aztreonam

CHEBI:161680 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A synthetic monocyclic β-lactam antibiotic (monobactam), used primarily to treat infections caused by Gram-negative bacteria. It inhibits mucopeptide synthesis in the bacterial cell wall, thereby blocking peptidoglycan crosslinking. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

monobactamARO:0000004

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:50695 CHEBI:50695
CHEBI:88225 CHEBI:88225
ARO:0000004 ARO:0000004

Chemical structure

Computed structure properties
Molecular formula	C13H17N5O8S2
Charge	0
Average mass	435.44 Da
Monoisotopic mass	435.05185 Da
Source	ChEBI
InChIKey	WZPBZJONDBGPKJ-VEHQQRBSSA-N

SMILES

C[C@H]1[C@H](NC(=O)/C(=N\OC(C)(C)C(=O)O)c2csc([NH3+])n2)C(=O)N1S(=O)(=O)[O-]

InChI

InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1

Also called

Azactam (BRAND_NAME)— chebi
Primbactam (BRAND_NAME)— chebi
aztreonamum (INN)— chebi
aztréonam (INN)— chebi
(2S,3S)-3-{(2Z)-2-(2-ammonio-1,3-thiazol-4-yl)-2-[(2-carboxypropan-2-yloxy)imino]acetamido}-2-methyl-4-oxoazetidine-1-sulfonate (EXACT_SYNONYM)— chebi
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid (EXACT_SYNONYM)— chebi
AZT (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000550
beilstein:3577211
cas:78110-38-0
drugbank:DB00355
drugcentral:279
kegg.compound:C06840
kegg.drug:D00240
patent:NL8100571
pdb-ccd:AZR
reaxys:3577211
wikipedia.en:Aztreonam
chembl:CHEMBL158
pubchem.compound:5742832

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000550`	aztreonam	`antibioticmech:aro-51d3653044`	2026-08-30
CHEBI	`CHEBI:161680`	aztreonam	`antibioticmech:chebi-2c259cb7a2`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

7 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 4

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACC-1	ARO:3001815	not organism-specific	—	ARO:3001815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)
ACC-4	ARO:3001818	not organism-specific	—	ARO:3001818 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)
TEM-61	ARO:3000930	not organism-specific	—	ARO:3000930 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)
VCC-1	ARO:3003713	not organism-specific	—	ARO:3003713 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
MexAB-OprM	ARO:3000386	not organism-specific	—	ARO:3000386 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)
MuxABC-OpmB	ARO:3004076	not organism-specific	—	ARO:3004076 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Pseudomonas aeruginosa ampR with mutation conferring resistance to aztreonam	ARO:3007491	not organism-specific	—	ARO:3007491 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000550 (aztreonam); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · 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.