sutezolid   Click here for help

GtoPdb Ligand ID: 12772

Synonyms: MMV688756 | PF-02341272 | PNU-100480 | U-100480
PDB Ligand
Compound class: Synthetic organic
Comment: Originally developed by Upjohn (later incorporated into Pfizer), sutezolid is an oxazolidinone class antibacterial with potent antimycobacterial activity [1]. It is being clinically evaluated as a treatment for tuberculosis (TB).
Sutezolid is included in the Medicines for Malaria (MMV) and Drugs for Neglected Diseases Initiative (DNDi) Pandemic Response Box.
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 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 87.18
Molecular weight 353.41
XLogP 1.57
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 CC(=O)NC[C@H]1CN(C2=CC=C(C(=C2)F)N3CCSCC3)C(=O)O1
Isomeric SMILES CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCSCC3)F
InChI InChI=1S/C16H20FN3O3S/c1-11(21)18-9-13-10-20(16(22)23-13)12-2-3-15(14(17)8-12)19-4-6-24-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
InChI Key FNDDDNOJWPQCBZ-ZDUSSCGKSA-N
No information available.
Summary of Clinical Use Click here for help
Sutezolid has completed Phase 2 trials in patients with drug-sensitive pulmonary tuberculosis (TB) as a monotherapy (NCT01225640)[4] and in combination with bedaquiline, moxifloxacin, and delamanid (NCT03959566). It will also be evaluated as a TB treatment, in combination with bedaquiline and pretomanid, in a Phase 2/3 trial (NCT05686356) that started recruitment in 2023.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The antibacterial MMOA of oxazolidinones is inhibition of protein synthesis by blocking function of the bacterial 50S ribosomal subunit [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05686356 A Pan-TB Regimen Targeting Host and Microbe Phase 2/Phase 3 Interventional The Aurum Institute NPC
NCT03959566 PanACEA Sutezolid Dose-finding and Combination Evaluation Phase 2 Interventional Ludwig-Maximilians - University of Munich
NCT01225640 PNU-100480 In Newly Diagnosed, Drug Sensitive Patients With Pulmonary TB; Early Bactericidal Activity; Whole Blood Assay Phase 2 Interventional Sequella, Inc. This first trial of sutezolid in patients with pulmonary tuberculosis found the drug to be generally safe, well tolerated, and with detectable bactericidal activity in sputum and blood. 4