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.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Indicated for acute complicated bacterial skin and skin structure infections and community-acquired bacterial pneumonia, caused by susceptible microorganisms.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)