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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2D Structure
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Physico-chemical Properties
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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
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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
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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).
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].