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Details

Stereochemistry ACHIRAL
Molecular Formula C19H26N4O4S
Molecular Weight 406.499
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOZADENANT

SMILES

COC1=CC=C(N2CCOCC2)C3=C1N=C(NC(=O)N4CCC(C)(O)CC4)S3

InChI

InChIKey=XNBRWUQWSKXMPW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C19H26N4O4S
Molecular Weight 406.499
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tozadenant (SYN115) is an adenosine A2A receptor antagonist initially developed for treatment of Parkinson's disease but may also have utility in other CNS disorders. A2a receptors are expressed in high concentration in the striatum of the brain and play an important role in regulating motor function. Tozadenant blocks the effect of endogenous adenosine at the A2a receptors, resulting in the potentiation of the effect of dopamine at the D2 receptor and inhibition of the effect of glutamate at the mGluR5 receptor. This enables restoration of motor function in Parkinson’s disease. Tozadenant has the potential for use as mono-therapy or adjunctive therapy in combination with L-Dopa and dopamine agonists for the treatment of the motor and non-motor symptoms associated with Parkinson’s disease. may also have neuroprotective effects, which raises the possibility that it could slow the deterioration of dopamine producing cells and modify disease progression. As was reported in international, multicentre, phase 2b, randomised, double-blind, placebo-controlled, parallel-group, dose-finding clinical trial of tozadenant in levodopa-treated patients with Parkinson's disease who had motor fluctuations tozadenant at 120 or 180 mg twice daily was generally well tolerated and was effective at reducing off-time.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.74 μg/mL
240 mg single, oral
TOZADENANT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
35.1 μg × h/mL
240 mg single, oral
TOZADENANT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
240 mg single, oral
TOZADENANT plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
60, 120, 180, or 240 mg twice daily for 12 weeks
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
D9K857J81I
Record Status Validated (UNII)
Record Version