Monobactam

Aztreonam
Drug class
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
Legal status
In Wikidata
Tigemonam

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[2] effective only against (strictly or facultatively[3]) aerobic Gram-negative bacilli,[4][5][3] exhibiting a high level of resistance to beta-lactamases of these organisms.[3] Due to their narrow spectrum, monobactams can be used to treat infections by susceptible bacteria without disrupting the patient's microbiota.[2] Monobactams are nevertheless seldom used.[2]

[6] Other monobactams include tigemonam,[7] nocardicin A, and tabtoxin. An example of a monobactam that lacks antibiotic activity, but is used clinically for other purposes, is the cholesterol absorption inhibitor ezetimibe which is used to treat hypercholesterolemia[citation needed]

Pharmacology

Monobactams exert their antibacterial effects by binding to penicillin-binding proteins (PBPs), thereby inhibiting bacterial wall synthesis.[5] Monobactams exhibit poor affinity for PBPs of Gram-positive bacteria as well as of strictly anaerobic bacteria, resulting in a lack of significant antimicrobial activity against these kinds of organisms.[3] Monobactams are synergetic with aminoglycosides, and piperacillin.[5]

Bacterial resistance to monobactams have been observed, and is mediated by bacterial beta-lactamases.[5]

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.[8] 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.[9]

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. ^ a b c Murray, Patrick R.; Rosenthal, Ken S.; Pfaller, Michael A. (2021). Medical microbiology (9th ed.). Elsevier. p. 172. ISBN 978-0-323-67450-8.
  3. ^ a b c d Sherris Medical Microbiology - 7th Edition. p. 437.
  4. ^ Ritter, James; Flower, Rod; Henderson, Graeme; Loke, Yoon Kong; MacEwan, David; Rang, H. P. (2020). Rang & Dale's Pharmacology (9th ed.). Elsevier. p. 665. ISBN 978-0-7020-7448-6.
  5. ^ a b c d "Dictionnaire médical de l'Académie de Médecine". www.academie-medecine.fr. Retrieved 2024-01-13.
  6. ^ "Monobactams - Infectious Diseases". MSD Manual Professional Edition. Retrieved 2024-01-13.
  7. ^ 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.
  8. ^ 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.{{cite book}}: CS1 maint: location missing publisher (link)
  9. ^ 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. Vol. 19. Berlin: de Gruyter GmbH. pp. 181–202. doi:10.1515/9783110527872-013. ISBN 978-3-11-052691-2. PMID 30855108. S2CID 73727689. {{cite book}}: |editor4-first= has generic name (help); |journal= ignored (help)

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