1955. Cefuzonam

Nomenclature

CAS number: 82219-78-1
(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (-)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime); 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1,2,3-thiadiazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid; CL-118523.
C16H15N7O5S4; mol wt 513.59.
C 37.42%, H 2.94%, N 19.09%, O 15.58%, S 24.97%.

Description and references

Semi-synthetic third generation cephalosporin. Prepn and bactericidal activity: W. V. Curran, A. S. Ross, FR 2488258; eidem, US 4399132 (1982, 1983 both to Am. Cyanamid); eidem, J. Antibiot. 36, 179 (1983). Improved prepn of sodium salt: K. Naito et al., EP 145395 (1985 to Takeda). In vitro antibacterial spectrum: M. Hikada et al., J. Antimicrob. Chemother. 18, 585 (1986). Toxicity study: S. Takita, Chemotherapy (Tokyo) 34, Suppl. 3, 96 (1986). Conference proceedings: Recent Adv. Chemother., Antimicrobial Sect. 2., Proc. 14th Int. Congr. Chemother., Kyoto 1985, J. Ishigami, Ed. (Univ. Tokyo Press, Tokyo, 1985) pp 887-908. Series of articles: Chemotherapy (Tokyo) 34, Suppl. 3, 1-732 (1986).

Chemical structure

Properties

White amorphous solid. LD50 in female, male mice, female, male rats (mg/kg): 4117, >4800, 4281, 4222 i.v.; 6424, 6783, >8000, >8000 i.p.; all >10000 orally (Takita).

Derivative

Sodium salt dihydrate.

Nomenclature

L-105 (Lederle); CL-251931; LJC-10305; Cosmosin (Nippon Lederle).
C16H14N7NaO5S4.2H2O; mol wt 571.61.
C 33.62%, H 3.17%, N 17.15%, Na 4.02%, O 19.59%, S 22.44%.

Properties

Yellowish crystalline powder. Sol in water.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins