6
Topological polar surface area 124.1
Molecular weight 297.08
XLogP 0.33
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 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
References
1. Bhowmick T. (2021)
Clinical Outcomes of Patient Subgroups in the TANGO II Study.
Infect Dis Ther, 10 (1): 35-46. [PMID:33565042]
2. Dhillon S. (2018)
Meropenem/Vaborbactam: A Review in Complicated Urinary Tract Infections.
Drugs, 78 (12): 1259-1270. [PMID:30128699]
3. Hecker SJ, Reddy KR, Totrov M, Hirst GC, Lomovskaya O, Griffith DC, King P, Tsivkovski R, Sun D, Sabet M et al.. (2015)
Discovery of a Cyclic Boronic Acid β-Lactamase Inhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases.
J Med Chem, 58 (9): 3682-92. [PMID:25782055]
4. Jorgensen SCJ, Rybak MJ. (2018)
Meropenem and Vaborbactam: Stepping up the Battle against Carbapenem-resistant Enterobacteriaceae.
Pharmacotherapy, 38 (4): 444-461. [PMID:29427523]
5. Kaye KS, Bhowmick T, Metallidis S, Bleasdale SC, Sagan OS, Stus V, Vazquez J, Zaitsev V, Bidair M, Chorvat E et al.. (2018)
Effect of Meropenem-Vaborbactam vs Piperacillin-Tazobactam on Clinical Cure or Improvement and Microbial Eradication in Complicated Urinary Tract Infection: The TANGO I Randomized Clinical Trial.
JAMA, 319 (8): 788-799. [PMID:29486041]
6. Wunderink RG, Giamarellos-Bourboulis EJ, Rahav G, Mathers AJ, Bassetti M, Vazquez J, Cornely OA, Solomkin J, Bhowmick T, Bishara J et al.. (2018)
Effect and Safety of Meropenem-Vaborbactam versus Best-Available Therapy in Patients with Carbapenem-Resistant Enterobacteriaceae Infections: The TANGO II Randomized Clinical Trial.
Infect Dis Ther, 7 (4): 439-455. [PMID:30270406]