avibactam

Also known as NXL 104, NXL104

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

Key facts

Drug.IUPAC_name: [(2S,5R)-2-Carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
Drug.image: Avibactam structure 2.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Avibactam ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.tradename: Avycaz (formulated with ceftazidime)
Drug.routes_of_administration: Intravenous therapy
Drug.legal_US: Rx-only
Drug.bioavailability: 100% (intravenous)
Drug.protein_bound: 5.7–8.2%
Drug.metabolism: Nil
Drug.onset: Increases in proportion to dose
Drug.excretion: Kidney (97%)
Drug.CAS_number: 1192500-31-4
Drug.UNII: 7352665165
Drug.ATC_prefix: None
Drug.PubChem: 9835049

via Wikipedia infobox

Chemical data

Formula: C7H11N3O6S
Molecular weight: 265.25 g/mol
IUPAC name: [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)N
InChIKey: NDCUAPJVLWFHHB-UHNVWZDZSA-N
XLogP: -1.8
Polar surface area: 139 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2015
Admin. routes: parenteral
Indications: infection, urinary tract infection, pneumonia, systemic inflammatory response syndrome

via ChEMBL · EBI

Research

3,137 papers

Aztreonam-avibactam: The dynamic duo against multidrug-resistant gram-negative pathogens.Pharmacotherapy · 2024
Aztreonam and avibactam combination therapy for metallo-β-lactamase-producing gram-negative bacteria: A Narrative Review.Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases · 2025
Avibactam Pharmacokinetic/Pharmacodynamic Targets.Antimicrobial agents and chemotherapy · 2018
Population pharmacokinetic/pharmacodynamic modeling to optimize aztreonam-avibactam dose regimens for adult patients.Antimicrobial agents and chemotherapy · 2025
Past, present, and future perspectives on aztreonam and avibactam.Expert review of anti-infective therapy · 2025

via PubMed

Wikidata facts

Mass: 265.036856
Has use: medication

Show 5 more facts

chemical formula: C₇H₁₁N₃O₆S
canonical SMILES: C1CC(N2CC1N(C2=O)OS(=O)(=O)O)C(=O)N
isomeric SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)N
Commons category: Avibactam
subject has role: bactericide

Sources (3)

via Wikidata · CC0

~2 min read

Encyclopedic overview

2 sections

Contents

References
Further reading

Increasing resistance to cephalosporins among Gram-negative 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. Whilst avibactam inhibits class A (KPCs, CTX-M, TEM, SHV), class C (AmpC), and some class D serine β-lactamases (such as OXA-23, OXA-48), it has been reported to be a poor substrate/weak inhibitor of class B metallo-β-lactamases, such as VIM-2, VIM-4, SPM-1, BcII, NDM-1, Fez-1.

Excerpted from Wikipedia’s “avibactam” article, available under the CC BY-SA 4.0 licence.

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