U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16BNO5S
Molecular Weight 297.1367
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VABORBACTAM

SMILES

c1cc(CC(=N[C@@]2([H])CC[C@@]([H])(CC(=O)O)OB2O)O)sc1

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
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
Curative
VABOMERE

Approved Use

VABOMERE (meropenem and vaborbactam) is a combination of meropenem, a penem antibacterial, and vaborbactam, a beta-lactamase inhibitor, indicated for the treatment of patients 18 years and older with complicated urinary tract infections (cUTI) including pyelonephritis caused by designated susceptible bacteria.

Launch Date

1.50387845E12
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
33.4 μg/mL
1500 mg 3 times / day multiple, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
40.9 μg/mL
2000 mg 3 times / day multiple, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.81 μg/mL
250 mg 3 times / day multiple, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.3 μg/mL
1000 mg 3 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
27.8 μg/mL
1250 mg single, intravenous
dose: 1250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
32.9 μg/mL
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
41.6 μg/mL
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.03 μg/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.97 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
15.3 μg/mL
750 mg single, intravenous
dose: 750 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.8 μg/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
118 μg × h/mL
1500 mg 3 times / day multiple, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
145 μg × h/mL
2000 mg 3 times / day multiple, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.3 μg × h/mL
250 mg 3 times / day multiple, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
74.6 μg × h/mL
1000 mg 3 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
100 μg × h/mL
1250 mg single, intravenous
dose: 1250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
114 μg × h/mL
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
144 μg × h/mL
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.6 μg × h/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
35.6 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
51.8 μg × h/mL
750 mg single, intravenous
dose: 750 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
79.3 μg × h/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.65 h
1500 mg 3 times / day multiple, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.66 h
2000 mg 3 times / day multiple, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.17 h
250 mg 3 times / day multiple, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.43 h
1000 mg 3 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.32 h
1250 mg single, intravenous
dose: 1250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.4 h
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.51 h
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.17 h
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.35 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.24 h
750 mg single, intravenous
dose: 750 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.41 h
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
67%
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VABORBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day for 2 days)
Sources: Page: 2017/209776Orig1s000ClinPharmR.pdf - p.132
healthy, adult
n = 26
Health Status: healthy
Age Group: adult
Population Size: 26
Sources: Page: 2017/209776Orig1s000ClinPharmR.pdf - p.132
Disc. AE: Chest discomfort...
AEs leading to
discontinuation/dose reduction:
Chest discomfort (3.8%)
Sources: Page: 2017/209776Orig1s000ClinPharmR.pdf - p.132
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
Disc. AE: Pyrexia, Drug hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Pyrexia (0.3%)
Drug hypersensitivity (0.3%)
Hypersensitivity (0.3%)
Septic shock (0.3%)
Infusion related reaction (0.7%)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
2 g 3 times / day multiple, intravenous
Highest studied dose|Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day for 5 days)
Sources: Page: 209776Orig1s000ClinPharmR.pdf - p.147
unhealthy
Health Status: unhealthy
Sources: Page: 209776Orig1s000ClinPharmR.pdf - p.147
AEs

AEs

AESignificanceDosePopulation
Chest discomfort 3.8%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day for 2 days)
Sources: Page: 2017/209776Orig1s000ClinPharmR.pdf - p.132
healthy, adult
n = 26
Health Status: healthy
Age Group: adult
Population Size: 26
Sources: Page: 2017/209776Orig1s000ClinPharmR.pdf - p.132
Drug hypersensitivity 0.3%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
Hypersensitivity 0.3%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
Pyrexia 0.3%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
Septic shock 0.3%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
Infusion related reaction 0.7%
Disc. AE
2 g 3 times / day multiple, intravenous
Recommended
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Meropenem(2 g; 3 per day up to 14 days)
Sources: Page: 209776Orig1s000MedR.pdf - p.192
unhealthy, adult
n = 295
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 295
Sources: Page: 209776Orig1s000MedR.pdf - p.192
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
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

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
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
VABORBACTAM [ORANGE BOOK]
Common Name 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
VABORBACTAM [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
WHO-ATC J01DH52
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
NDF-RT N0000175930
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
Code System Code Type Description
DRUG CENTRAL
5253
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
INN
10182
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
DRUG BANK
DB12107
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
NCI_THESAURUS
C152810
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
FDA UNII
1C75676F8V
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
CAS
1575712-03-6
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
NO STRUCTURE GIVEN
MERCK INDEX
M12030
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
RXCUI
1945213
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
PUBCHEM
56649692
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY
CAS
1360457-46-0
Created by admin on Sat Jun 26 11:01:53 UTC 2021 , Edited by admin on Sat Jun 26 11:01:53 UTC 2021
PRIMARY