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ceftobiprole

Structure via PubChem · Public domain (PubChem)

EntityQ5057301· pop 16· linked from 196 articles

ceftobiprole

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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 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

via PubMed

Wikidata facts

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 sections
Contents
  • 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.

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