Avibactam

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Avibactam structure 2.svg
200px
Systematic (IUPAC) name
[(2S,5R)-2-Carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
Clinical data
Trade names Avycaz (formulated with ceftazidime)
Pregnancy
category
  • US: B (No risk in non-human studies)
Legal status
Routes of
administration
IV
Pharmacokinetic data
Bioavailability 100% (intravenous)
Protein binding 5.7–8.2%[1]
Metabolism Nil
Onset of action Increases in proportion to dose
Excretion Renal (97%)
Identifiers
CAS Number 1192500-31-4
ATC code None
PubChem CID: 9835049
ChemSpider 8010770
KEGG D10340
ChEBI CHEBI:85984 YesY
ChEMBL CHEMBL1689063
Chemical data
Formula C7H11N3O6S
Molecular mass 265.24 g/mol
  • [C@]12C[N@]([C@@H](CC1)C(N)=O)C(=O)N2OS(O)(=O)=O
  • InChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1
  • Key:NDCUAPJVLWFHHB-UHNVWZDZSA-N

Avibactam is a non-β-lactam β-lactamase inhibitor antibiotic developed by Actavis (now Allergan) jointly with AstraZeneca. A new drug application for avibactam in combination with ceftazidime was approved by the FDA on February 25, 2015, for treating complicated urinary tract (cUTI) and complicated intra-abdominal infections (cIAI) caused by antibiotic resistant-pathogens, including those caused by multi-drug resistant Gram-negative bacterial pathogens.[2][3][4]

Increasing resistance to cephalosporins among Gram-(−) bacterial pathogens, especially among hospital-acquired infections, results in part from the production of β-lactamase enzymes that deactivate these antibiotics. While the co-administration of a β-lactamase inhibitor can restore antibacterial activity to the cephalosporin, previously approved β-lactamase inhibitors such as tazobactam and clavulanic acid do not inhibit important classes of β-lactamases, including Klebsiella pneumoniae carbapenemases (KPCs), New Delhi metallo-β-lactamase 1 (NDM-1), and AmpC-type β-lactamases. Avibactam inhibits KPCs, AmpC, and some Class D β-lactamases, but is not active against NDM-1.[5]

References

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External links

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