Chemistry:Monobactam
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]
Aztreonam is the archetypal monobactam.[6] Other monobactams include tigemonam,[7] nocardicin A, carumonam 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.[8]
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.[9] 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.[10]
References
- ↑ 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.
- ↑ 2.0 2.1 2.2 Murray, Patrick R.; Rosenthal, Ken S.; Pfaller, Michael A. (2021). Medical microbiology (9th ed.). Elsevier. pp. 172. ISBN 978-0-323-67450-8.
- ↑ 3.0 3.1 3.2 3.3 Sherris Medical Microbiology - 7th Edition. pp. 437.
- ↑ 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.
- ↑ 5.0 5.1 5.2 5.3 "Dictionnaire médical de l'Académie de Médecine". https://www.academie-medecine.fr/le-dictionnaire/index.php?q=monobactame.
- ↑ "Monobactams - Infectious Diseases" (in en). https://www.msdmanuals.com/professional/infectious-diseases/bacteria-and-antibacterial-drugs/monobactams.
- ↑ "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.
- ↑ "Ezetimibe Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/ezetimibe.html.
- ↑ 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.
- ↑ 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
- Monobactams at the US National Library of Medicine Medical Subject Headings (MeSH)
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