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Aztreonam
Systematic (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
Identifiers
CAS number 78110-38-0
ATC code J01DF01
PubChem 54116
DrugBank APRD00815
ChemSpider 4674940
Chemical data
Formula C 13H17N5O8S2  
Mol. mass 435.433 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 100% (IM)
Protein binding 56%
Metabolism hepatic (minor %)
Half life 1.7 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat. B1 (Au), B (U.S.)
Legal status ℞-only (U.S.)
Routes Intravenous and intramuscular
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Aztreonam (trade name Azactam) is a synthetic monocyclic beta-lactam antibiotic (a monobactam), with the nucleus based on a simpler monobactam isolated from Chromobacterium violaceum. It was approved by the U.S. Food and Drug Administration (FDA) in 1986. It is resistant to some beta-lactamases, but is inactivated by extended-spectrum beta-lactamases.

Contents

Mechanism of action

Aztreonam is similar in action to penicillin. It inhibits mucopeptide synthesis in the bacterial cell wall, thereby blocking peptidoglycan crosslinking. It has a very high affinity for penicillin-binding protein 3 (PBP-3) and mild affinity for PBP-1a. Aztreonam binds the penicillin-binding proteins of gram-positive and anaerobic bacteria very poorly and is largely ineffective against them.[1] Aztreonam is bactericidal but less so than some of the cephalosporins.

Indications and spectrum of activity

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.[2]

Synergism between aztreonam and arbekacin or tobramycin against Pseudomonas aeruginosa has been suggested.[3]

Aztreonam is often used in patients who are penicillin allergic or who can not tolerate aminoglycosides

Administration

Aztreonam must be administered intravenously, as the compound is poorly absorbed when given via the oral route. Phase III trials are currently in progress to measure its delivery in inhaled form, using an ultrasonic nebulizer.

Common adverse effects

Reported side-effects include injection site reactions, rash, and rarely toxic epidermal necrolysis. Gastrointestinal side effects generally include diarrhea and nausea and vomiting. There may be drug-induced eosinophilia. There is limited cross-reactivity between aztreonam and other beta-lactam antibiotics, and it is generally considered safe to admininister aztreonam to patients with hypersensitivity (allergies) to penicillins.[1]

Aztreonam is considered Pregnancy category B.

References

  1. ^ a b AHFS DRUG INFORMATION 2006 (2006 ed ed.). American Society of Health-System Pharmacists. 2006.  
  2. ^ Mosby's Drug Consult 2006 (16 ed ed.). Mosby, Inc.. 2006.  
  3. ^ Kobayashi, Y., Uchida, H., Kawakami Y. (1992). "Synergy with aztreonam and arbekacin or tobramycin against Pseudomonas aeruginosa isolated from blood". J Antimicrob Chemother 30 (6): 871–872. PMID 1289363.  


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