cefuroxime

Also known as Anaptivan, 640/359, Kefuros, Ceftin, Ximos, Zinacef, Zinacef danmark, Cefuroxim

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. It is used by mouth or by injection into a vein or muscle.

Chemical data

Formula: C16H16N4O8S
Molecular weight: 424.4 g/mol
IUPAC name: (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
InChIKey: JFPVXVDWJQMJEE-IZRZKJBUSA-N
XLogP: -0.2
Polar surface area: 199 Å²
H-bond donors: 3
H-bond acceptors: 10
Formal charge: 0

via PubChem

Research

6,163 papers

Cefuroxime axetil.Drug intelligence & clinical pharmacy · 1988
Cefuroxime axetil.The Journal of antimicrobial chemotherapy · 1988
Cefuroxime: antimicrobial activity, Pharmacology, and clinical efficacy.Therapeutic drug monitoring · 1983
Cefuroxime axetil in the treatment of sinusitis. A review.Archives of family medicine · 1994
Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy.Drugs · 1996

via PubMed

Wikidata facts

Mass: 424.069

Show 5 more facts

Commons category: Cefuroxime
chemical formula: C₁₆H₁₆N₄O₈S
isomeric SMILES: CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
canonical SMILES: CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
World Health Organisation international non-proprietary name: cefuroxime

Sources (4)

via Wikidata · CC0

~6 min read

Article

5 sections

Contents

Medical uses
Side effects
Related compounds
Trade names
References

{{Drugbox | Watchedfields = changed | verifiedrevid = 460025245 | IUPAC_name = (6R,7R)-3-{[(Aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | image = Cefuroxime enantiomers skeletal formula labelled.svg | width = 400 | image_class = skin-invert-image | alt = Skeletal formula of cefuroxime | image2 = Cefuroxime_enantiomers_ball-and-stick_models_from_xtal_2000.png | image_class2 = bg-transparent | width2 = 400 | alt2 = Ball-and-stick models of cefuroxime based on X-ray crystallography data.