CHEBI:70718 - ceftaroline fosamil

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ChEBI Name ceftaroline fosamil
ChEBI ID CHEBI:70718
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H21N8O8PS4
Net Charge 0
Average Mass 684.68500
Monoisotopic Mass 684.010
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
InChIKey ZCCUWMICIWSJIX-NQJJCJBVSA-N
SMILES [H][C@]12SCC(Sc3nc(cs3)-c3cc[n+](C)cc3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OCC)\c1nsc(NP(O)(O)=O)n1)C([O-])=O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ceftaroline fosamil (CHEBI:70718) has functional parent ceftaroline (CHEBI:70729)
ceftaroline fosamil (CHEBI:70718) has role antibacterial drug (CHEBI:36047)
ceftaroline fosamil (CHEBI:70718) has role antimicrobial agent (CHEBI:33281)
ceftaroline fosamil (CHEBI:70718) has role prodrug (CHEBI:50266)
ceftaroline fosamil (CHEBI:70718) is a 1,3-thiazoles (CHEBI:38418)
ceftaroline fosamil (CHEBI:70718) is a cephalosporin (CHEBI:23066)
ceftaroline fosamil (CHEBI:70718) is a iminium betaine (CHEBI:35285)
ceftaroline fosamil (CHEBI:70718) is a organic phosphoramidate (CHEBI:37773)
ceftaroline fosamil (CHEBI:70718) is a oxime O-ether (CHEBI:36816)
ceftaroline fosamil (CHEBI:70718) is a thiadiazoles (CHEBI:38099)
Incoming ceftaroline fosamil acetate (CHEBI:70715) has part ceftaroline fosamil (CHEBI:70718)
IUPAC Name
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}-3,4-didehydrocepham-4-carboxylate
INNs Sources
ceftarolina fosamilo WHO MedNet
ceftaroline fosamil WHO MedNet
ceftaroline fosamil WHO MedNet
ceftarolinum fosamilum WHO MedNet
Synonym Source
(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 IUPAC
Manual Xrefs Databases
4169 DrugCentral
Ceftaroline_fosamil Wikipedia
MX2012003411 Patent
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Registry Numbers Types Sources
229016-73-3 CAS Registry Number ChemIDplus
9535806 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
12 March 2018