Compound ID | 1874

Update compound information

Avibactam (Avycaz, Zavicefta)

Synonym(s): NXL104  |  AVE1330A

Class: Beta-lactamase inhibitor

Agent Type: Synthetic; Small molecule; Direct acting; Antibiotic adjuvant;
Mechanism of action: Binds reversibly to the beta-lactamase in the active site; inhibits class A, C, D beta-lactamases
Combined with other compounds: Yes
Description: Synthetic compound. 2015 approved in fixed combination with ceftazidime. Orally available prodrug in clinical development, fixed combination with aztreonam in clinical development; a non-beta-lactam beta-lactamase inhibitor, diazabicyclooctane (DBO); no intrinsic antibacterial activity
Institute where first reported: Sanofi-Aventis, Novexel, AstraZeneca, Pfizer, Abbvie (formerly Actavis, Allergan, Forest Laboratories)
Year first mentioned: 2002
Highest development stage: Approved by FDA in 2015
Development status: Approved
Chemical structure(s):
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Molecular weight: 265.25
Iso. SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)N
InChI Key: NDCUAPJVLWFHHB-UHNVWZDZSA-N
Can. SMILES: C1C[C@@H](C(=O)N)N2C[C@@H]1N(C2=O)OS(=O)(=O)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9835049
Guide to Pharmacology: avibactam
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/32285965/
  • https://www.mdpi.com/2079-6382/10/8/1012/htm
  • https://www.thelancet.com/journals/laninf/article/PIIS1473-3099(16)30194-3/fulltext
  • https://pubmed.ncbi.nlm.nih.gov/15254025/

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