Chemistry:Monobactam

From HandWiki
Short description: Monocyclic β-lactam antibiotics
Aztreonam
Drug class
Aztreonam structure.svg
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.)
Class identifiers
UseBacterial infection
ATC codeJ01DF
External links
MeSHD008997

Monobactams are bacterially-produced monocyclic β-lactam antibiotics. The β-lactam ring is not fused to another ring, in contrast to most other β-lactams.[1]

Monobactams are narrow-spectrum antibiotics effective only against aerobic Gram-negative[2] bacilli.[3][4] Due to their narrow spectrum, monobactams can be used to treat infections by susceptible bacteria without disrupting the patient's microbiota. Monobactams are nevertheless seldom used.[2]

Aztreonam is the principal[3] and sole commercially available member of monobactams.[5] Other monobactams include tigemonam,[6] nocardicin A, and tabtoxin.[citation needed]

Pharmacology

Monobactams exert their antibacterial effects by binding to penicillin-binding proteins, thereby inhibiting bacterial wall synthesis. Monobactams are synergetic with aminoglycosides, andpiperacillin.[4]

Bacterial resistance to monobactams have been observed, and is mediated by bacterial betalactamases.[4]

Adverse effects

Adverse effects to monobactams can include skin rash and occasional abnormal liver functions.[citation needed]

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.[7] Monobactams can trigger seizures in patients with history of seizures, although the risk is lower than with penicillins.[citation needed]

Research

Siderophore-conjugated monobactams show promise for the treatment of multi drug-resistant pathogens.[8]

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. 2.0 2.1 Murray, Patrick R.; Rosenthal, Ken S.; Pfaller, Michael A. (2021). Medical microbiology (9th ed.). Elsevier. pp. 172. ISBN 978-0-323-67450-8. 
  3. 3.0 3.1 Ritter, James; Flower, Rod; Henderson, Graeme; Loke, Yoon Kong; MacEwan, David; Rang, H. P. (2020). Rang & Dale's Pharmacology (9th ed.). Elsevier. pp. 665. ISBN 978-0-7020-7448-6. 
  4. 4.0 4.1 4.2 "Dictionnaire médical de l'Académie de Médecine". https://www.academie-medecine.fr/le-dictionnaire/index.php?q=monobactame. 
  5. "Monobactams - Infectious Diseases" (in en). https://www.msdmanuals.com/professional/infectious-diseases/bacteria-and-antibacterial-drugs/monobactams. 
  6. "In vitro antimicrobial activity of tigemonam, a new orally administered monobactam". Antimicrob. Agents Chemother. 32 (3): 346–9. March 1988. doi:10.1128/aac.32.3.346. PMID 3259122. 
  7. 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. 
  8. 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. et al.. Essential Metals in Medicine:Therapeutic Use and Toxicity of Metal Ions in the Clinic. 19. Berlin: de Gruyter GmbH. 181–202. doi:10.1515/9783110527872-013. ISBN 978-3-11-052691-2. 

External links