Chemistry:Azlocillin
Azlocillin is an acyl ampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa, and, in contrast to most cephalosporins, exhibits activity against enterococci.
Spectrum of bacterial susceptibility
Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.[1]
- Escherichia coli 1 μg/mL – 32 μg/mL
- Haemophilus spp. 0.03 μg/mL – 2 μg/mL
- Pseudomonas aeruginosa 4 μg/mL – 6.25 μg/mL
- Borrelia burgdorferi 0.5 μg/mL [2]
Synthesis
An interesting alternative synthesis of azlocillin involves activation of the substituted phenylglycine analogue 1 with 1,3-dimethyl-2-chloro-1-imidazolinium chloride (2) and then condensation with 6-APA.
Research
In March 2020, a preclinical study conducted by researchers at Stanford University and published in Scientific Reports identified azlocillin as a potential treatment candidate for Lyme disease. In a mouse model, the study demonstrated that azlocillin was effective in eradicating Borrelia burgdorferi, the bacterium responsible for the disease. Notably, azlocillin showed in vitro and in vivo efficacy against drug-tolerant "persister" cells, which can survive standard antibiotic regimens like doxycycline and ceftriaxone. The research also indicated that azlocillin was effective at lower minimum inhibitory concentrations (MIC) than conventional treatments, suggesting a potential for reduced collateral impact on the host microbiome.[2]
See also
References
- ↑ "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data". The Antimicrobial Index. toku-e.com. http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf.
- ↑ 2.0 2.1 "Azlocillin can be the potential drug candidate against drug-tolerant Borrelia burgdorferi sensu stricto JLB31". Scientific Reports (Nature Publishing Group) 10 (1). March 2020. doi:10.1038/s41598-020-59600-4. PMID 32123189. Bibcode: 2020NatSR..10.3798P.
- ↑ "Priority claimed from De2025415a" FR patent 2100682, published 1972-03-24, issued 1975-01-17, assigned to Bayer AG [De]and Bayer AG
- ↑ Disselnkotter H, Metzger KG, Hans M, Karl G, "Ureidoacetamido-penicillins", US patent 3933795, published 1976-01-20, issued 1976-01-20, assigned to Konig Hans Bodoand Konig
- ↑ 5.0 5.1 "Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften" (in German). Eur. J. Med. Chem. - Chim. Ther. 17 (1): 59–63. 1982.
- ↑ "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry 9 (6): 980–981. November 1966. doi:10.1021/jm00324a056. PMID 4291383.
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