emapunil   Click here for help

GtoPdb Ligand ID: 8704

Synonyms: AC-5216 | XBD-173 | XBD173
Compound class: Synthetic organic
Comment: Emapunil (XBD173) is an orally bioavailable translocator protein (TSPO) phenylpurine ligand. TSPO was originally identified as a molecular target for the development of new anxiolytic drugs [1-2,5]. More recently, TSPO is being pursued as a novel neuroimmunodulatory target for disease-modifying benefit in secondary progressive MS (SPMS), based on preclinical evidence of immunomodulatory effects on monocytes/macrophages and microglia that appear to induce a reparative phenotype in these immune cell types [3-4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 73.02
Molecular weight 401.19
XLogP 2.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCN(C(=O)Cn1c2nc(ncc2n(c1=O)C)c1ccccc1)Cc1ccccc1
Isomeric SMILES CCN(C(=O)Cn1c2nc(ncc2n(c1=O)C)c1ccccc1)Cc1ccccc1
InChI InChI=1S/C23H23N5O2/c1-3-27(15-17-10-6-4-7-11-17)20(29)16-28-22-19(26(2)23(28)30)14-24-21(25-22)18-12-8-5-9-13-18/h4-14H,3,15-16H2,1-2H3
InChI Key NBMBIEOUVBHEBM-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-ethyl-2-(7-methyl-8-oxo-2-phenylpurin-9-yl)-N-(phenylmethyl)acetamide
International Nonproprietary Names Click here for help
INN number INN
8432 emapunil
Synonyms Click here for help
AC-5216 | XBD-173 | XBD173
Database Links Click here for help
BindingDB Ligand 50266889
CAS Registry No. 226954-04-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL513922
DrugBank Ligand DB12666
GtoPdb PubChem SID 252166904
PubChem CID 6433109
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Wikipedia Emapunil

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Tocris
AC 5216 (links to external site)
Cat. No. 5281