Ceftaroline fosamil

Ceftaroline fosamil (INN) /sɛfˈtæroʊliːn/, brand name Teflaro in the US and Zinforo in Europe, is a cephalosporin antibiotic with anti-MRSA activity. Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

Ceftaroline fosamil
Clinical data
Trade namesTeflaro, Zinforo
Other namesPPI 0903, TAK-599
AHFS/Drugs.comMonograph
MedlinePlusa611014
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Protein binding20%
Elimination half-life2.5 hours
ExcretionUrine (88%), faeces (6%)
Identifiers
  • (6R,7R)-7-[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H21N8O8PS4
Molar mass684.67 g·mol−1
3D model (JSmol)
  • O=C4N3/C(=C(/Sc2nc(c1cc[n+](cc1)C)cs2)CS[C@@H]3[C@@H]4NC(=O)C(=N\OCC)/c5nc(sn5)NP(=O)(O)O)C([O-])=O
  • InChI=1S/C22H21N8O8PS4/c1-3-38-26-13(16-25-21(43-28-16)27-39(35,36)37)17(31)24-14-18(32)30-15(20(33)34)12(9-40-19(14)30)42-22-23-11(8-41-22)10-4-6-29(2)7-5-10/h4-8,14,19H,3,9H2,1-2H3,(H4-,24,25,27,28,31,33,34,35,36,37)/b26-13-/t14-,19-/m1/s1 N
  • Key:ZCCUWMICIWSJIX-NQJJCJBVSA-N N
 NY (what is this?)  (verify)

Ceftaroline is being developed by Forest Laboratories, under a license from Takeda. Ceftaroline received approval from the U.S. Food and Drug Administration (FDA) for the treatment of community-acquired bacterial pneumonia and acute bacterial skin infections on 29 October 2010. In vitro studies show it has a similar spectrum to ceftobiprole, the only other fifth-generation cephalosporin to date, although no head-to-head clinical trials have been conducted. Ceftaroline and ceftobiprole are on an unnamed subclass of cephalosporins by the Clinical and Laboratory Standards Institute (CLSI).

It was removed from the World Health Organization's List of Essential Medicines in 2019.

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