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Chemistry

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Also known as: 1234423-95-0, Azd1722, Azd-1722, Tenapanor free base, Rdx-5791, Azd 1722

Molecular Formula

C₅₀H₆₆Cl₄N₈O₁₀S₂

Molecular Weight

1145.0 g/mol

InChI Key

DNHPDWGIXIMXSA-CXNSMIOJSA-N

FDA UNII

WYD79216A6

Tenapanor is a novel, small molecule medication approved in September 2019 for the treatment of constipation-predominant irritable bowel-syndrome (IBS-C). It was first designed and synthesized in 2012. As an inhibitor of the sodium/hydrogen exchanger isoform 3 (NHE3) transporter, it is the first and currently only medication within its class and therefore exists as a novel alternative in the treatment of IBS-C.

1 2D Structure

Tenapanor

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[2-[2-[2-[[3-[(4S)-6,8-dichloro-2-methyl-3,4-dihydro-1H-isoquinolin-4-yl]phenyl]sulfonylamino]ethoxy]ethoxy]ethyl]-3-[4-[2-[2-[2-[[3-[(4S)-6,8-dichloro-2-methyl-3,4-dihydro-1H-isoquinolin-4-yl]phenyl]sulfonylamino]ethoxy]ethoxy]ethylcarbamoylamino]butyl]urea

2.1.2 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

2.1.3 InChI Key

DNHPDWGIXIMXSA-CXNSMIOJSA-N

2.1.4 Canonical SMILES

CN1CC(C2=C(C1)C(=CC(=C2)Cl)Cl)C3=CC(=CC=C3)S(=O)(=O)NCCOCCOCCNC(=O)NCCCCNC(=O)NCCOCCOCCNS(=O)(=O)C4=CC=CC(=C4)C5CN(CC6=C5C=C(C=C6Cl)Cl)C

2.1.5 Isomeric SMILES

CN1C[C@H](C2=C(C1)C(=CC(=C2)Cl)Cl)C3=CC(=CC=C3)S(=O)(=O)NCCOCCOCCNC(=O)NCCCCNC(=O)NCCOCCOCCNS(=O)(=O)C4=CC=CC(=C4)[C@@H]5CN(CC6=C5C=C(C=C6Cl)Cl)C

2.2 Other Identifiers

2.2.1 UNII

WYD79216A6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Azd1722

2. Rdx5791

2.3.2 Depositor-Supplied Synonyms

1. 1234423-95-0

2. Azd1722

3. Azd-1722

4. Tenapanor Free Base

5. Rdx-5791

6. Azd 1722

7. Rdx 5791

8. Ibsrela

9. Rdx5791

10. Wyd79216a6

11. 1234423-95-0 (free Base)

12. 3-((s)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-n-(26-((3-((s)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)sulfonamido)-10,17-dioxo-3,6,21,24-tetraoxa-9,11,16,18-tetraazahexacosyl)benzenesulfonamide

13. N,n'-(10,17,-dioxo-3,6,21,24-tetraoxa-9,11,16,18-tetraazahexacosane-1,26-diyl)bis(((4s)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)

14. Tenapanor [inn]

15. 1-[2-[2-[2-[[3-[(4s)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl]phenyl]sulfonylamino]ethoxy]ethoxy]ethyl]-3-[4-[2-[2-[2-[[3-[(4s)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl]phenyl]sulfonylamino]ethoxy]ethoxy]ethylcarbamoylamino]butyl]urea

16. Tenapanor [usan:inn]

17. Unii-wyd79216a6

18. Khk-7791

19. Tenapanor [mi]

20. Tenapanor (usan/inn)

21. Tenapanor [usan]

22. Tenapanor [who-dd]

23. Gtpl8449

24. Chembl3304485

25. Schembl15267600

26. Dtxsid40154016

27. Khk7791

28. Bdbm381823

29. Rdx013 Component Tenapanor

30. Bcp24892

31. Bcp28554

32. Ex-a2506

33. Rdx-013 Component Tenapanor

34. Mfcd28386333

35. Tenapanor; Azd1722; Rdx5791

36. Us10272079, Compound 002

37. Us10272079, Compound 180

38. Akos037648586

39. Tenapanor Component Of Rdx013

40. Cs-6273

41. Db11761

42. Tenapanor Component Of Rdx-013

43. Ac-36104

44. Bs-14732

45. Bt178667

46. Hy-15991

47. J3.655.031g

48. D11652

49. A929505

50. Q17122912

51. Azd 1722;azd1722;azd-1722;rdx5791;rdx 5791;rdx-5791

52. Azd-1722; Azd 1722; Azd1722; Rdx 5791; Rdx-5791; Rdx5791

53. 12,15-dioxa-2,7,9-triazaheptadecanamide, 17-(((3-((4s)-6,8-dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenyl)sulfonyl)amino)-n-(2-(2-(2-(((3-((4s)-6,8-dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenyl)sulfonyl)amino)ethoxy)ethoxy)ethyl)-8-oxo-

54. 17-[[[3-[(4s)-6,8-dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl]phenyl]sulfonyl]amino]-n-[2-[2-[2-[[[3-[(4s)-6,8-dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl]phenyl]sulfonyl]amino]ethoxy]ethoxy]ethyl]-8-oxo-12,15-dioxa-2,7,9-triazaheptadecanamide

2.4 Create Date

2013-07-08

3 Chemical and Physical Properties

Molecular Formula	C₅₀H₆₆Cl₄N₈O₁₀S₂
Molecular Weight	1145.0 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	29
Exact Mass	1144.306793 g/mol
Monoisotopic Mass	1142.309743 g/mol
Topological Polar Surface Area	235 Å²
Heavy Atom Count	74
Formal Charge	0
Complexity	1770
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Tenapanor is indicated for the treatment of constipation-predominant irritable bowel syndrome (IBS-C) in adults. It is also currently being investigated as a treatment for hyperphosphatemia in chronic kidney disease patients undergoing dialysis (NCT02081534 and NCT02675998).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Through the inhibition of dietary sodium absorption tenapanor causes an increase in water secretion into the intestines, thereby decreasing transit time and softening stool consistency.

5.2 ATC Code

A - Alimentary tract and metabolism

A06 - Drugs for constipation

A06A - Drugs for constipation

A06AX - Other drugs for constipation

A06AX08 - Tenapanor

5.3 Absorption, Distribution and Excretion

Absorption

Tenapanor undergoes very minimal systemic absorption following oral administration. During clinical trials, plasma concentrations were below the limit of quantitation (i.e. less than 0.5 ng/mL) in the majority of samples from healthy subjects - for this reason, typical pharmacokinetic values related to absorption such as AUC and C_max were unable to be ascertained. The effects of tenapanor are greatest when administered 5 to 10 minutes before meals.

Route of Elimination

Following administration of a radio labeled dose of tenapanor, 70% of the radioactivity was excreted in the feces within 120 hours of administration and 79% within 240 hours. Approximately 65% of the total dose is excreted as unchanged parent drug within 144 hours of administration. Only 9% of the administered dose was found in the urine, existing primarily as metabolites. Tenapanor's M1 metabolite is excreted unchanged in the urine and accounts for approximately 1.5% of the total dose within 144 hours of administration.

5.4 Metabolism/Metabolites

The majority of tenapanor's metabolism to its primary metabolite, M1, is catalyzed via CYP3A4/5. Exposure of tenapanor to hepatic CYP enzymes is likely limited due to its minimal systemic absorption, so its metabolism may be due to intestinal CYP enzyme activity. The M1 metabolite of tenapanor is a P-glycoprotein substrate and, in contrast to its parent drug, can be detected in plasma, reaching a C_max of approximately 15 ng/mL at steady state. It is not considered active against NHE3.

5.5 Biological Half-Life

Tenapanor's FDA label states that its half-life could not be determined during clinical trials due to its minimal systemic absorption resulting in plasma concentrations below the limit of quantitation (i.e. less than 0.5 ng/mL).

5.6 Mechanism of Action

Tenapanor is a locally-acting small molecule inhibitor of the sodium/hydrogen exchanger isoform 3 (NHE3), an antiporter expressed on the apical surface of enterocytes in the small intestine and colon which is involved in sodium-fluid homeostasis. By inhibiting this antiporter tenapanor causes retention of sodium within the lumen of the intestine - this results in an osmotic gradient that draws water into the lumen and softens stool consistency. There is some evidence that tenapanor can inhibit the uptake of dietary phosphorus in the gastrointestinal tract, though the exact mechanism of this activity has yet to be elucidated.

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