VELUSETRAG HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H36N4O5S.ClH
Molecular Weight	541.103
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)N1C(=O)C(=CC2=CC=CC=C12)C(=O)N[C@@H]3C[C@@H]4CC[C@H](C3)N4C[C@@H](O)CN(C)S(C)(=O)=O

InChI

InChIKey=BLIKSWRONBYRDD-ULYYJTHRSA-N

InChI=1S/C25H36N4O5S.ClH/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);1H/t18-,19+,20-,21-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C25H36N4O5S
Molecular Weight	504.642
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19691492 | https://www.ncbi.nlm.nih.gov/pubmed/18408918

Velusetrag (TD-5108) is a potent, selective high intrinsic activity serotonin 5-HT(4) receptor agonist. Velusetrag has achieved proof-of-concept in patients with chronic idiopathic constipation and was on phase II of clinical trial for the treatment of Alzheimer's disease and constipation, when studies were discontinued. In addition, velusetrag is on the phase II of clinical trial for the treatment of gastroparesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 4 8 Target ID: Q13639\|\|\|Q9NY73 Gene ID: 3360.0 Gene Symbol: HTR4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18408918	Agonist 2678		8.3 null [pEC50]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://clinicaltrials.gov/ct2/show/NCT01467726	Primary	Phase II 1132	Unknown Approved Use Unknown
Constipation 112 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19691492	Primary	Phase II 1132	Unknown Approved Use Unknown
Gastroparesis 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02267525	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Axon MedChem	2060	https://www.axonmedchem.com/product/2060
Compound Cloud	53297466
Compound Cloud	53297467
MolPort	MolPort-042-665-805	https://www.molport.com/shop/molecule-link/MolPort-042-665-805
Molnova	M16300	https://www.molnova.com/en/serch-list.html?keywords=M16300
MuseChem	I010011	https://www.musechem.com/product/I010011.html
Norris Pharm	NSZB-A152899
Ryan Scientific	101-94043	https://ryansci.com/products?q=101-94043&list_q=&search_type=exact
eMolecules	275088212	https://orderbb.emolecules.com/search/#?query=275088212
eMolecules	300875059	https://orderbb.emolecules.com/search/#?query=300875059
eMolecules	46024431	https://orderbb.emolecules.com/search/#?query=46024431

PubMed

Title	Date	PubMed
Participation of 5-HT3, 5-HT4, and nicotinic receptors in the peristaltic reflex of guinea pig distal colon.	1996 Nov	8944700
Signal transduction pathways for serotonin as an intestinal secretagogue.	1997 Oct	9366057
Serotonin: a mediator of the brain-gut connection.	2000 Oct	11051338
The in vitro pharmacological profile of TD-5108, a selective 5-HT(4) receptor agonist with high intrinsic activity.	2008 Jul	18415081
New-generation 5-HT4 receptor agonists: potential for treatment of gastrointestinal motility disorders.	2010 Jun	20408739
Discovery, oral pharmacokinetics and in vivo efficacy of velusetrag, a highly selective 5-HT(4) receptor agonist that has achieved proof-of-concept in patients with chronic idiopathic constipation.	2012 Oct 1	22959244
Phase II drugs under clinical investigation for the treatment of chronic constipation.	2014 Nov	24960333

Patents

Sample Use Guides

In Vivo Use Guide

5, 15, 30 or 50 mg Velusetrag (single and 6-day dosing)

Route of Administration: Oral

In Vitro Use Guide

In all in vitro assays, TD-5108 was a high intrinsic activity agonist, unlike tegaserod, mosapride, and cisapride which, in the majority of test systems, had lower intrinsic activity. TD-5108 had high affinity (pK (i) = 7.7) and selectivity (> or =25-fold) for h5-HT(4(c)) receptors over other biogenic amine receptors. TD-5108 was >500-fold selective over other 5-HT receptors (including h5-HT(2B) and h5-HT(3A)) and, at 3 uM, had no effect on human ether-à-go-go-related gene K+ channels.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:02:10 GMT 2023` Edited by `admin` on `Fri Dec 15 16:02:10 GMT 2023`
Record UNII	NF4JCT94PW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VELUSETRAG HYDROCHLORIDE

Official Name

English

VELUSETRAG HCL

Common Name

English

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 hydrochloride

Common Name

English

VELUSETRAG HYDROCHLORIDE [USAN]

Common Name

English

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-, MONOHYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66880

Created by admin on Fri Dec 15 16:02:10 GMT 2023 , Edited by admin on Fri Dec 15 16:02:10 GMT 2023

Code System Code Type Description

CAS

866933-51-9

Created by admin on Fri Dec 15 16:02:10 GMT 2023 , Edited by admin on Fri Dec 15 16:02:10 GMT 2023

PRIMARY

USAN

UU-25

Created by admin on Fri Dec 15 16:02:11 GMT 2023 , Edited by admin on Fri Dec 15 16:02:11 GMT 2023

PRIMARY

FDA UNII

NF4JCT94PW

Created by admin on Fri Dec 15 16:02:10 GMT 2023 , Edited by admin on Fri Dec 15 16:02:10 GMT 2023

PRIMARY

NCI_THESAURUS

C84239

Created by admin on Fri Dec 15 16:02:10 GMT 2023 , Edited by admin on Fri Dec 15 16:02:10 GMT 2023

PRIMARY

ChEMBL

CHEMBL2087337

Created by admin on Fri Dec 15 16:02:10 GMT 2023 , Edited by admin on Fri Dec 15 16:02:10 GMT 2023

PRIMARY

SMS_ID

300000044527

Created by admin on Fri Dec 15 16:02:11 GMT 2023 , Edited by admin on Fri Dec 15 16:02:11 GMT 2023

PRIMARY

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Amount:

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					J4VNV64ARB

VELUSETRAG

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19691492 | https://www.ncbi.nlm.nih.gov/pubmed/18408918

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19691492 | https://www.ncbi.nlm.nih.gov/pubmed/18408918