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Details

Stereochemistry ACHIRAL
Molecular Formula C16H15N7O
Molecular Weight 321.3366
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIPADENANT

SMILES

CC1=CC(CN2N=NC3=C2N=C(N)N=C3C4=CC=CO4)=CC=C1N

InChI

InChIKey=HQSBCDPYXDGTCL-UHFFFAOYSA-N
InChI=1S/C16H15N7O/c1-9-7-10(4-5-11(9)17)8-23-15-14(21-22-23)13(19-16(18)20-15)12-3-2-6-24-12/h2-7H,8,17H2,1H3,(H2,18,19,20)

HIDE SMILES / InChI

Molecular Formula C16H15N7O
Molecular Weight 321.3366
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Vipadenant (V2006) is a small molecule, adenosine A2A receptor antagonist that was being investigated in Parkinson's disease. Due to safety concerns development ceased in 2010 and the rights were regained from Biogen Idec in 2011 with no further investment made. In October 2014, RedoxTherapies licensed Vipadenant as it has the potential to disrupt an immunosuppressive mechanism of tumour protection, generating improved efficacy for immunotherapies of certain cancers when used in combination with other drugs.

Approval Year

Targets

Targets

Conditions
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day multiple, oral
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antagonists of the human A(2A) adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo[4,5-d]pyrimidines.
2009 Jan 8
Novel investigational adenosine A2A receptor antagonists for Parkinson's disease.
2009 Nov
An open-label, positron emission tomography study to assess adenosine A2A brain receptor occupancy of vipadenant (BIIB014) at steady-state levels in healthy male volunteers.
2010 Mar-Apr
Patents

Sample Use Guides

Healthy volunteers: daily oral vipadenant (2.5-100 mg/d for 10 or 11 days)
Route of Administration: Oral
Vipadenant showed excellent binding affinity for A2A (Ki=1.3 nM) and had modest selectivity against A1 and A2B (Ki = 63 nM), while it showed good selectivity against A3 (Ki = 1005 nM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:49:27 GMT 2023
Edited
by admin
on Sat Dec 16 17:49:27 GMT 2023
Record UNII
LDR3USH1NJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VIPADENANT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
VER-A00049
Code English
VER-11135
Code English
V2006
Code English
VER-A-00049
Code English
vipadenant [INN]
Common Name English
Vipadenant [WHO-DD]
Common Name English
3-((4-AMINO-3-METHYLPHENYL)METHYL)-7-(FURAN-2-YL)-3H-(1,2,3)TRIAZOLO(4,5-D)PYRIMIDIN-5-AMINE
Systematic Name English
VER-A-00-11
Code English
BIIB014
Code English
VER-A00-11
Code English
V-2006
Code English
3H-1,2,3-TRIAZOLO(4,5-D)PYRIMIDIN-5-AMINE, 3-((4-AMINO-3-METHYLPHENYL)METHYL)-7-(2-FURANYL)-
Systematic Name English
CEB-4520
Code English
VIPADENANT [USAN]
Common Name English
BIIB-014
Code English
VER-ADO-49
Code English
Classification Tree Code System Code
NCI_THESAURUS C38149
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
NCI_THESAURUS C2139
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
Code System Code Type Description
INN
9329
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
FDA UNII
LDR3USH1NJ
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
CAS
442908-10-3
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL3545386
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL447664
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
NCI_THESAURUS
C152892
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID90196103
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
CAS
1148126-34-4
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
SUPERSEDED
SMS_ID
300000034483
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
USAN
WW-153
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
PUBCHEM
21874557
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
CAS
874193-81-4
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
SUPERSEDED
DRUG BANK
DB06625
Created by admin on Sat Dec 16 17:49:27 GMT 2023 , Edited by admin on Sat Dec 16 17:49:27 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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ACTIVE MOIETY