tenapanor   Click here for help

GtoPdb Ligand ID: 8449

Synonyms: AZD-1722 | AZD1722 | Ibsrela® | RDX-5791
Approved drug
tenapanor is an approved drug (FDA (2019))
Compound class: Synthetic organic
Comment: Tenapanor is an inhibitor of the sodium/hydrogen exchanger 3 (NHE3, gene symbol SLC9A3) [4]. Tenapanor is Compound 236 in patent US8541448 [1].
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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
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 CDK toolkit. 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 18
Hydrogen bond donors 6
Rotatable bonds 33
Topological polar surface area 234.76
Molecular weight 1142.31
XLogP 4.43
No. Lipinski's rules broken 3
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.

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Canonical SMILES O=C(NCCOCCOCCNS(=O)(=O)c1cccc(c1)C1CN(C)Cc2c1cc(Cl)cc2Cl)NCCCCNC(=O)NCCOCCOCCNS(=O)(=O)c1cccc(c1)C1CN(C)Cc2c1cc(Cl)cc2Cl
Isomeric SMILES O=C(NCCOCCOCCNS(=O)(=O)c1cccc(c1)[C@@H]1CN(C)Cc2c1cc(Cl)cc2Cl)NCCCCNC(=O)NCCOCCOCCNS(=O)(=O)c1cccc(c1)[C@@H]1CN(C)Cc2c1cc(Cl)cc2Cl
InChI InChI=1S/C50H66Cl4N8O10S2/c1-61-31-43(41-27-37(51)29-47(53)45(41)33-61)35-7-5-9-39(25-35)73(65,66)59-15-19-71-23-21-69-17-13-57-49(63)55-11-3-4-12-56-50(64)58-14-18-70-22-24-72-20-16-60-74(67,68)40-10-6-8-36(26-40)44-32-62(2)34-46-42(44)28-38(52)30-48(46)54/h5-10,25-30,43-44,59-60H,3-4,11-24,31-34H2,1-2H3,(H2,55,57,63)(H2,56,58,64)/t43-,44-/m0/s1
InChI Key DNHPDWGIXIMXSA-CXNSMIOJSA-N
No information available.
Summary of Clinical Use Click here for help
Tenapanor was approved by the FDA (in September 2019) as a twice daily oral pill for the treatment of constipation-predominant irritable bowel syndrome (IBS-C). In October 2023 the FDA approval was expanded to include using tenapanor to reduce serum phosphorus patients with chronic kidney disease (CKD) on dialysis and for whom phosphate binders are inadequate or unsuitable.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tenapanor selectively inhibits sodium uptake in the intestines, causing the retention of fluid and ions in the gastrointestinal (GI) tract. This has a two-fold action, firstly reducing levels of sodium entering [2] and secondly stimulating fecal excretion. The compound is substantially impermeable to the layer of gut epithelial cells, which restricts its action to the internal surface of the GI tract. As an anti-constipation therapy, tenapanor acts as a prosecretory agent, restoring appropriate fluid secretion in the gut, and thereby improving stool consistency and intestinal transit (concomitantly decreasing intestinal discomfort) [3].
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For extended ADME data see the following:

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