Ceftaroline fosamil

Ceftaroline fosamil

Clinical data
Trade names	Teflaro, Zinforo
License data	EU EMA: Zinforo US FDA: Ceftaroline
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Routes of administration	Intravenous
ATC code	J01DI02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	20%
Biological half-life	2.5 hours
Excretion	Urine (88%), faeces (6%)
Identifiers
IUPAC name (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
Synonyms	PPI 0903, TAK-599
CAS Number	400827-46-5 Y
PubChem CID	16007393 9852981
ChemSpider	8028692 N
UNII	EZ9W6O5S09
ChEBI	CHEBI:70718 N
ChEMBL	CHEMBL501122 N
ECHA InfoCard	100.210.879
Chemical and physical data
Formula	C24H25N8O10PS4
Molar mass	744.736661 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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?)

Ceftaroline fosamil (INN) /sɛfˈtæroʊliːn/, brand name Teflaro in the US and Zinforo in Europe, is an advanced-generationcephalosporin antibiotic. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and Gram-positive bacteria. It retains the activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

Ceftaroline is being developed by Forest Laboratories, under a license from Takeda. Ceftaroline has received approval from the U.S. Food and Drug Administration for the treatment of community-acquired bacterial pneumonia and acute bacterial skin infections on October 29, 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).

Ceftaroline is a novel cephalosporin with activity against MRSA with phase III clinical trials for complicated skin and skin structure infections with reported non-inferior efficacy against MRSA compared to vancomycin and aztreonam. In 2009, ceftaroline had completed phase-III clinical trials for community-acquired pneumonia comparing it against ceftriaxone with non-inferior results and similar adverse reaction profile. However, only results for phase-II clinical trials in treatment of complicated skin and skin structure infections have been published. Sept 2009 : Phase III trials results reported. On September 8, 2010, the FDA Advisory Committee recommended approval for the treatment of community acquired bacterial pneumonia and complicated skin and skin structure infections. In Oct 2010, the FDA approval was gained for community-acquired bacterial pneumonia and acute bacterial skin and skin structure infections, including MRSA.