Azlocillin

Azlocillin

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	37091-66-0
ATC code	J01CA09 (WHO)
PubChem	CID 6479523
DrugBank	DB01061
ChemSpider	4980416
UNII	HUM6H389W0
KEGG	D02339
ChEBI	CHEBI:2956
ChEMBL	CHEMBL1537
Chemical data
Formula	C20H23N5O6S
Molar mass	461.491 g/mol
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
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Azlocillin is an acylampicillin 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

Synthesis

Azlocillin synthesis: FR 2100682  eidem U.S. Patent 3,933,795 ^[2]

Azlocillin synthesis 2:^[2][3]

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.

See also

• Methicillin

References

1. http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf
2. H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982).
3. Bauer, Victor J.; Safir, S. R. (1966). "Octamethylbiguanide Perchlorate". Journal of Medicinal Chemistry 9 (6): 980. doi:10.1021/jm00324a056. PMID 4291383.