ceftaroline fosamil   Click here for help

GtoPdb Ligand ID: 10899

Synonyms: PPI-0903 | TAK-599 | Teflaro® | Zinforo®
Approved drug
ceftaroline fosamil is an approved drug (FDA (2010), EMA (2012))
Compound class: Synthetic organic
Comment: Ceftaroline fosamil is a fifth-generation cephalosporin prodrug which is hydrolysed to the active form, ceftaroline, in vivo. It has anti-MRSA activity [1]. Ceftaroline was removed from the World Health Organization's List of Essential Medicines in 2019.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 340.13
Molecular weight 684.01
XLogP 0.78
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCO/N=C(/c1nsc(n1)NP(=O)(O)O)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])Sc1scc(n1)c1cc[n+](cc1)C
Isomeric SMILES CCO/N=C(/c1nsc(n1)NP(=O)(O)O)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])Sc1scc(n1)c1cc[n+](cc1)C
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
InChI Key ZCCUWMICIWSJIX-NQJJCJBVSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2012))
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
8827 ceftaroline fosamil
Synonyms Click here for help
PPI-0903 | TAK-599 | Teflaro® | Zinforo®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1444, 1419
Other databases
CAS Registry No. 229016-73-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL501122
DrugBank Ligand DB06590
DrugCentral Ligand 4169
GtoPdb PubChem SID 405560340
PubChem CID 9852981
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