Azlocillin

Azlocillin
Clinical data
Trade namesSecuropen
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[((2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.483 Edit this at Wikidata
Chemical and physical data
FormulaC20H23N5O6S
Molar mass461.49 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)NCC2)[C@H]4SC3(C)C
  • InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1 checkY
  • Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N checkY
  (verify)

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.

Synthesis

Azlocillin synthesis: eidem
Azlocillin synthesis 2:

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.

See also

References

  1. ↑ "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.
  2. 1 2 Pothineni VR, Potula HS, Ambati A, Mallajosyula VV, Sridharan B, Inayathullah M, et al. (March 2020). "Azlocillin can be the potential drug candidate against drug-tolerant Borrelia burgdorferi sensu stricto JLB31". Scientific Reports. 10 (1) 3798. Nature Publishing Group. Bibcode:2020NatSR..10.3798P. doi:10.1038/s41598-020-59600-4. PMC 7052277. PMID 32123189.
  3. ↑ FR 2100682, "Priority claimed from De2025415a", published 1972-03-24, issued 1975-01-17, assigned to Bayer AG [De] and Bayer AG
  4. ↑ US patent 3933795, Disselnkotter H, Metzger KG, Hans M, Karl G, "Ureidoacetamido-penicillins", published 1976-01-20, issued 1976-01-20, assigned to Konig Hans Bodo and Konig
  5. 1 2 Koenig HB, Metzer KG, Offe HA, Schroeck W (1982). "Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften". Eur. J. Med. Chem. - Chim. Ther. (in German). 17 (1): 59–63.
  6. ↑ Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–981. doi:10.1021/jm00324a056. PMID 4291383.