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 antibiotic 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
SMILES / InChI / InChIKey
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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
InChI Key WZPBZJONDBGPKJ-VEHQQRBSSA-N
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Summary of Clinical Use Click here for help
Aztreonam is used as a single agent to treat serious infevtions that are caused by susceptible gram-negative bacteria e.g. Citrobacter (including C. freundii), Enterobacter (including E. cloacae), E. coli, Klebsiella (including K. pneumoniae), Pseudomonas aeruginosa, or Serratia (including S. marcescens). In the EU, aztreonam (Cayston®) is indicated for the suppressive therapy of chronic pulmonary Pseudomonas aeruginosa infections in cystic fibrosis patients.Aztreonam is being investigated in an intravenous fixed-dose combination with the β-lactamase inhibitor avibactam (ATM-AVI; PF-06947387) for the treatment of serious bacterial infections.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03580044 Efficacy, Safety, and Tolerability of ATM-AVI in the Treatment of Serious Infection Due to MBL-producing Gram-negative Bacteria Phase 3 Interventional Pfizer
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