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.)
Tigemonam
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 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.
They have no cross-hypersensitivity reactions with penicillin but like penicillins can trigger seizures in patients with history of seizures.
References
^Klaus R. Lindner, Daniel P. Bonner, William H. Koster. "Monobactams". Kirk‐Othmer Encyclopedia of Chemical Technology. Wiley-VCH. doi:10.1002/0471238961.1315141512091404.a01.CS1 maint: Uses authors parameter (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. Metal Ions in Life Sciences. 19. Berlin: de Gruyter GmbH. pp. 181–202. doi:10.1515/9783110527872-013. ISBN 978-3-11-052691-2.
^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.
External links
Monobactams at the US National Library of Medicine Medical Subject Headings (MeSH)
v
t
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Antibiotics active on the cell wall and envelope (J01C-J01D)
Intracellular
Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
5. β-ラクタム系抗生物質:作用機序、耐性および有害作用 beta lactam antibiotics mechanisms of action and resistance and adverse effects
English Journal
Expanded Substrate Activity of OXA-24/40 in Carbapenem-Resistant Acinetobacter baumannii Involves Enhanced Binding Loop Flexibility.
Staude MW1, Leonard DA2, Peng JW1.
Biochemistry.Biochemistry.2016 Nov 29;55(47):6535-6544. Epub 2016 Nov 11.
Gram-negative bacteria resist β-lactam antibiotics primarily by deploying β-lactamase proteins that hydrolytically destroy the antibiotics. In clinical settings, these bacteria are producing variant β-lactamases with "gain-of-activity" mutations that inactivate a broader range of β-lactams. Lear
Deciphering the Resistome of the Widespread Pseudomonas aeruginosa Sequence Type 175 International High-Risk Clone through Whole-Genome Sequencing.
Cabot G1, López-Causapé C1, Ocampo-Sosa AA2, Sommer LM3, Domínguez MÁ4, Zamorano L1, Juan C1, Tubau F4, Rodríguez C2, Moyà B1, Peña C5, Martínez-Martínez L2,6, Plesiat P7, Oliver A8.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2016 Nov 21;60(12):7415-7423. Print 2016 Dec.
Whole-genome sequencing (WGS) was used for the characterization of the frequently extensively drug resistant (XDR) Pseudomonas aeruginosa sequence type 175 (ST175) high-risk clone. A total of 18 ST175 isolates recovered from 8 different Spanish hospitals were analyzed; 4 isolates from 4 different Fr
Return to sender: the need to re-address patient antibiotic allergy labels in Australia and New Zealand.
Trubiano JA1,2,3, Worth LJ4,5, Urbancic K6,7, Brown TM8, Paterson DL8; Australasian Society for Infectious Diseases Clinical Research Network, Lucas M9; Australasian Society of Clinical Immunology and Allergy, Phillips E10,11.
Internal medicine journal.Intern Med J.2016 Nov;46(11):1311-1317. doi: 10.1111/imj.13221.
BACKGROUND/AIM: Antibiotic allergies are frequently reported and have significant impacts upon appropriate prescribing and clinical outcomes. We surveyed infectious diseases physicians, allergists, clinical immunologists and hospital pharmacists to evaluate antibiotic allergy knowledge and service d
… The product 11 was transformed to an intermediate for the synthesis of monobactam antibiotic carmonam. … Chemoselective epimerization of cis-β-lactam 13 was accomplished with trifluoroacetic acid, and the resulting trans-isomer 14 was converted into an intermediate of monobactam antibiotic aztreonam. …
Synthesis of Novel Monobactams Bearing an (R)-1-Hydroxyethyl Group and an (S)-1-Carbamoyl-oxyethyl Group at the C_<3,4>-Positions
小尾 紀行,伊藤 芳雄,寺島 孜郎
Chemical & pharmaceutical bulletin 38(4), 917-924, 1990-04-25
Various structural types of monobactams bearing an (R)-1-hydroxyethyl and an (S)-1-carbamoyloxyethyl group at the C_<3,4>-positions, respectively, could be synthesized from (3S, 4S)-4-[(S)-1-ben …
mon·o·bac·tam (mon'ō-bak'tam), A class of antibiotic that has a monocyclic β-lactam nucleus and is structurally different from other β-lactams; for example, aztreonam. monobactam /mon·o·bac·tam/ (-bak´tam) 1. a class of synthetic ...
The only commercially available monobactam antibiotic is aztreonam. Other examples of monobactams are tigemonam, [1] nocardicin A, and tabtoxin. References ^ Fuchs PC, Jones RN, Barry AL (March 1988). "In vitro. Agents ...