avibactam
CHEBI:85984
·resolve ·ANTIBACTERIAL
·EXACT
REVIEWED
A member of the class of azabicycloalkanes that is (2S,5R)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide in which the amino hydrogen at position 6 is replaced by a sulfooxy group. Used (in the form of its sodium salt) in combination with ceftazidime pentahydrate for the treatment of complicated urinary tract infections including pyelonephritis. — ChEBI
Classification
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
SMILES
NC(=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=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
Also called
- (2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (EXACT_SYNONYM)— chebi
- NXL 104 (EXACT_SYNONYM)— chebi
- NXL104 (EXACT_SYNONYM)— chebi
Cross-references
Identifiers for this same structure in other resources. An
accession that lands on two different structures in this corpus is withheld from
both rather than shown here, since it names at most one of them.
Drug registries
Identifiers that name a drug rather than a structure. One of
these can cover a parent compound, its salts and its stereoisomers, which this
corpus keeps as separate records, so it is not an equivalence of structure.
Patents and articles
Documents about this compound. A patent covers a class and an
article covers a topic; neither identifies a structure.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
Source concepts
Every upstream concept that resolved to this record. The merge is
the product: this is what shows ChEBI and CARD are describing the same structure.
Molecular targets
The molecular entity or process this compound acts on. Each target
carries evidence — this is a mechanistic claim, not a classification.
class D OXA beta-lactamases PROTEIN DIRECT_BINDING_TARGET
X-ray structures of OXA-24 and OXA-48 captured covalent inhibited states and, together with kinetic analysis, explained selective, slowly reversible beta-lactamase inhibition. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2014-12 (retrieved 2026-09-02).
- PMID:25406838 (Primary avibactam-bound OXA-24/OXA-48 structural and kinetic study (DOI:10.1021/cb500703p).)
Mechanism summary
- Mode of action
- OTHER microbial target — CURATOR: PMID:25406838 resolved covalent avibactam complexes with the class D beta-lactamases OXA-24 and OXA-48 and explained the inhibitor's selectivity and unusually slow reversibility. Avibactam restores partner beta-lactam activity by inhibiting resistance enzymes rather than by directly inhibiting bacterial cell-wall synthesis itself.
Record-level evidence
- PMID:25406838 (Primary class D beta-lactamase inhibition and cocrystal study.)
Curation history
-
SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
REVIEWED
2026-09-02 · codex · LLM-assisted
Verified exact neutral avibactam ChEBI identity distinct from its sodium form, structure, roles, and antibacterial filing class; added the resistance-enzyme mechanism and directly bound OXA beta-lactamase target.
-
RESEEDED_FROM_SOURCES
2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
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