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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16BNO5S
Molecular Weight 297.135
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VABORBACTAM

SMILES

OB1O[C@H](CC(O)=O)CC[C@@H]1NC(=O)CC2=CC=CS2

InChI

InChIKey=IOOWNWLVCOUUEX-WPRPVWTQSA-N
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

HIDE SMILES / InChI

Description

Vaborbactam (formerly RPX7009) is a new beta-lactamase inhibitor based on a cyclic boronic acid pharmacophore. Vaborbactam is a highly active beta-lactamase inhibitor that restores activity of meropenem and other beta-lactam antibiotics in beta-lactamase-producing bacteria, particularly KPC-producing CRE. Meropenem in combination with vaborbactam (VABOMERE) is indicated for the treatment of patients 18 years and older with complicated urinary tract infections including pyelonephritis caused by designated susceptible bacteria. The vaborbactam component of VABOMERE is a non-suicidal beta-lactamase inhibitor that protects meropenem from degradation by certain serine beta-lactamases such as Klebsiella pneumoniae carbapenemase (KPC). Vaborbactam does not have any antibacterial activity. Vaborbactam does not decrease the activity of meropenem against meropenem-susceptible organisms.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
VABOMERE
PubMed

PubMed

TitleDatePubMed
Effect of the β-Lactamase Inhibitor Vaborbactam Combined with Meropenem against Serine Carbapenemase-Producing Enterobacteriaceae.
2016 Sep
Vaborbactam: Spectrum of Beta-Lactamase Inhibition and Impact of Resistance Mechanisms on Activity in Enterobacteriaceae.
2017 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Administer VABOMERE 4 grams (meropenem 2 grams and vaborbactam 2 grams) every 8 hours by intravenous infusion over 3 hours for up to 14 days, in patients 18 years of age and older with an estimated glomerular filtration rate (eGFR) ≥50 mL/min/1.73m2 Dosage adjustment is recommended in patients with renal impairment who have an eGFR less than 50 mL/min/ 1.73m2
Route of Administration: Intravenous
In Vitro Use Guide
The activity of meropenem combined with the serine β-lactamase inhibitor vaborbactam (formerly RPX7009) was studied against 315 serine carbapenemase-producing Enterobacteriaceae (CPE) isolates by use of checkerboard-designed panels to assess the optimal inhibitor concentration (range tested, 0.5 to 32 μg/ml). Overall, meropenem alone (MIC50 and MIC90, 16 and >64 μg/ml, respectively) inhibited only 2.2% of the isolates at ≤1 μg/ml (the CLSI susceptibility breakpoint) and 7.3% of the isolates at ≤2 μg/ml (the EUCAST breakpoint). Vaborbactam restored meropenem activity for 72.7 to 98.1% of CPE isolates at ≤2 μg/ml, and maximum potentiation was achieved with fixed concentrations of ≥8 μg/ml of the inhibitor (≥96.5% of isolates were inhibited at ≤2 μg/ml of meropenem-vaborbactam). Meropenem-vaborbactam with a fixed concentration of 8 μg/ml of the inhibitor (MIC50, ≤0.06 μg/ml for all organisms) inhibited 93.7% of the CPE isolates displaying elevated meropenem MICs at ≤1 μg/ml. Meropenem-vaborbactam MICs were elevated for isolates producing metallo-β-lactamases (MIC, 16 to >64 μg/ml) or displaying decreased expression of OmpK37 and/or elevated expression of the AcrAB-TolC efflux system (MIC, 16 μg/ml). Vaborbactam showed no antibacterial activity alone (all MICs, >64 μg/ml).
Name Type Language
VABORBACTAM
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
VABORBACTAM [USAN]
Common Name English
RPX-7009
Code English
1,2-OXABORINANE-6-ACETIC ACID, 2-HYDROXY-3-((2-(2-THIENYL)ACETYL)AMINO)-, (3R,6S)-
Systematic Name English
RPX7009
Code English
CARBAVANCE COMPONENT VABORBACTAM
Brand Name English
VABORBACTAM COMPONENT OF CARBAVANCE
Brand Name English
VABORBACTAM [WHO-DD]
Common Name English
VABOMERE COMPONENT VABORBACTAM
Brand Name English
VABORBACTAM [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
WHO-ATC J01DH52
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
NDF-RT N0000175930
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
Code System Code Type Description
INN
10182
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
PRIMARY
NCI_THESAURUS
C152810
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
PRIMARY
CAS
1575712-03-6
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
NO STRUCTURE GIVEN
PUBCHEM
56649692
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
PRIMARY
CAS
1360457-46-0
Created by admin on Mon Oct 21 19:46:13 UTC 2019 , Edited by admin on Mon Oct 21 19:46:13 UTC 2019
PRIMARY