Velusetrag

Velusetrag

Systematic (IUPAC) name
N-{(1R,3r,5S)-8-[(2R)-2-Hydroxy-3-(N-methylmethanesulfonamido)propyl]-8-azabicyclo[3.2.1]octan-3-yl}-2-oxo-1-(propan-2-yl)-1,2-dihydroquinoline-3-carboxamide
Clinical data
Routes of administration	Oral
Legal status
Legal status	Investigational drug
Identifiers
CAS Number	866933-46-2 866933-51-9 (hydrochloride)
ATC code	None
PubChem	CID 53297466
IUPHAR/BPS	8425
ChemSpider	28527582
UNII	J4VNV64ARB
KEGG	D09693
ChEMBL	CHEMBL2087337
Synonyms	N-[(3-endo)-8-{(2R)-2-Hydroxy-3-[methyl(methylsulfonyl)amino]propyl}-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide
Chemical data
Formula	C25H36N4O5S
Molar mass	504.65 g·mol^−1
SMILES CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)N[C@H]3C[C@H]4CC[C@@H](C3)N4C[C@H](CN(C)S(=O)(=O)C)O
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 Key:HXLOHDZQBKCUCR-WOZUAGRISA-N

Velusetrag (INN,^[1] USAN; previously known as TD-5108) is an experimental drug candidate for the treatment of gastroparesis, chronic constipation and irritable bowel syndrome.^[2] It is a potent, selective, high efficacy 5-HT₄ receptor agonist.^[3] In clinical trials, velusetrag was efficacious and well tolerated in patients with chronic constipation,^[4] and showed accelerated intestinal and colonic transit after single dosing and accelerated gastric emptying after multiple dosing.^[5]

As of August 31, 2015, clinical trials for chronic constipation and Alzheimer's disease seem to be terminated.^[6] One study exploring the efficacy and safety of velusetrag in idiopathic or diabetic gastroparesis is recruiting participants.^[7]

See also

• Prucalopride

References

1. "WHO Drug Information, Vol. 24, No. 1, 2010. International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 63" (PDF). World Health Organization. p. 79. Retrieved 26 April 2016.
2. M. Vazquez-Roque, and M. Camilleri (2011). "Velusetrag". Drugs of the Future 36 (6): 447–454. doi:10.1358/dof.2011.36.6.1594078 (inactive 2015-02-01).
3. Smith, JA; Beattie, DT; Marquess, D; Shaw, JP; Vickery, RG; Humphrey, PP (2008). "The in vitro pharmacological profile of TD-5108, a selective 5-HT(4) receptor agonist with high intrinsic activity". Naunyn-Schmiedeberg's archives of pharmacology 378 (1): 125–37. doi:10.1007/s00210-008-0282-y. PMID 18415081.
4. Goldberg, M; Li, YP; Johanson, JF; Mangel, AW; Kitt, M; Beattie, DT; Kersey, K; Daniels, O (2010). "Clinical trial: The efficacy and tolerability of velusetrag, a selective 5-HT4 agonist with high intrinsic activity, in chronic idiopathic constipation - a 4-week, randomized, double-blind, placebo-controlled, dose-response study". Alimentary pharmacology & therapeutics 32 (9): 1102–12. doi:10.1111/j.1365-2036.2010.04456.x. PMID 21039672.
5. Manini, ML; Camilleri, M; Goldberg, M; Sweetser, S; McKinzie, S; Burton, D; Wong, S; Kitt, MM; et al. (2010). "Effects of Velusetrag (TD-5108) on gastrointestinal transit and bowel function in health and pharmacokinetics in health and constipation". Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 22 (1): 42–9, e7–8. doi:10.1111/j.1365-2982.2009.01378.x. PMC 2905526. PMID 19691492.
6. "Velusetrag — AdisInsight". Springer International Publishing AG. Retrieved 26 April 2016.
7. "The Diabetic and Idiopathic Gastroparesis Efficacy, Safety, and Tolerability (DIGEST) Study". ClinicalTrials.gov. Retrieved 26 April 2016.