Structure via PubChem · Public domain (PubChem)
ceftazidime
Sign in to saveAlso known as (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, CAZ, ceftazidime anhydrous
Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.
Key facts
- Drug.ChEBI
- 3508
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460024696
- Drug.image
- Ceftazidime.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Ceftazidime-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Fortaz, Tazicef, others
- Drug.MedlinePlus
- a686007
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Ceftazidime
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- Intravenous, intramuscular, inhalation
- Drug.class
- Third-generation cephalosporin
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- DD02
via Wikipedia infobox
Chemical data
- Formula
- C22H22N6O7S2
- Molecular weight
- 546.6 g/mol
- IUPAC name
- 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(6R,7R)-2-carboxy-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoate
- SMILES
- CC(C)(C(=O)[O-])O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)O
- InChIKey
- ORFOPKXBNMVMKC-DWVKKRMSSA-N
- XLogP
- 0.4
- Polar surface area
- 245 Ų
- H-bond donors
- 3
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
14,624 papers- Klebsiella pneumoniae Carbapenemase Variants Resistant to Ceftazidime-Avibactam: an Evolutionary Overview.Antimicrobial agents and chemotherapy · 2022
- Ceftazidime-Avibactam: A Review in the Treatment of Serious Gram-Negative Bacterial Infections.Drugs · 2018
- Ceftazidime review.Drug intelligence & clinical pharmacy · 1985
- Ceftazidime dosing in obese patients: is it time for more?Expert opinion on drug metabolism & toxicology · 2022
- Ceftazidime for respiratory infections.Expert opinion on pharmacotherapy · 2012
via PubMed
Wikidata facts
- Mass
- 546.099139
Show 7 more facts
- chemical formula
- C₂₂H₂₂N₆O₇S₂
- isomeric SMILES
- CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
- canonical SMILES
- CC(C)(C(=O)O)ON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
- World Health Organisation international non-proprietary name
- ceftazidime
- defined daily dose
- 4
- Commons category
- Ceftazidime
- stylized name
- cefTAZidime
Sources (9)
via Wikidata · CC0
~6 min read
Article
11 sectionsContents
- Medical uses
- Spectrum of activity
- Side effects
- Contraindications
- Precautions
- Pregnancy
- Mechanism of action
- Chemistry
- See also
- References
- External links
Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.
Common side effects include nausea, allergic reactions, and pain at the site of injection. Other side effects may include Clostridioides difficile diarrhea. It is not recommended in people who have had previous anaphylaxis to a penicillin. Its use is relatively safe during pregnancy and breastfeeding. It is in the third-generation cephalosporin family of medications and works by interfering with the bacteria's cell wall.