VIPADENANT

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 Search

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

Description
Sources: http://www.vernalis.com/nce-pipeline/oncology/v2006 | http://www.businesswire.com/news/home/20160714006263/en/Juno-Therapeutics-Adds-Adenosine-Receptor-Antagonist-Acquisition

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23838432 \| http://www.vernalis.com/nce-pipeline/oncology/v2006	Antagonist 2778		1.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20375654	Primary		Phase II 1132	Unknown Approved Use Unknown
Cancer 592 Sources: http://adisinsight.springer.com/drugs/800016777 http://www.vernalis.com/nce-pipeline/oncology/v2006 https://www.ncbi.nlm.nih.gov/pubmed/28174424	Primary		Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/20375654	healthy n = 2 Health Status: healthy Sex: M Food Status: UNKNOWN Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/20375654	Sources: https://pubmed.ncbi.nlm.nih.gov/20375654

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003AC9	https://www.1pchem.com/search?query=1P003AC9
A2B Chem	AB52569	http://a2bchem.com/prod/AB52569
Ambeed	A155723	http://www.ambeed.com/search/Search.html?keyword=A155723
AstaTech	40693	http://astatechinc.com/CPSResult.php?CRNO=40693
BLD Pharm	BD630709	http://www.bldpharm.com/search/Search.html?keyword=BD630709
BOC Sciences	442908-10-3	http://www.bocsci.com/description.asp?cas=442908-10-3
Cayman Chemical	20239	http://www.caymanchem.com/app/template/Product.vm/catalog/20239
Chem Scene	CS-4079	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4079
ChemShuttle	169509	https://www.chemshuttle.com/catalogsearch/result/?q=169509
Excenen	EX-A1029	http://www.excenen.com/searchresultlist.php?id=EX-A1029
KeyOrganics	AS-35055	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35055
Lab Network	LN01342083	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342083
MedChem Express	HY-10857	https://www.medchemexpress.com/search.html?q=HY-10857&ft=&fa=&fp=
MolPort	MolPort-042-676-291	https://www.molport.com/shop/molecule-link/MolPort-042-676-291
Molnova	M14510	https://www.molnova.com/en/serch-list.html?keywords=M14510
MuseChem	I003568	https://www.musechem.com/product/I003568.html
ShangHai Biochempartner	BCP15984	http://www.biochempartner.com/search_BCP15984
TargetMol	T2373	https://www.targetmol.com/search?keyword=T2373
Toronto Research Chemicals	V670808	https://www.trc-canada.com/product-detail/?CatNum=V670808
eMolecules	53745180	https://orderbb.emolecules.com/search/#?query=53745180
mcule	MCULE-6859714424	https://mcule.com/MCULE-6859714424/

PubMed

Title	Date	PubMed
Antagonists of the human A(2A) adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo[4,5-d]pyrimidines.	2009 Jan 8	19072055
Novel investigational adenosine A2A receptor antagonists for Parkinson's disease.	2009 Nov	19888872
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	20375654

Patents

Sample Use Guides

In Vivo Use Guide

Healthy volunteers: daily oral vipadenant (2.5-100 mg/d for 10 or 11 days)

Route of Administration: Oral

In Vitro Use Guide

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 UTC 2023` Edited by `admin` on `Sat Dec 16 17:49:27 UTC 2023`
Record UNII	LDR3USH1NJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VIPADENANT

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