Ceftobiprole

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Ceftobiprole
Ceftobiprole2DCSD.svg
Systematic (IUPAC) name
(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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
Routes of
administration		 Intravenous
Identifiers
CAS Number 209467-52-7 N
Template:CAS (medocaril)
ATC code J01DI01 (WHO) [1]
PubChem CID: 6918430
ChemSpider 21106277 YesY
UNII 5T97333YZK YesY
KEGG D08885 YesY
ChEMBL CHEMBL520642 N
Chemical data
Formula C20H22N8O6S2
Molecular mass 534.568 g/mol
  • O=C3N1/C(=C(\CS[C@@H]1[C@@H]3NC(=O)C(\N=O)=C2/NSC(\N)=N2)/C=C4\CCN(C4=O)[C@@H]5CCNC5)C(O)=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/h5,10,12,18,22,26H,1-4,6-7H2,(H2,21,24)(H,23,29)(H,32,33)/b8-5+,14-11+/t10-,12-,18-/m1/s1 YesY
  • Key:LXLDMYXULSBRCX-KOGKARRDSA-N YesY
 NYesY (what is this?)  (verify)

Ceftobiprole (Zeftera/Zevtera) is a fifth-generation[2] cephalosporin antibiotic with activity against methicillin-resistant Staphylococcus aureus, penicillin-resistant Streptococcus pneumoniae, Pseudomonas aeruginosa, and enterococci.[3][4][5] It was discovered by Basilea Pharmaceutica[6] and was developed by Johnson & Johnson Pharmaceutical Research and Development.[7] It has been shown to be statistically noninferior to the combination of vancomycin and ceftazidime for the treatment of skin and soft tissue infections.[8]

It has been described as a fifth-generation cephalosporin,[9][10] though acceptance for this terminology is not universal.

Pharmacology

Like other cephalosporins, ceftobiprole inhibits bacterial growth by blocking penicillin-binding protein, a key enzyme involved in cell wall synthesis. Ceftobiprole inhibits the 2a penicillin-binding protein (PBP) of methicillin-resistant Staphylococcus aureus and the 2x PBP of Streptococcus pneumoniae,[4] as well as the classic PBP-2 of MSSA. Ceftobiprole is resistant to staphylococcal β-lactamase.[6]

Mode of administration

Ceftobiprole is given intravenously; it cannot be given by mouth.

Regulatory approvals

Ceftobiprole has been approved for use in Canada, Switzerland, and the European Union.[11] It is under review by regulatory authorities in the United States, Australia, Russia, and South Africa.[12] In November 2008, the US FDA declined to approve ceftobiprole, citing data integrity concerns with two of the supporting studies,[13] and prompting Basilea to sue Johnson & Johnson for breach of license agreement on February 2009.[14]

Synonyms

  • RO0639141-000[6]
  • BAL9141[15]
  • Ceftobiprole medocaril

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 6.2 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Basilea.com
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Basilea antibiotic to treat pneumonia wins European backing. Reuters, ZURICH | Wed Oct 23, 2013.
  12. ↑ Basilea superbug drug approved in Canada, Reuters News, June 30, 2008
  13. ↑ http://www.dancewithshadows.com/pillscribe/ceftobiprole-antibiotic-to-fight-tougher-bacterial-infections-fails-to-win-approval-in-us/
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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