Aztreonam

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

Aztreonam
Clinical data
Trade namesAzactam, Cayston, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous, intramuscular, inhalation
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability100% (IM) 0.1% (by mouth in rats) Unknown (by mouth in humans)
Protein binding56%
MetabolismLiver (minor %)
Elimination half-life1.7 hours
ExcretionKidney
Identifiers
  • 2-{[(1Z)-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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.071.652
Chemical and physical data
FormulaC13H17N5O8S2
Molar mass435.43 g·mol−1
3D model (JSmol)
Melting point227 °C (441 °F) (dec.)
SMILES
  • O=S(=O)(O)N2C(=O)[C@@H](NC(=O)C(=N\OC(C(=O)O)(C)C)/c1nc(sc1)N)[C@@H]2C
  • 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 Y
  • Key:WZPBZJONDBGPKJ-VEHQQRBSSA-N Y
  (verify)

Common side effects when given by injection include pain at the site of injection, vomiting, and rash. Common side effects when inhaled include wheezing, cough, and vomiting. Serious side effects include Clostridium difficile infection and allergic reactions including anaphylaxis. Those who are allergic to other β-lactam have a low rate of allergy to aztreonam. Use in pregnancy appears to be safe. It is in the monobactam family of medications. Aztreonam inhibits cell wall synthesis by blocking peptidoglycan crosslinking to cause bacterial death.

Aztreonam was approved for medical use in the United States in 1986. It was removed from the World Health Organization's List of Essential Medicines in 2019. It is available as a generic medication. It is a manufactured version of a chemical from the bacterium Chromobacterium violaceum.

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