posizolid   Click here for help

GtoPdb Ligand ID: 12762

Synonyms: AZD2563 | AZD5847
Compound class: Synthetic organic
Comment: Posizolid (AZD2563 or AZD5847) is an oxazolidinone class antibacterial with activity against Gram-positive bacteria [5]. It has antimycobacterial activity [2] and was being developed by AstraZeneca as a potential therapeutic for tuberculosis (TB).
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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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 CDK toolkit. 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 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 121.13
Molecular weight 465.4
XLogP -0.24
No. Lipinski's rules broken 0
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.

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Canonical SMILES C1=C(CCN(C1)C(=O)[C@H](CO)O)C2=C(C=C(C=C2F)N3C[C@H](COC4=NOC=C4)OC3=O)F
Isomeric SMILES C1CN(CC=C1C2=C(C=C(C=C2F)N3C[C@@H](OC3=O)COC4=NOC=C4)F)C(=O)[C@H](CO)O
InChI InChI=1S/C21H21F2N3O7/c22-15-7-13(26-9-14(33-21(26)30)11-31-18-3-6-32-24-18)8-16(23)19(15)12-1-4-25(5-2-12)20(29)17(28)10-27/h1,3,6-8,14,17,27-28H,2,4-5,9-11H2/t14-,17+/m1/s1
InChI Key HBUJYEUPIIJJOS-PBHICJAKSA-N
No information available.
Summary of Clinical Use Click here for help
Posizolid completed Phase 2 clinical evaluation for the treatment of TB but AstraZeneca has removed it from their development pipeline. This may be due to hematologic and hepatic side-effects and because it does not offer additional benefit over existing oxazolidinones for the treatment of TB [3].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Posizolid, like other oxazolidinones, inhibits protein synthesis by blocking function of the bacterial 50S ribosomal subunit [2,4].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01516203 Phase 2a EBA Trial of AZD5847 Phase 2 Interventional National Institute of Allergy and Infectious Diseases (NIAID) 1,3