916. Azlocillin

Nomenclature

CAS number: 37091-66-0
(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; d-α-[(imidazolidin-2-on-1-yl)carbonylamino]benzylpenicillin; Baye 6905.
C20H23N5O6S; mol wt 461.49.
C 52.05%, H 5.02%, N 15.18%, O 20.80%, S 6.95%.

Description and 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).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 37091-65-9
Azlin (Bayer); Securopen (Bayer).
C20H22N5NaO6S; mol wt 483.47.
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.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins