Azlocillin

Title: Azlocillin
CAS Registry Number: 37091-66-0
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[[(2R)-[[(2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: D-a-[(imidazolidin-2-on-1-yl)carbonylamino]benzylpenicillin
Manufacturers' Codes: Bay e 6905
Molecular Formula: C20H23N5O6S
Molecular Weight: 461.49
Percent Composition: C 52.05%, H 5.02%, N 15.18%, O 20.80%, S 6.95%
Literature References: Semi-synthetic, broad-spectrum acylureido penicillin. Prepn: H. Disselnkotter, K. G. Metzger, FR 2100682; eidem, US 3933795 (1971, 1976 both to Bayer); H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982). In vitro studies: D. Stewart et al., Antimicrob. Agents Chemother. 11, 865 (1977). In vitro and in vivo activity: G. K. Daikos et al., Curr. Chemother., Proc. 10th Int. Congr. Chemother., 1977 (Amer. Soc. Microbiol., Washington, D.C., 1978) 1, pp 626-8. Pharmacokinetics: P. Fiegel, K. Becker, Antimicrob. Agents Chemother. 14, 288 (1978). Comparison with other penicillins: J. M. Andrews, K. A. Bedford, ibid. 559. Clinical studies: H. Lode et al., Infection 5, 163 (1977); E. B. Helm et al., Dtsch. Med. Wochenschr. 102, 1211 (1977). Series of articles on antibacterial activity, pharmacology, and clinical trials: Arzneim.-Forsch. 29, 1915-2032 (1979); Infection 10, Suppl. 3, S121-S266 (1982); J. Antimicrob. Chemother. 11, Suppl. B, 1-239 (1983).
Derivative Type: Sodium salt
CAS Registry Number: 37091-65-9
Trademarks: Azlin (Bayer); Securopen (Bayer)
Molecular Formula: C20H22N5NaO6S
Molecular Weight: 483.47
Percent Composition: C 49.69%, H 4.59%, N 14.49%, Na 4.76%, O 19.86%, S 6.63%
Properties: Pale yellow crystals, sol in water, methanol, DMF. Slightly sol in ethanol, isopropanol.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
Azolitmin Azomycin Azosemide Azoxybenzene Azoxystrobin

Azlocillin
Azlocillin skeletal.svg
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
Legal status  ?
Identifiers
CAS number 37091-66-0 YesY
ATC code J01CA09
PubChem CID 6479523
DrugBank DB01061
ChemSpider 4980416 YesY
UNII HUM6H389W0 YesY
KEGG D02339 YesY
ChEBI CHEBI:2956 YesY
ChEMBL CHEMBL1537 YesY
Chemical data
Formula C20H23N5O6S 
Mol. mass 461.491 g/mol
 YesY (what is this?)  (verify)

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.