Ceftizoxime

Title: Ceftizoxime
CAS Registry Number: 68401-81-0
CAS Name: (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
Additional Names: (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)
Molecular Formula: C13H13N5O5S2
Molecular Weight: 383.40
Percent Composition: C 40.72%, H 3.42%, N 18.27%, O 20.87%, S 16.73%
Literature References: Injectable third generation cephalosporin antibiotic related to cefotaxime, q.v. Exhibits broad spectrum activity and resistance to b-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).
Properties: Crystals, mp 227° (dec).
Melting point: mp 227° (dec)
Derivative Type: Sodium salt
CAS Registry Number: 68401-82-1
Manufacturers' Codes: FK-749; FR-13479; SKF-88373
Trademarks: Cefizox (Fujisawa); Ceftix (Boehringer, Mann.); Ceftizon (Bago); Epocelin (Fujisawa); Eposerin (Farmitalia)
Molecular Formula: C13H12N5NaO5S2
Molecular Weight: 405.38
Percent Composition: 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).
Toxicity data: LD50 in mice, rats (mg/kg): ~6000 i.v. (Fukuhara)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
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Ceftizoxime
Ceftizoxime.png
Systematic (IUPAC) name
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names Cefizox
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a684043
Legal status  ?
Identifiers
CAS number 68401-81-0 68401-82-1
ATC code J01DD07
PubChem CID 6533629
ChemSpider 5018818
UNII C43C467DPE YesY
KEGG D07658
ChEMBL CHEMBL528
Chemical data
Formula C13H13N5O5S2 
Mol. mass 383.405 g/mol

Ceftizoxime is a third-generation cephalosporin available for parenteral administration. Unlike other 3rd generation cephalosporins, in ceftizoxime the whole C-3 side chain has been removed to prevent deactivation by hydrolytic enzymes. It rather resembles cefotaxime in its properties, but is not subjected to metabolism.