Monobactam: Difference between revisions
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{{Short description|Monocyclic β-lactam antibiotics}} |
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{{Infobox drug class |
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| Name = Aztreonam |
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'''Monobactams''' are [[beta-lactam|β-lactam]] compounds wherein the β-lactam ring is alone and not [[Bicyclic molecule|fused]] to another ring, in contrast to most other β-lactams. They are effective only against aerobic [[Gram-negative bacteria]] (e.g., ''Neisseria'', ''Pseudomonas''). |
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| Image = Aztreonam structure.svg |
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| ImageClass = skin-invert-image |
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| Alt = |
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| Use = Bacterial infection |
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| Biological_target = |
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| ATC_prefix = J01DF |
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| MeshID = D008997 |
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| Drugs.com = |
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| Consumer_Reports = |
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| medicinenet = |
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}} |
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Currently The only commercially available monobactam antibiotic is [[aztreonam]]. |
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'''Monobactams''' are bacterially-produced monocyclic [[β-lactam antibiotic]]s. The [[beta-lactam|β-lactam]] ring is not [[Bicyclic molecule|fused]] to another ring, in contrast to most other β-lactams.<ref>{{cite journal|title=Monobactams|author1=Klaus R. Lindner|author2=Daniel P. Bonner|author3=William H. Koster|journal=Kirk-Othmer Encyclopedia of Chemical Technology|publisher=Wiley-VCH|doi=10.1002/0471238961.1315141512091404.a01|year=2000|isbn=0471238961}}</ref> |
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Monobactams are [[Narrow-spectrum antibiotic|narrow-spectrum antibiotics]]<ref name=":0">{{Cite book |last=Murray |first=Patrick R. |title=Medical microbiology |last2=Rosenthal |first2=Ken S. |last3=Pfaller |first3=Michael A. |date=2021 |publisher=Elsevier |isbn=978-0-323-67450-8 |edition=9th |location= |pages=172}}</ref> effective only against (strictly or facultatively<ref name=":12">{{Cite book |title=Sherris Medical Microbiology - 7th Edition |pages=437}}</ref>) aerobic [[Gram-negative bacteria|Gram-negative]] [[bacilli]],<ref name=":1">{{Cite book |last=Ritter |first=James |title=Rang & Dale's Pharmacology |last2=Flower |first2=Rod |last3=Henderson |first3=Graeme |last4=Loke |first4=Yoon Kong |last5=MacEwan |first5=David |last6=Rang |first6=H. P. |date=2020 |publisher=Elsevier |isbn=978-0-7020-7448-6 |edition=9th |location= |pages=665}}</ref><ref name=":2">{{Cite web |title=Dictionnaire médical de l'Académie de Médecine |url=https://www.academie-medecine.fr/le-dictionnaire/index.php?q=monobactame |access-date=2024-01-13 |website=www.academie-medecine.fr}}</ref><ref name=":12" /> exhibiting a high level of resistance to [[Beta-lactamase|beta-lactamases]] of these organisms.<ref name=":12" /> Due to their narrow spectrum, monobactams can be used to treat infections by susceptible bacteria without disrupting the patient's [[microbiota]].<ref name=":0" /> Monobactams are nevertheless seldom used.<ref name=":0" /> |
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Other examples of monobactams are [[tigemonam]],<ref name="pmid3259122">{{cite journal |vauthors=Fuchs PC, Jones RN, Barry AL |title=In vitro antimicrobial activity of tigemonam, a new orally administered monobactam |journal=Antimicrob. Agents Chemother. |volume=32 |issue=3 |pages=346–9 |date=March 1988 |pmid=3259122 |pmc=172173 |doi= 10.1128/aac.32.3.346|url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3259122}}</ref> [[nocardicin A]], and [[tabtoxin]]. |
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<ref>{{Cite web |title=Monobactams - Infectious Diseases |url=https://www.msdmanuals.com/professional/infectious-diseases/bacteria-and-antibacterial-drugs/monobactams |access-date=2024-01-13 |website=MSD Manual Professional Edition |language=en}}</ref> Other monobactams include [[tigemonam]],<ref name="pmid3259122">{{cite journal |vauthors=Fuchs PC, Jones RN, Barry AL |date=March 1988 |title=In vitro antimicrobial activity of tigemonam, a new orally administered monobactam |journal=Antimicrob. Agents Chemother. |volume=32 |issue=3 |pages=346–9 |doi=10.1128/aac.32.3.346 |pmc=172173 |pmid=3259122}}</ref> [[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]]{{cn|date=January 2023}} |
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== Pharmacology == |
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They have no cross-hypersensitivity reactions with [[penicillin]] but like penicillins can trigger seizures in patients with history of seizures. |
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Monobactams exert their antibacterial effects by binding to [[penicillin-binding proteins|penicillin-binding proteins (PBPs)]], thereby inhibiting bacterial wall synthesis.<ref name=":2" /> 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.<ref name=":12" /> Monobactams are synergetic with [[Aminoglycoside|aminoglycosides]], and [[piperacillin]].<ref name=":2" /> |
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Bacterial resistance to monobactams have been observed, and is mediated by bacterial beta-lactamases.<ref name=":2" /> |
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== Adverse effects == |
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Monobactam antibiotics exhibit no [[IgE]] [[Cross-reactivity#In immunology|cross-reactivity reactions]] with [[penicillin]] but have shown some cross reactivity with [[cephalosporin]]s, most notably [[ceftazidime]], which contains an identical side chain as aztreonam.<ref>{{Cite book|title=Applied therapeutics : the clinical use of drugs.|others=Alldredge, Brian K.,, Revision of: Koda-Kimble, Mary Anne., Revision of: Young, Lloyd Y.|isbn=9781609137137|edition=Tenth|location=Philadelphia|oclc=759179443|last1 = Alldredge|first1 = Brian K.|last2 = Corelli|first2 = Robin L.|last3 = Ernst|first3 = Michael E.|date = February 2012}}</ref> Monobactams can trigger seizures in patients with history of seizures, although the risk is lower than with penicillins.{{cn|date=January 2023}} |
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== Research == |
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[[Siderophore]]-conjugated monobactams show promise for the treatment of multi drug-resistant pathogens.<ref>{{cite book |last1=Gumienna-Kontecka |first1=Elzbieta |title=Essential Metals in Medicine:Therapeutic Use and Toxicity of Metal Ions in the Clinic |last2=Carver |first2=Peggy L. |date=2019 |journal=Metal Ions in Life Sciences |publisher=de Gruyter GmbH |isbn=978-3-11-052691-2 |editor1-last=Sigel |editor1-first=Astrid |volume=19 |location=Berlin |pages=181–202 |chapter=Chapter 7. Building a Trojan Horse: Siderophore-Drug Conjugates for the Treatment of Infectious Diseases |doi=10.1515/9783110527872-013 |pmid=30855108 |editor2-last=Freisinger |editor2-first=Eva |editor3-last=Sigel |editor3-first=Roland K. O. |editor4-last=Carver |editor4-first=Peggy L. (Guest editor) |s2cid=73727689}}</ref> |
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==References== |
==References== |
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{{CephalosporinAntiBiotics}} |
{{CephalosporinAntiBiotics}} |
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[[Category:Monobactam antibiotics| ]] |
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Latest revision as of 02:02, 24 November 2024
| Aztreonam | |
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| Drug class | |
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| Class identifiers | |
| Use | Bacterial infection |
| ATC code | J01DF |
| External links | |
| MeSH | D008997 |
| Legal status | |
| In Wikidata | |
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
[edit]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
[edit]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
[edit]Siderophore-conjugated monobactams show promise for the treatment of multi drug-resistant pathogens.[9]
References
[edit]- ^ 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.
- ^ 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.
- ^ a b c d Sherris Medical Microbiology - 7th Edition. p. 437.
- ^ 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.
- ^ a b c d "Dictionnaire médical de l'Académie de Médecine". www.academie-medecine.fr. Retrieved 2024-01-13.
- ^ "Monobactams - Infectious Diseases". MSD Manual Professional Edition. Retrieved 2024-01-13.
- ^ 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.
- ^ 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) - ^ 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)
External links
[edit]- Monobactams at the U.S. National Library of Medicine Medical Subject Headings (MeSH)