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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2012))
IUPAC Name Click here for help
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 Ceftaroline, Ceftaroline fosamil
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
Search Google for chemical match using the InChIKey ZCCUWMICIWSJIX-NQJJCJBVSA-N
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UniChem Compound Search for chemical match using the InChIKey ZCCUWMICIWSJIX-NQJJCJBVSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZCCUWMICIWSJIX-NQJJCJBVSA-N