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Vaborbactam

CAT: 0804-HY-19930-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-19930-01Size:1 mg
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Description
Vaborbactam (RPX7009) is a cyclic boronic acid pharmacophore β-lactamase inhibitor.
CAS Number
1360457-46-0
Product Name Alternative
RPX7009
UNSPSC
12352005
Hazard Statement
H302, H312, H332
Target
Bacterial; Beta-lactamase
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/Vaborbactam.html
Purity
99.85
Solubility
H2O : 5.26 mg/mL (ultrasonic)
Smiles
O=C(O)C[C@@H]1CC[C@H](NC(CC2=CC=CS2)=O)B(O)O1
Molecular Formula
C12H16BNO5S
Molecular Weight
297.14
Precautions
H302, H312, H332
References & Citations
[1]Hecker SJ, et al. Discovery of a Cyclic Boronic Acid β-Lactamase Inhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases. J Med Chem. 2015 May 14;58 (9) :3682-92.|[2]Castanheira M, et al. Effect of the β-Lactamase Inhibitor Vaborbactam Combined with SM 7338 against Serine Carbapenemase-Producing Enterobacteriaceae. Antimicrob Agents Chemother. 2016 Aug 22;60 (9) :5454-8.|[3]Wong D, et al. Novel Beta-Lactamase Inhibitors: Unlocking Their Potential in Therapy.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Vaborbactam

Vaborbactam is a β-lactamase inhibitor based on a cyclic boronic acid pharmacophore. It has been used in trials investigating the treatment of bacterial infections in subjects with varying degrees of renal insufficiency. In August 2017, a combination antibacterial therapy under the market name Vabomere was approved by the FDA for the treatment of adult patients with complicated urinary tract infections (cUTI). Vabomere consists of vaborbactam and [Meropenem] for intravenous administration. Vaborbactam is added to the therapy to reduce the extent meropenem degradation by inhibiting the serine beta-lactamases expressed by the microorganism of target. The treatment aims to resolve infection-related symptoms of cUTI and achieve negative urine culture, when the infections are proven or strongly suspected to be caused by susceptible bacteria.

CAS Number1360457-46-0
PubChem CID56649692
IUPAC Name2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid
Molecular FormulaC12H16BNO5S
Molecular Weight297.14
Topological Polar Surface Area124
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Heavy Atom Count20
Formal Charge0
Complexity370
SMILES
B1([C@H](CC[C@H](O1)CC(=O)O)NC(=O)CC2=CC=CS2)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
InChIKey
IOOWNWLVCOUUEX-WPRPVWTQSA-N
Chemical Structure
2D Structure
2D structure of Vaborbactam
CAS: 1360457-46-0
CID: 56649692
Formula: C12H16BNO5S
MW: 297.14
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight297.14
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass297.0842240
Monoisotopic Mass297.0842240
Topological Polar Surface Area124 Ų
Heavy Atom Count20
Formal Charge0
Complexity370
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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