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Velusetrag

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Also known as: Td-5108, 866933-46-2, J4vnv64arb, 1,2-dihydro-n-[(3-endo)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]oct-3-yl]-1-(1-methylethyl)-2-oxo-3-quinolinecarboxamide, 3-quinolinecarboxamide, 1,2-dihydro-n-((3-endo)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-, Td 5108

Molecular Formula

C₂₅H₃₆N₄O₅S

Molecular Weight

504.6 g/mol

InChI Key

HXLOHDZQBKCUCR-VTHDOGFWSA-N

FDA UNII

J4VNV64ARB

Velusetrag has been used in trials studying the treatment of Gastroparesis and Alzheimer's Disease. It is a highly selective serotonin receptor agonist effective in patients with chronic constipation. It is being developed by Theravance. Velusetrag was discovered by Theravance through the application of its multivalent drug design in a research program dedicated to finding new treatments for GI motility disorders.

1 2D Structure

Velusetrag

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(1S,5R)-8-[(2R)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide

2.1.2 InChI

InChI=1S/C25H36N4O5S/c1-16(2)29-23-8-6-5-7-17(23)11-22(25(29)32)24(31)26-18-12-19-9-10-20(13-18)28(19)15-21(30)14-27(3)35(4,33)34/h5-8,11,16,18-21,30H,9-10,12-15H2,1-4H3,(H,26,31)/t18?,19-,20+,21-/m0/s1

2.1.3 InChI Key

HXLOHDZQBKCUCR-VTHDOGFWSA-N

2.1.4 Canonical SMILES

CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3CC4CCC(C3)N4CC(CN(C)S(=O)(=O)C)O

2.1.5 Isomeric SMILES

CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3C[C@H]4CC[C@@H](C3)N4C[C@H](CN(C)S(=O)(=O)C)O

2.2 Other Identifiers

2.2.1 UNII

J4VNV64ARB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid ((1s,3r,5r)-8-((r)-2-hydroxy-3-(methanesulfonyl-methyl-amino)propyl)-8-aza-bicyclo(3.2.1)oct-3-yl)amide

2. Td-5108

3. Td5108

2.3.2 Depositor-Supplied Synonyms

1. Td-5108

2. 866933-46-2

3. J4vnv64arb

4. 1,2-dihydro-n-[(3-endo)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]oct-3-yl]-1-(1-methylethyl)-2-oxo-3-quinolinecarboxamide

5. 3-quinolinecarboxamide, 1,2-dihydro-n-((3-endo)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-

6. Td 5108

7. Velusetrag [usan]

8. Velusetrag [inn]

9. Unii-j4vnv64arb

10. Velusetrag [usan:inn]

11. Velusetrag [who-dd]

12. Gtpl8425

13. Schembl2917361

14. Chembl2087337

15. Dtxsid001029768

16. Serotonin 5-ht4 Receptor Agonists

17. Bdbm50391069

18. Zinc15821733

19. Compound 15 [pmid 22959244]

20. Db12702

21. Hy-10457

22. Cs-0002610

23. E98885

24. N-((1r,3r,5s)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8- Azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

25. N-((1r,3r,5s)-8-((2r)-2-hydroxy-3-(methyl(methylsulfonyl)amino)propyl)-8-azabicyclo(3.2.1)oct-3-yl)-1-(1-methylethyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

26. N-[(1r,5s)-8-[(2r)-2-hydroxy-3-(methyl-methylsulfonylamino)propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide

27. N-[(1s,5r)-8-[(2r)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide

2.4 Create Date

2006-11-06

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₆N₄O₅S
Molecular Weight	504.6 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	504.24064144 g/mol
Monoisotopic Mass	504.24064144 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	932
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Pharmacology

Studies demonstrating the in vivo preclinical profile of Velusetrag showed that the compound has potent 5-HT4 receptor agonist activity by several routes of administration, including oral, providing robust prokinetic activity in the digestive tract of three different animal species, consistent with its highly potent and selective 5-HT4 receptor agonist in vitro profile.

4.2 Mechanism of Action

Velusetrag is a potent, highly selective agonist with high intrinsic activity at the 5-HT4 receptor. Relative to other 5-HT receptor types, Velusetrag is > 500-fold selective for binding to the human 5-HT4 receptor. Theravance anticipates that the high degree of selectivity of Velusetrag provides the potential for it to be a better and safer medicine for the treatment of patients with severe constipation and possibly constipation predominant irritable bowel syndrome.

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