vipadenant   Click here for help

GtoPdb Ligand ID: 5612

Synonyms: BIIB 014 | BIIB014 | V2006
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vipadenant is an adenosine A2 receptor antagonist that can promote T cell activation. It was originally investigated as a potential therapeutic for Parkinson's disease but development for this indication was discontinued at Phase 2 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 121.67
Molecular weight 321.13
XLogP 1.2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Nc1nc(c2ccco2)c2c(n1)n(nn2)Cc1ccc(c(c1)C)N
Isomeric SMILES Nc1nc(c2ccco2)c2c(n1)n(nn2)Cc1ccc(c(c1)C)N
InChI 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)
InChI Key HQSBCDPYXDGTCL-UHFFFAOYSA-N
References
1. Gillespie RJ, Bamford SJ, Botting R, Comer M, Denny S, Gaur S, Griffin M, Jordan AM, Knight AR, Lerpiniere J et al.. (2009)
Antagonists of the human A(2A) adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo[4,5-d]pyrimidines.
J. Med. Chem., 52 (1): 33-47. [PMID:19072055]
2. Pinna A. (2014)
Adenosine A2A receptor antagonists in Parkinson's disease: progress in clinical trials from the newly approved istradefylline to drugs in early development and those already discontinued.
CNS Drugs, 28 (5): 455-74. [PMID:24687255]