Azlocillin

Azlocillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CA09 (WHO) ;
Identifiers
	IUPAC name (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	37091-66-0 ;
PubChem CID	6479523;
DrugBank	DB01061 ;
ChemSpider	4980416 ;
UNII	HUM6H389W0;
KEGG	D02339 ;
ChEBI	CHEBI:2956 ;
ChEMBL	ChEMBL1537 ;
CompTox Dashboard (EPA)	DTXSID1022639 ;
ECHA InfoCard	100.048.483
Chemical and physical data
Formula	C20H23N5O6S
Molar mass	461.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N ;
	(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. Azlocillin has been identified as a potential candidate against Lyme disease.[1]

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.[2]

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

Synthesis

Azlocillin synthesis: FR 2100682 eidem U.S. Patent 3,933,795 [3]

Azlocillin synthesis 2:[3][4]

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.

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References

https://scopeblog.stanford.edu/2020/03/30/lyme-disease-bacteria-eradicated-by-new-drug-in-early-tests/
"Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.
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.
Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID 4291383.

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[1] ttps://scopeblog.stanford.edu/2020/03/30/lyme-disease-bacteria-eradicated-by-new-drug-in-early-tests/

[2] "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.

[Konig-3] 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.

[4] Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID 4291383.

Azlocillin

Spectrum of bacterial susceptibility

Synthesis

See also

References