Aztreonam

Aztreonam

Clinical data
Trade names	Azactam
AHFS/Drugs.com	Monograph
Pregnancy category	B1 (Au), B (U.S.)
Routes of administration	Intravenous, intramuscular, inhalation
ATC code	J01DF01 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	100% (IM) 0.1% (Oral in Rats) Unknown (Oral in humans)
Protein binding	56%
Metabolism	hepatic (minor %)
Biological half-life	1.7 hours
Excretion	Renal
Identifiers
IUPAC name 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	78110-38-0 Y
PubChem CID	54116
DrugBank	DB00355 Y
ChemSpider	4674940 Y
UNII	G2B4VE5GH8
KEGG	D00240 Y
ChEBI	CHEBI:161680 Y
ChEMBL	CHEMBL158 Y
ECHA InfoCard	100.071.652
Chemical and physical data
Formula	C13H17N5O8S2
Molar mass	435.433 g/mol
3D model (Jmol)	Interactive image
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 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

Aztreonam (trade names Azactam injection, Cayston inhalation) is a monobactam antibiotic used primarily to treat infections caused by gram-negative bacteria. It is a synthetic drug based on a simpler monobactam isolated from Chromobacterium violaceum. It is resistant to some beta-lactamases, but is inactivated by extended-spectrum beta-lactamases.

It was approved by the U.S. Food and Drug Administration (FDA) in 1986.

Nebulized forms of aztreonam are used to treat infections that are complications of cystic fibrosis and are approved for such use in Europe and the US; they and is used off-label for non-CF bronchiectasis, ventilator-associated pneumonia, chronic obstructive pulmonary disease, mycobacterial disease, and to treat infections in people who have received lung transplants.

Aztreonam has strong activity against susceptible Gram-negative bacteria, including Pseudomonas aeruginosa. It has no useful activity against Gram-positive bacteria or anaerobes. It is known to be effective against a wide range of bacteria including Citrobacter, Enterobacter, E. coli, Haemophilus, Klebsiella, Proteus, and Serratia species. The following represents MIC susceptibility data for a few medically significant microorganisms.

Synergism between aztreonam and arbekacin or tobramycin against P. aeruginosa has been suggested.