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
1. Charmot D, Jacobs JW, Leadbetter MR, Navre M, Carreras C, Bell N. (2013)
Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders.
Patent number: US8541448 B2. Assignee: Ardelyx, Inc.. Priority date: 31/12/2008. Publication date: 24/09/2013.
2. Spencer AG, Labonte ED, Rosenbaum DP, Plato CF, Carreras CW, Leadbetter MR, Kozuka K, Kohler J, Koo-McCoy S, He L et al.. (2014)
Intestinal inhibition of the Na+/H+ exchanger 3 prevents cardiorenal damage in rats and inhibits Na+ uptake in humans.
Sci Transl Med, 6 (227): 227ra36. [PMID:24622516]
3. Thomas RH, Luthin DR. (2015)
Current and emerging treatments for irritable bowel syndrome with constipation and chronic idiopathic constipation: focus on prosecretory agents.
Pharmacotherapy, 35 (6): 613-30. [PMID:26016701]
4. Zielińska M, Wasilewski A, Fichna J. (2015)
Tenapanor hydrochloride for the treatment of constipation-predominant irritable bowel syndrome.
Expert Opin Investig Drugs, 24 (8): 1093-9. [PMID:26065434]