1951. Ceftizoxime

Nomenclature

CAS number: 68401-81-0
(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-imino-4-thiazolyl)glyoxylamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime).
C13H13N5O5S2; mol wt 383.40.
C 40.72%, H 3.42%, N 18.27%, O 20.87%, S 16.73%.

Description and references

Injectable third generation cephalosporin antibiotic related to cefotaxime, q.v. Exhibits broad spectrum activity and resistance to β-lactamase hydrolysis. Prepn: T. Takaya et al., DE 2810922; eidem, US 4427674 (1978, 1984 both to Fujisawa). In vitro and in vivo antibacterial activity: T. Kamimura et al., Antimicrob. Agents Chemother. 16, 540 (1979). Comparison with other cephalosporins: M. Nishida et al., J. Antibiot. 32, 1319 (1979). Pharmacokinetics: T. Murakawa et al., Antimicrob. Agents Chemother. 17, 157 (1980). Series of articles on metabolism, pharmacology, laboratory evaluation: Arzneim.-Forsch. 30, 1662-1687 (1980). Toxicity and reproduction studies: K. Fukuhara et al., ibid. 1669. Phase I clinical study: N. Nakashima et al., J. Clin. Pharmacol. 21, 388 (1981). Reviews: J. Antimicrob. Chemother. 10, Suppl. C, 1-355 (1982); D. M. Richards, R. C. Heel, Drugs 29, 281-329 (1985).

Chemical structure

Properties

Crystals, mp 227° (dec).

Derivative

Sodium salt.

Nomenclature

CAS number: 68401-82-1
FK-749; FR-13479; SKF-88373; Cefizox (Fujisawa); Ceftix (Boehringer, Mann.); Ceftizon (Bago); Epocelin (Fujisawa); Eposerin (Farmitalia).
C13H12N5NaO5S2; mol wt 405.38.
C 38.52%, H 2.98%, N 17.28%, Na 5.67%, O 19.73%, S 15.82%.

Properties

LD50 in mice, rats (mg/kg): ≈6000 i.v. (Fukuhara).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins