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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created using several sources including: http://www.thelancet.com/journals/laneur/article/PIIS1474-4422(14)70148-6/abstract

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

Curator's Comment: SYN115 enters the brain and exerts dose-dependent regional effects. SYN115 crosses the blood-brain barrier and alters neuronal firing.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.74 μg/mL
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOZADENANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
35.1 μg × h/mL
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOZADENANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOZADENANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

60, 120, 180, or 240 mg twice daily for 12 weeks
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:15:25 UTC 2023
Edited
by admin
on Fri Dec 15 18:15:25 UTC 2023
Record UNII
D9K857J81I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOZADENANT
INN   USAN  
USAN   INN  
Official Name English
A2A (3)
Code English
A-2A (3)
Code English
RO4494351-000
Code English
RO-4494351-002
Code English
A2A-(3)
Code English
4-HYDROXY-N-(4-METHOXY-7-MORPHOLINOBENZO(D)THIAZOL-2-YL)-4-METHYLPIPERIDINE-1-CARBOXAMIDE
Systematic Name English
SYN-115
Code English
RO-4494351000
Code English
SYN115
Code English
RO4494351
Code English
TOZADENANT [USAN]
Common Name English
RO4494351-002
Code English
Tozadenant [WHO-DD]
Common Name English
RO-4494351
Code English
RO-4494351-000
Code English
tozadenant [INN]
Common Name English
1-PIPERIDINECARBOXAMIDE, 4-HYDROXY-N-(4-METHOXY-7-(4-MORPHOLINYL)-2-BENZOTHIAZOLYL)-4-METHYL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C38149
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
Code System Code Type Description
FDA UNII
D9K857J81I
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
CAS
870070-55-6
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
EVMPD
SUB130095
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
NCI_THESAURUS
C152704
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105747
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
PUBCHEM
11618368
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
INN
9514
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
SMS_ID
100000156017
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
DRUG BANK
DB12203
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
USAN
YY-27
Created by admin on Fri Dec 15 18:15:25 UTC 2023 , Edited by admin on Fri Dec 15 18:15:25 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
selective antagonsist
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TARGET->WEAK INHIBITOR
TARGET->WEAK INHIBITOR
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ACTIVE MOIETY