aztreonam   Click here for help

GtoPdb Ligand ID: 10763

Synonyms: Azactam® | Cayston® | Emblaveo® (aztreonam and avibactam) | 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.

aztreonam is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Aztreonam is used as a single agent to treat serious infections 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 was investigated in an intravenous fixed-dose combination with the β-lactamase inhibitor avibactam (ATM-AVI; PF-06947387) for the treatment of serious bacterial infections. This formulation (Emblaveo®) was approved by the EMA in April 2024 to treat infections that are caused by susceptible bacteria.
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
External links Click here for help
For extended ADME data see the following:

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