tozadenant   Click here for help

GtoPdb Ligand ID: 5611

Synonyms: SYN-115 | SYN115
PDB Ligand
Compound class: Synthetic organic
Comment: An investigational orally available and selective adenosine A2A receptor antagonist.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 115.4
Molecular weight 406.17
XLogP 1.06
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 COc1ccc(c2c1nc(s2)NC(=O)N1CCC(CC1)(C)O)N1CCOCC1
Isomeric SMILES COc1ccc(c2c1nc(s2)NC(=O)N1CCC(CC1)(C)O)N1CCOCC1
InChI InChI=1S/C19H26N4O4S/c1-19(25)5-7-23(8-6-19)18(24)21-17-20-15-14(26-2)4-3-13(16(15)28-17)22-9-11-27-12-10-22/h3-4,25H,5-12H2,1-2H3,(H,20,21,24)
InChI Key XNBRWUQWSKXMPW-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Tozadenant (SYN115) is being evaluated in Phase 3 clinical trials for the treatment of Parkinson's disease (see NCT01283594 and NCT02453386). Phase 2b results are published in [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The rationale for the development of tozadenant as an anti-Parkinson's drug is based on evidence that suggests that A2A receptors play an important role in regulating motor function. Antagonising the effect of endogenous adenosine at A2A receptors potentiates the effect of dopamine at D2 receptors and inhibits glutamate acivation of mGluR5 receptors. It is predicted that this mechanism of action will restore motor function in Parkinson's patients without causing disruptive dyskinesias.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01283594 Safety and Efficacy Study of SYN115 in Parkinson's Patients Using Levodopa to Treat End of Dose Wearing Off Phase 2/Phase 3 Interventional Biotie Therapies Inc.
NCT02453386 Safety and Efficacy Study of Tozadenant to Treat End of Dose Wearing Off in Parkinson's Patients Phase 3 Interventional Biotie Therapies Inc.