Structure via PubChem · Public domain (PubChem)
ceftizoxime
Sign in to saveAlso known as FK-749, Eposerin, CEFIZOX, 7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Syn-7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acid, Cefizox, Ceftix, Ceftizoxima
Ceftizoxime is a third-generation cephalosporin available for parenteral administration. 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.
Chemical data
- Formula
- C13H13N5O5S2
- Molecular weight
- 383.4 g/mol
- 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
- SMILES
- CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
- InChIKey
- NNULBSISHYWZJU-LLKWHZGFSA-N
- XLogP
- 0
- Polar surface area
- 201 Ų
- H-bond donors
- 3
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1983
- Admin. routes
- parenteral
- Indications
- osteomyelitis, bacterial disease
via ChEMBL · EBI
Research
1,687 papers- Ceftizoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use.Drugs · 1985
- Ceftizoxime: a beta-lactamase-stable, broad-spectrum cephalosporin. Pharmacokinetics, adverse effects and clinical use.Pharmacotherapy · 1984
- Ceftizoxime and ceftazidime.Lancet (London, England) · 1984
- Ceftizoxime: a third-generation cephalosporin active against anaerobic bacteria. Committee on Antimicrobial Agents, Canadian Infectious Disease Society.CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne · 1990
- [Ceftizoxime: a new aminothiazolyl-syn-methoxy-iminocephalosporin].Medicina · 1990
via PubMed
Wikidata facts
- Subclass of
- cephalosporin antibiotic
- Mass
- 383.035811
- Has use
- medication
Show 8 more facts
- medical condition treated
- staphylococcal infection
- chemical formula
- C₁₃H₁₃N₅O₅S₂
- isomeric SMILES
- CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
- canonical SMILES
- CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)O
- World Health Organisation international non-proprietary name
- ceftizoxime
- defined daily dose
- 4
- subject has role
- bactericide
- Commons category
- Ceftizoxime
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
{{Drugbox | 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 | image = ceftizoxime.png | image_class = skin-invert-image
| tradename = Cefizox | Drugs.com = | MedlinePlus = a684043 | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “ceftizoxime” article, available under the CC BY-SA 4.0 licence.