sulbactam
CHEBI:9321
·resolve ·ANTIMICROBIAL_UNSPECIFIED
·EXACT
REVIEWED
Classification
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
SMILES
[H][C@@]12CC(=O)N1[C@@H](C(=O)O)C(C)(C)S2(=O)=O
InChI
InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
Also called
- sulbactamum (INN)— chebi
- 2,2-dimethyl-1,1-dioxidopenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
- (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxide (EXACT_SYNONYM)— chebi
- (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide (EXACT_SYNONYM)— chebi
- CP 45899 (EXACT_SYNONYM)— chebi
- CP-45899 (EXACT_SYNONYM)— chebi
- CP45899 (EXACT_SYNONYM)— chebi
- penicillanic acid 1,1-dioxide (EXACT_SYNONYM)— chebi
- penicillanic acid sulfone (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.
engineered S70C SHV-1 beta-lactamase PROTEIN DIRECT_BINDING_TARGET
A 1.45-angstrom cocrystal captured intact sulbactam in the active site of S70C SHV-1; the engineered catalytic mutation and C70-K73 sulfenamide bond limit extrapolation to wild-type enzyme. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2012-09 (retrieved 2026-09-02).
- PMID:22974281 (Primary sulbactam-S70C-SHV-1 preacylation structure (DOI:10.1021/ja3073676).)
Mechanism summary
- Mode of action
- OTHER microbial target — CURATOR: PMID:22974281 resolved intact sulbactam in a 1.45-angstrom preacylation complex with an engineered S70C SHV-1 beta-lactamase. The mutation and an unexpected C70-K73 sulfenamide bond were used to trap the otherwise reactive complex, so this structure establishes inhibitor recognition but is not a wild-type preacylation structure.
Record-level evidence
- PMID:22974281 (Primary exact-sulbactam preacylation cocrystal in an engineered SHV-1 beta-lactamase.)
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 ChEBI identity, structure, antibiotic role, and unspecified filing class; added beta-lactamase inhibition and the directly observed engineered-SHV-1 complex with its mutant-context limitation.
-
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/.
View the record (YAML).
Explore across X-Mech:
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