4D6

Vaborbactam

Created: 2015-03-03
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count36
Chiral Atom Count2
Bond Count37
Aromatic Bond Count5
2D diagram of 4D6
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Chemical Component Summary

NameVaborbactam
Synonyms2-((3R,6S)-2-hydroxy-3-(2-(thiophen-2-yl)acetamido)-1,2-oxaborinan-6-yl)acetic acid; 2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid; 1,2-Oxaborinane-6-acetic acid, 2-hydroxy-3-((2-(2-thienyl)acetyl)amino)-, (3R,6S)-; 56649692; CHEMBL3317857; {(3R,6S)-2-hydroxy-3-[(thiophen-2-ylacetyl)amino]-1,2-oxaborinan-6-yl}acetic acid; DB12107
Systematic Name (OpenEye OEToolkits)2-[(3R,6S)-2-oxidanyl-3-(2-thiophen-2-ylethanoylamino)-1,2-oxaborinan-6-yl]ethanoic acid
FormulaC12 H16 B N O5 S
Molecular Weight297.135
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01c2ccc(CC(NC1CCC(OB1O)CC(=O)O)=O)s2
SMILESCACTVS3.385OB1O[CH](CC[CH]1NC(=O)Cc2sccc2)CC(O)=O
SMILESOpenEye OEToolkits1.9.2B1(C(CCC(O1)CC(=O)O)NC(=O)Cc2cccs2)O
Canonical SMILESCACTVS3.385 OB1O[C@@H](CC[C@@H]1NC(=O)Cc2sccc2)CC(O)=O
Canonical SMILESOpenEye OEToolkits1.9.2 B1([C@H](CC[C@H](O1)CC(=O)O)NC(=O)Cc2cccs2)O
InChIInChI1.03 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
InChIKeyInChI1.03 IOOWNWLVCOUUEX-WPRPVWTQSA-N

Drug Info: DrugBank

DrugBank IDDB12107 
NameVaborbactam
Groups
  • approved
  • investigational
DescriptionVaborbactam is a β-lactamase inhibitor based on a cyclic boronic acid pharmacophore.[A32053] 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.[Label] 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.
SynonymsVaborbactam
Brand Names
  • Vabomere
  • Vaborem
IndicationIndicated in combination with meropenem for the treatment of patients 18 years of age and older with complicated urinary tract infections (cUTI) including pyelonephritis caused by the following susceptible microorganisms: _Escherichia coli_, _Klebsiella pneumoniae_, and _Enterobacter cloacae_ species complex.[FDA Label]
Categories
  • Acids
  • Acids, Noncarboxylic
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DH52
CAS number1360457-46-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Beta-lactamaseMMRKSLCCALLLGISCSALATPVSEKQLAEVVANTITPLMKAQSVPGMAV...unknowninhibitor
Carbapenem-hydrolyzing beta-lactamase KPCMSLYRRLVLLSCLSWPLAGFSATALTNLVAEPFAKLEQDFGGSIGVYAMD...unknowninhibitor
Beta-lactamase (KPC-2)MSLYRRLVLLSCLSWPLAGFSATALTNLVAEPFAKLEQDFGGSIGVYAMD...unknowninhibitor
Beta-lactamase CTX-MMVTKRVQRMMFAAAACIPLLLGSAPLYAQTSAVQQKLAALEKSSGGRLGV...unknowninhibitor
Beta-lactamase (blaSHV)GLTAFLRQIGDNVTRLDRWETELNEALPGDARDTTTPASMAATLRKLLTS...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 56649692
ChEMBL CHEMBL3317857