Ceftaroline fosamil
(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
Molecular Identity
Ceftaroline fosamil
(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
PubChem CID: 9852981
Ceftaroline fosamil is a cephalosporin having [4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl and {(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl}amino side groups located at positions 3 and 7 respectively. The N-phospho prodrug of ceftaroline, a broad-spectrum antibiotic active against methicillin-resistant Staphylococcus aureus (MRSA). It is used for the treatment of adults with acute bacterial skin and skin structure infections. It has a role as an antimicrobial agent, an antibacterial drug and a prodrug. It is a cephalosporin, an iminium betaine, an oxime O-ether, an organic phosphoramidate, a member of thiadiazoles and a member of 1,3-thiazoles. It is functionally related to a ceftaroline.
2D Structure
Properties
C22H21N8O8PS4
Molecular Formula
684.70
Molecular Weight
g/mol
684.0103
Exact Mass
Da
2.3
XLogP
Drug-like (Lipinski: < 5)
330
TPSA
May have limited oral absorption
4
H-Bond Donors
17
H-Bond Acceptors
1210
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Ceftaroline fosamil229016-73-3ceftarolina fosamiloceftarolinum fosamilumCHEBI:70718(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-carboxylateCeftaroline fosamil anhydrous7P6FQA5D21DTXSID60177444Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-1-oxo-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)ethyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner saltPyridinium, 4-[2-[[(6R,7R)-2-carboxy-7-[[(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]thio]-4-thiazolyl]-1-methyl-, inner salt(6R,7R)-7-({(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl}amino)-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(6R,7R)-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-3-((4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl)sulfanyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate(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-carboxylatePyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner salt
Data from PubChem (NCBI)
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