senicapoc   Click here for help

GtoPdb Ligand ID: 2331

Synonyms: ICA-17043 | ICA17043
Compound class: Synthetic organic
Comment: Senicapoc has activity as a KCa3.1 channel inhibitor. [18]F-labelled senicapoc derivatives have been used as positron emission tomography tracers to visualise KCa3.1 channels in vivo [1,4]. A BODIPY-conjugated (fluorescent) senicapoc probe that occupies space in the channel pore is also reported [6].
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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

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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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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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 43.09
Molecular weight 323.11
XLogP 4.87
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 Fc1ccc(cc1)C(c1ccc(cc1)F)(c1ccccc1)C(=O)N
Isomeric SMILES Fc1ccc(cc1)C(c1ccc(cc1)F)(c1ccccc1)C(=O)N
InChI InChI=1S/C20H15F2NO/c21-17-10-6-15(7-11-17)20(19(23)24,14-4-2-1-3-5-14)16-8-12-18(22)13-9-16/h1-13H,(H2,23,24)
InChI Key SCTZUZTYRMOMKT-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. Brömmel K, Konken CP, Börgel F, Obeng-Darko H, Schelhaas S, Bulk E, Budde T, Schwab A, Schäfers M, Wünsch B. (2021)
Synthesis and biological evaluation of PET tracers designed for imaging of calcium activated potassium channel 3.1 (KCa3.1) channels in vivo.
RSC Adv, 11 (48): 30295-30304. [PMID:35480282]
2. Granfeldt A, Andersen LW, Vallentin MF, Hilberg O, Hasselstrøm JB, Sørensen LK, Mogensen S, Christensen S, Grejs AM, Rasmussen BS et al.. (2022)
Senicapoc treatment in COVID-19 patients with severe respiratory insufficiency-A randomized, open-label, phase II trial.
Acta Anaesthesiol Scand, 66 (7): 838-846. [PMID:35403225]
3. Jin LW, Lucente JD, Nguyen HM, Singh V, Singh L, Chavez M, Bushong T, Wulff H, Maezawa I. (2019)
Repurposing the KCa3.1 inhibitor senicapoc for Alzheimer's disease.
Ann Clin Transl Neurol, 6 (4): 723-738. [PMID:31019997]
4. Konken CP, Heßling K, Thale I, Schelhaas S, Dabel J, Maskri S, Bulk E, Budde T, Koch O, Schwab A et al.. (2022)
Imaging of the calcium activated potassium channel 3.1 (KCa 3.1) in vivo using a senicapoc-derived positron emission tomography tracer.
Arch Pharm (Weinheim), 355 (12): e2200388. [PMID:36161669]
5. Stocker JW, De Franceschi L, McNaughton-Smith GA, Corrocher R, Beuzard Y, Brugnara C. (2003)
ICA-17043, a novel Gardos channel blocker, prevents sickled red blood cell dehydration in vitro and in vivo in SAD mice.
Blood, 101 (6): 2412-8. [PMID:12433690]
6. Thale I, Maskri S, Grey L, Todesca LM, Budde T, Maisuls I, Strassert CA, Koch O, Schwab A, Wünsch B. (2023)
Imaging of KCa 3.1 Channels in Tumor Cells with PET and Small-Molecule Fluorescent Probes.
ChemMedChem, 18 (2): e202200551. [PMID:36315933]