Monobactam

Monobactams are monocyclic and bacterially-produced β-lactam antibiotics. The β-lactam ring is not fused to another ring, in contrast to most other β-lactams.[1] Monobactams are effective only against aerobic Gram-negative bacteria (e.g., Neisseria, Pseudomonas). Siderophore-conjugated monobactams show promise for the treatment of multi drug-resistant pathogens.[2]

Aztreonam. (The four-membered ring at the bottom is the β-lactam. There is a second thiazole ring, but it is not fused to the β-lactam ring.)

Aztreonam is a commercially available monobactam antibiotic. Other examples of monobactams are tigemonam,[3] nocardicin A, and tabtoxin.

Adverse effects to monobactams can include skin rash and occasional abnormal liver functions.

Monobactam antibiotics exhibit no IgE cross-reactivity reactions with penicillin but have shown some cross reactivity with cephalosporins, most notably ceftazidime, which contains an identical side chain as aztreonam.[4] Monobactams can trigger seizures in patients with history of seizures, although the risk is lower than with penicillins.

References

  1. Klaus R. Lindner; Daniel P. Bonner; William H. Koster (2000). "Monobactams". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley-VCH. doi:10.1002/0471238961.1315141512091404.a01. ISBN 0471238961.
  2. Gumienna-Kontecka, Elzbieta; Carver, Peggy L. (2019). "Chapter 7. Building a Trojan Horse: Siderophore-Drug Conjugates for the Treatment of Infectious Diseases". In Sigel, Astrid; Freisinger, Eva; Sigel, Roland K. O.; Carver, Peggy L. (Guest editor) (eds.). Essential Metals in Medicine:Therapeutic Use and Toxicity of Metal Ions in the Clinic. Metal Ions in Life Sciences. 19. Berlin: de Gruyter GmbH. pp. 181–202. doi:10.1515/9783110527872-013. ISBN 978-3-11-052691-2. PMID 30855108.
  3. Fuchs PC, Jones RN, Barry AL (March 1988). "In vitro antimicrobial activity of tigemonam, a new orally administered monobactam". Antimicrob. Agents Chemother. 32 (3): 346–9. doi:10.1128/aac.32.3.346. PMC 172173. PMID 3259122.
  4. Alldredge, Brian K.; Corelli, Robin L.; Ernst, Michael E. (February 2012). Applied therapeutics : the clinical use of drugs. Alldredge, Brian K.,, Revision of: Koda-Kimble, Mary Anne., Revision of: Young, Lloyd Y. (Tenth ed.). Philadelphia. ISBN 9781609137137. OCLC 759179443.
  • Monobactams at the US National Library of Medicine Medical Subject Headings (MeSH)


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