Ceftizoxime

Chemical compound

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Pharmaceutical compound

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 Edit this at Wikidata
ECHA InfoCard	100.210.846 Edit this at Wikidata
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

[edit ]

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

[edit ]

^ 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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Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) ^# Benzathine benzylpenicillin ^# Procaine benzylpenicillin ^# Phenoxymethylpenicillin (V) ^# Propicillin ^‡ Pheneticillin ^‡ Azidocillin ^‡ Clometocillin ^‡ Penamecillin ^‡
β-lactamase resistant (2nd generation)	Cloxacillin ^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin ^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin ^# Ampicillin ^# (Pivampicillin Hetacillin ^‡ Bacampicillin ^‡ Lenampicillin Metampicillin ^‡ Talampicillin ^‡) Epicillin ^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin ^‡ / Carindacillin ^‡ Temocillin ^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin ^‡ Mezlocillin ^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin ^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin ^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone ^‡ Cefazaflur ^‡ Cefradine ^‡ Cefroxadine ^‡ Ceftezole ^‡ Cefaloglycin ^‡ Cefacetrile ^‡ Cefalonium ^‡ Cefaloridine ^‡ Cefalotin Cefatrizine ^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole ^‡ Cefonicid ^‡ Ceforanide ^‡ Cefuzonam ^‡ Cephamycin (Cefoxitin Cefotetan Cefminox ^‡ Cefbuperazone ^‡ Cefmetazole ^‡) Carbacephem (Loracarbef ^‡)
3rd generation	Cefixime ^# Ceftriaxone ^# Cefotaxime ^# Antipseudomonal (Ceftazidime ^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam ^‡ Cefetamet ^‡ Cefodizime ^‡ Cefpimizole ^‡ Cefsulodin ^‡ Cefteram ^‡ Ceftiolene ^‡ Oxacephem (Flomoxef Latamoxef ^‡)
4th generation	Cefepime Cefozopran ^‡ Cefpirome Cefquinome ^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol ^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin ^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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