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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

emapunil is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Costa B, Da Pozzo E, Martini C. (2012)
Translocator protein as a promising target for novel anxiolytics.
Curr Top Med Chem, 12 (4): 270-85. [PMID:22204481]
2. Nothdurfter C, Rammes G, Baghai TC, Schüle C, Schumacher M, Papadopoulos V, Rupprecht R. (2012)
Translocator protein (18 kDa) as a target for novel anxiolytics with a favourable side-effect profile.
J Neuroendocrinol, 24 (1): 82-92. [PMID:21609361]
3. Owen DR, Lewis AJ, Reynolds R, Rupprecht R, Eser D, Wilkins MR, Bennacef I, Nutt DJ, Parker CA. (2011)
Variation in binding affinity of the novel anxiolytic XBD173 for the 18 kDa translocator protein in human brain.
Synapse, 65 (3): 257-9. [PMID:21132812]
4. Owen DR, Phillips A, O'Connor D, Grey G, Aimola L, Nicholas R, Matthews PM. (2022)
Human pharmacokinetics of XBD173 and etifoxine distinguish their potential for pharmacodynamic effects mediated by translocator protein.
Br J Clin Pharmacol, 88 (9): 4230-4236. [PMID:35524344]
5. Rupprecht R, Rammes G, Eser D, Baghai TC, Schüle C, Nothdurfter C, Troxler T, Gentsch C, Kalkman HO, Chaperon F et al.. (2009)
Translocator protein (18 kD) as target for anxiolytics without benzodiazepine-like side effects.
Science, 325 (5939): 490-3. [PMID:19541954]
6. Yanamoto K, Kumata K, Yamasaki T, Odawara C, Kawamura K, Yui J, Hatori A, Suzuki K, Zhang MR. (2009)
[18F]FEAC and [18F]FEDAC: Two novel positron emission tomography ligands for peripheral-type benzodiazepine receptor in the brain.
Bioorg Med Chem Lett, 19 (6): 1707-10. [PMID:19217778]