Ceftobiprole

Ceftobiprole
Clinical data
Trade namesZevtera, Mabelio
Other namesRO0639141-000,[1] BAL9141,[2] ceftobiprole medocaril
AHFS/Drugs.comZevtera
License data
Routes of
administration		Intravenous
Drug classCephalosporin antibacterial
ATC code
Legal status
Legal status
Identifiers
  • (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)- 2-nitroso-1-oxoethyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)- 3-pyrrolidinyl]-3-pyrrolidinylidene]methyl]-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.129.666 Edit this at Wikidata
Chemical and physical data
FormulaC20H22N8O6S2
Molar mass534.57 g·mol−1
3D model (JSmol)
  • C1CNC[C@@H]1N2CC/C(=C\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\O)/c5nc(sn5)N)SC3)C(=O)O)/C2=O
  • InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1 ☒N
  • Key:VOAZJEPQLGBXGO-SDAWRPRTSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Ceftobiprole, sold under the brand name Zevtera among others, is a fifth-generation[7] 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.[8][9][10][11][12][13] 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.[14]

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).[15] 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).[15] 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.[15] 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.[15]

Ceftobiprole medocaril was approved for medical use in the United States in April 2024.[15][16]

  1. ^ Hebeisen P, Heinze-Krauss I, Angehrn P, Hohl P, Page MG, Then RL (March 2001). "In vitro and in vivo properties of Ro 63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci". Antimicrobial Agents and Chemotherapy. 45 (3): 825–836. doi:10.1128/AAC.45.3.825-836.2001. PMC 90381. PMID 11181368.
  2. ^ Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ (December 2002). "In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci". The Journal of Antimicrobial Chemotherapy. 50 (6): 915–932. doi:10.1093/jac/dkf249. PMID 12461013.
  3. ^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.
  4. ^ "Zevtera Product information". Health Canada. 23 April 2010. Archived from the original on 19 February 2024. Retrieved 13 April 2024.
  5. ^ "Zevtera Product information". Health Canada. 20 March 2018. Archived from the original on 30 April 2024. Retrieved 13 April 2024.
  6. ^ "Zevtera (ceftobiprole medocaril sodium for injection), for intravenous use" (PDF). Archived (PDF) from the original on 6 April 2024. Retrieved 6 April 2024.
  7. ^ Scheeren TW (1 January 2015). "Ceftobiprole medocaril in the treatment of hospital-acquired pneumonia". Future Microbiology. 10 (12): 1913–1928. doi:10.2217/fmb.15.115. PMID 26573022.
  8. ^ "Basilea announces distribution agreement with Cardiome to commercialize antibiotic Zevtera/Mabelio (ceftobiprole) in Europe and Israel". Basilea (Press release). 12 September 2017. Archived from the original on 7 April 2024. Retrieved 7 April 2024.
  9. ^ "Basilea to launch Zevtera/Mabelio (ceftobiprole medocaril) in Europe through a commercial services provider" (Press release). Basilea Pharmaceutica. Archived from the original on 31 March 2019. Retrieved 20 September 2016.
  10. ^ "Basilea announces launch of antibiotic Zevtera (ceftobiprole medocaril) in Germany". Basilea (Press release). 5 December 2014. Archived from the original on 7 April 2024. Retrieved 7 April 2024.
  11. ^ "Swissmedic approves Basilea's antibiotic Zevtera (ceftobiprole medocaril) for the treatment of pneumonia". Basilea (Press release). 22 December 2014. Archived from the original on 7 April 2024. Retrieved 7 April 2024.
  12. ^ "Basilea signs exclusive distribution agreement for Zevtera (ceftobiprole medocaril) in the Middle East and North Africa with Hikma Pharmaceuticals LLC". Basilea (Press release). 15 October 2015. Archived from the original on 7 April 2024. Retrieved 7 April 2024.
  13. ^ "Basilea announces that Health Canada approved Zevtera for the treatment of bacterial lung infections". Basilea (Press release). 12 October 2015. Archived from the original on 7 April 2024. Retrieved 7 April 2024.
  14. ^ Syed YY (September 2014). "Ceftobiprole medocaril: a review of its use in patients with hospital- or community-acquired pneumonia". Drugs. 74 (13): 1523–1542. doi:10.1007/s40265-014-0273-x. PMID 25117196. S2CID 2925496.
  15. ^ a b c d e "FDA Approves New Antibiotic for Three Different Uses". U.S. Food and Drug Administration (FDA) (Press release). 3 April 2024. Archived from the original on 13 April 2024. Retrieved 12 April 2024. Public Domain This article incorporates text from this source, which is in the public domain.
  16. ^ "Novel Drug Approvals for 2024". U.S. Food and Drug Administration (FDA). 29 April 2024. Archived from the original on 30 April 2024. Retrieved 30 April 2024.