CHEBI:161680 - aztreonam

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ChEBI Name aztreonam
ChEBI ID CHEBI:161680
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41008, CHEBI:2960
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Formula C13H17N5O8S2
Net Charge 0
Average Mass 435.43300
Monoisotopic Mass 435.052
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
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
Roles Classification
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor
An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of peptidoglycan glycosyltransferase (EC 2.4.1.129).
antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing aztreonam (CHEBI:161680) has role antibacterial drug (CHEBI:36047)
aztreonam (CHEBI:161680) has role drug allergen (CHEBI:88188)
aztreonam (CHEBI:161680) has role EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor (CHEBI:50696)
aztreonam (CHEBI:161680) is a monobactam (CHEBI:50695)
Incoming aztreonyl-L-lysine (CHEBI:139368) has functional parent aztreonam (CHEBI:161680)
aztreonyl group (CHEBI:60429) is substituent group from aztreonam (CHEBI:161680)
IUPAC Name
(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
INNs Sources
aztreonam ChEBI
aztréonam ChEBI
aztreonamum ChemIDplus
Synonyms Sources
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid ChemIDplus
AZT ChEBI
Brand Names Sources
Azactam DrugBank
Primbactam DrugBank
Manual Xrefs Databases
279 DrugCentral
AZR PDBeChem
Aztreonam Wikipedia
C06840 KEGG COMPOUND
D00240 KEGG DRUG
DB00355 DrugBank
NL8100571 Patent
View more database links
Registry Numbers Types Sources
3577211 Beilstein Registry Number Beilstein
3577211 Reaxys Registry Number Reaxys
78110-38-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1384868 PubMed citation Europe PMC
15123864 PubMed citation Europe PMC
24119095 PubMed citation Europe PMC
24176390 PubMed citation Europe PMC
24369293 PubMed citation Europe PMC
25049240 PubMed citation Europe PMC
25091537 PubMed citation Europe PMC
25295210 PubMed citation Europe PMC
28543395 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
Last Modified
14 March 2018