1928. Cefodizime

Nomenclature

CAS number: 69739-16-8
(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72(Z)-(O-methyloxime).
C20H20N6O7S4; mol wt 584.67.
C 41.09%, H 3.45%, N 14.37%, O 19.16%, S 21.94%.

Description and references

Third generation cephalosporin antibiotic with immunomodulating activity; derivative of cefotaxime, q.v. Prepn: BE 865632; W. Dürckheimer et al., US 4278793 (1978, 1981 both to Hoechst AG); and antibacterial activity: J. Blumbach et al., J. Antibiot. 40, 29 (1987). In vitro comparative antibacterial spectrum: R. N. Jones et al., Antimicrob. Agents Chemother. 20, 760 (1981); and β-lactamase stability: M. Limbert et al., J. Antibiot. 37, 892 (1984). In vivo antibacterial activity: N. Klesel et al., ibid. 1712. Enhancement of immune response in vivo: M. Limbert et al., ibid. 1719; and ex vivo: A. Fietta et al., Chemotherapy (Basel) 34, 430 (1988). HPLC determn in biological fluids: T. Marunaka et al., J. Chromatogr. 420, 329 (1987). Pharmacokinetics: N. Klesel et al., J. Antibiot. 37, 901 (1984); in humans: E. E. Dagrosa et al., Clin. Ther. 10, 18 (1987). Clinical study in urogenital gonorrhea: A. H. van der Willigen et al., Antimicrob. Agents Chemother. 32, 426 (1988). Physical properties, toxicology and structure-activity relationships: A. Bryskier et al., J. Antimicrob. Chemother. 26, Suppl. C, 1 (1990). Series of articles on pharmacology, pharmacokinetics and clinical studies: Chemotherapy (Tokyo) 36, Suppl. 5, 1-980 (1988); and immunomodulating activity: J. Antimicrob. Chemother. 26, Suppl. C, 1-134 (1990).

Chemical structure

Properties

[α]D25 -55.9°. pK1 2.85; pK2 3.37; pK3 4.18. uv max (water): 228, 260, 288 nm (log ε 4.25, 4.25, 4.20).

Derivative

Disodium salt.

Nomenclature

CAS number: 86329-79-5
HR-221; THR-221; Kenicef (Taiho); Neucef (HMR); Timecef (HMR).
C20H18N6Na2O7S4; mol wt 628.63.
C 38.21%, H 2.89%, N 13.37%, Na 7.31%, O 17.82%, S 20.40%.

Properties

White to yellow crystalline powder. Soly (g/l): water ≈270. LD50 in mice, rabbits (mg/kg): 4000-8000 i.v. both species; in rats (mg/kg): 4000-8000 i.v., 15000-17500 s.c., 8000-11000 i.p. (Bryskier).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins