aztreonam   Click here for help

GtoPdb Ligand ID: 10763

Synonyms: Azactam® | Cayston® | SQ 26776 | SQ-26776 | SQ26776
Approved drug
aztreonam is an approved drug (FDA (1986), EMA (2009))
Compound class: Synthetic organic
Comment: Aztreonam is a monocyclic β-lactam antibacterial that is resistant to β-lactamase hydrolysis. It was isolated from Chromobacterium violaceum. Functionally it preferentially binds to and inactivates penicillin-binding protein-3 (PBP-3) and thereby inhibits bacterial cell wall synthesis. Aztreonam was removed from the World Health Organization's List of Essential Medicines in 2019.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 238.2
Molecular weight 435.05
XLogP -1.26
No. Lipinski's rules broken 1
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Canonical SMILES C[C@H]1[C@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)C(=O)N1S(=O)(=O)O
Isomeric SMILES C[C@H]1[C@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1986), EMA (2009))
IUPAC Name Click here for help
2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
International Nonproprietary Names Click here for help
INN number INN
5159 aztreonam
Synonyms Click here for help
Azactam® | Cayston® | SQ 26776 | SQ-26776 | SQ26776
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Aztreonam + Avibactam | Aztreonam
Other databases
CAS Registry No. 78110-38-0 (source: PubChem)
DrugCentral Ligand 279
GtoPdb PubChem SID 405560204
PubChem CID 5742832
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UniChem Compound Search for chemical match using the InChIKey WZPBZJONDBGPKJ-VEHQQRBSSA-N
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