Structure via PubChem · Public domain (PubChem)
ceftobiprole
Sign in to saveCeftobiprole, sold under the brand name Zevtera among others, is a fifth-generation cephalosporin antibacterial used for the treatment of hospital-acquired pneumonia (excluding ventilator-associated pneumonia) and community-acquired pneumonia. It is marketed by Basilea Pharmaceutica under the brand names Zevtera and Mabelio. Like other cephalosporins, ceftobiprole exerts its antibacterial activity by binding to important penicillin-binding proteins and inhibiting their transpeptidase activity which is essential for the synthesis of bacterial cell walls. Ceftobiprole has high affinity for penic
In the Vinony graph
Vinony's link graph records 196 inbound references to ceftobiprole, and connects out to cephalosporin antibiotic, ceftolozane/tazobactam and antibiotic.
It is catalogued under topics including Cephalosporin antibiotics, Chemical articles with multiple CAS registry numbers and Chemical articles with multiple PubChem CIDs.
Vinony links it to 15 Wikipedia language editions.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460024985
- Drug.image
- Ceftobiprole2DCSD.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.tradename
- Zevtera, Mabelio
- Drug.DailyMedID
- Ceftobiprole
- Drug.routes_of_administration
- Intravenous
- Drug.class
- Cephalosporin antibacterial
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- DI01
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.index2_label
- as medocaril
via Wikipedia infobox
Chemical data
- Formula
- C20H22N8O6S2
- Molecular weight
- 534.6 g/mol
- IUPAC name
- (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- C1CNC[C@@H]1N2CC/C(=C\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\O)/C5=NSC(=N5)N)SC3)C(=O)O)/C2=O
- InChIKey
- VOAZJEPQLGBXGO-SDAWRPRTSA-N
- XLogP
- -2.4
- Polar surface area
- 257 Ų
- H-bond donors
- 5
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- pneumonia
via ChEMBL · EBI
Research
503 papers- Ceftobiprole.2006
- Ceftobiprole for Treatment of Complicated Staphylococcus aureus Bacteremia.The New England journal of medicine · 2023
- Ceftobiprole medocaril.Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia · 2022
- Ceftobiprole medocaril for the treatment of pneumonia.Expert review of anti-infective therapy · 2023
- Ceftobiprole Medocaril Sodium.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 2024
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 534.110372424
Show 5 more facts
- chemical formula
- C₂₀H₂₂N₈O₆S₂
- canonical SMILES
- C1CNCC1N2CCC(=CC3=C(N4C(C(C4=O)NC(=O)C(=NO)C5=NSC(=N5)N)SC3)C(=O)O)C2=O
- subject has role
- antibiotic
- isomeric SMILES
- C1CNC[C@@H]1N2CC/C(=C\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\O)/C5=NSC(=N5)N)SC3)C(=O)O)/C2=O
- Commons category
- Ceftobiprole
Sources (2)
via Wikidata · CC0
~10 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Microbiology
- Pharmacology
- History
- Society and culture
- Legal status
- References
- External links
Ceftobiprole, sold under the brand name Zevtera among others, is a fifth-generation cephalosporin antibacterial used for the treatment of hospital-acquired pneumonia (excluding ventilator-associated pneumonia) and community-acquired pneumonia. It is marketed by Basilea Pharmaceutica under the brand names Zevtera and Mabelio. Like other cephalosporins, ceftobiprole exerts its antibacterial activity by binding to important penicillin-binding proteins and inhibiting their transpeptidase activity which is essential for the synthesis of bacterial cell walls. Ceftobiprole has high affinity for penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus strains and retains its activity against strains that express divergent mecA gene homologues (mecC or mecALGA251). Ceftobiprole also binds to penicillin-binding protein 2b in Streptococcus pneumoniae (penicillin-intermediate), to penicillin-binding protein 2x in Streptococcus pneumoniae (penicillin-resistant), and to penicillin-binding protein 5 in Enterococcus faecalis.
For adults with Staphylococcus aureus bloodstream infections (bacteremia), the most common side effects include anemia, nausea, low levels of potassium in the blood (hypokalemia), vomiting, diarrhea, increased levels of certain liver tests (hepatic enzymes and bilirubin), increased blood creatinine, high blood pressure, low white blood cell count (leukopenia), fever, abdominal pain, fungal infection, headache and shortness of breath (dyspnea). For adults with acute bacterial skin and skin structure infections, the most common side effects include nausea, diarrhea, headache, injection site reaction, increased levels of hepatic enzymes, rash, vomiting and altered taste (dysgeusia). For adults with community-acquired bacterial pneumonia, the most common side effects include nausea, increased levels of hepatic enzymes, vomiting, diarrhea, headache, rash, insomnia, abdominal pain, vein inflammation (phlebitis), high blood pressure and dizziness. For children with community-acquired bacterial pneumonia, the most common side effects include vomiting, headache, increased levels of hepatic enzymes, diarrhea, infusion site reaction, vein inflammation (phlebitis) and fever.
Excerpted from Wikipedia’s “ceftobiprole” article, available under the CC BY-SA 4.0 licence.
Gallery (4)
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via Wikidata sitelinks · CC0