Ceftizoxime

Ceftizoxime
Clinical data
Trade names	Cefizox
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a684043
ATC code	J01DD07 (WHO) ;
Identifiers
	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;
CAS Number	68401-81-0 68401-82-1;
PubChem CID	6533629;
ChemSpider	5018818;
UNII	C43C467DPE;
KEGG	D07658;
ChEMBL	ChEMBL528;
CompTox Dashboard (EPA)	DTXSID5022772 ;
ECHA InfoCard	100.210.846
Chemical and physical data
Formula	C13H13N5O5S2
Molar mass	383.40 g·mol−1

Ceftizoxime is a third-generation cephalosporin available for parenteral administration.^[1] Unlike other third-generation cephalosporins, the whole C-3 side chain in ceftizoxime has been removed to prevent deactivation by hydrolytic enzymes. It rather resembles cefotaxime in its properties, but is not subject to metabolism. It was removed from the US Market in 2007.

Synthesis

Injectable third generation cephalosporin antibiotic related to cefotaxime, q.v. Exhibits broad spectrum activity and resistance to β-lactamase hydrolysis.

Ceftizoxime synthesis:^[2]^[3]

References

^ Aldridge KE (1990). "An update on the in vitro activity of ceftizoxime and other cephalosporin/cephamycin antimicrobial agents against clinically significant anaerobic bacteria". Clinical Therapeutics. 12 Suppl C: 3–12. PMID 2202509.
^ DE 2810922, Takaya T, Hisashi T, Kiyoshi T, Toshiyuki C, "New cepham compounds and processes for the production thereof", issued 29 August 1985, assigned to Fujisawa
^ US 4427674, Takaya T, Hisashi T, Kiyoshi T, Toshiyuki C, "Cephem compounds", issued 24 January 1984, assigned to Fujisawa

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[Aldridge_1990-1] Aldridge KE (1990). "An update on the in vitro activity of ceftizoxime and other cephalosporin/cephamycin antimicrobial agents against clinically significant anaerobic bacteria". Clinical Therapeutics. 12 Suppl C: 3–12. PMID 2202509.

[2] DE 2810922, Takaya T, Hisashi T, Kiyoshi T, Toshiyuki C, "New cepham compounds and processes for the production thereof", issued 29 August 1985, assigned to Fujisawa

[3] US 4427674, Takaya T, Hisashi T, Kiyoshi T, Toshiyuki C, "Cephem compounds", issued 24 January 1984, assigned to Fujisawa

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