Velusetrag

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Velusetrag
Accession Number
DB12702  (DB05655)
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
TD-5108
Categories
UNII
J4VNV64ARB
CAS number
866933-46-2
Weight
Average: 504.65
Monoisotopic: 504.240641449
Chemical Formula
C25H36N4O5S
InChI Key
HXLOHDZQBKCUCR-WOZUAGRISA-N
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
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
SMILES
CC(C)N1C(=O)C(=CC2=CC=CC=C12)C(=O)N[C@@H]1C[C@@H]2CC[C@H](C1)N2C[C@@H](O)CN(C)S(C)(=O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics

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.

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.

TargetActionsOrganism
U5-hydroxytryptamine receptor 4Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Overall, the most common adverse events include headache, diarrhea, nausea and vomiting.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11842633
PubChem Substance
347828900
ChemSpider
28527582
BindingDB
50391069
ChEMBL
CHEMBL2087337
ZINC
ZINC000100374472
Wikipedia
Velusetrag

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentChronic Constipation1
2CompletedTreatmentGastroparesis2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.116 mg/mLALOGPS
logP1.4ALOGPS
logP-0.099ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)8.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.26 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.54 m3·mol-1ChemAxon
Polarizability54.83 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as quinoline-3-carboxamides. These are quinolines in which the quinoline ring system is substituted by one carboxamide group at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxamides
Direct Parent
Quinoline-3-carboxamides
Alternative Parents
Hydroquinolones / Hydroquinolines / Tropane alkaloids / Pyridinecarboxylic acids and derivatives / Pyridinones / Benzenoids / N-alkylpyrrolidines / Piperidines / Organosulfonamides / Organic sulfonamides
show 12 more
Substituents
Quinoline-3-carboxamide / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid or derivatives / Tropane alkaloid / Pyridinone / Organic sulfonic acid amide / Organosulfonic acid amide / Piperidine / N-alkylpyrrolidine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR4
Uniprot ID
Q13639
Uniprot Name
5-hydroxytryptamine receptor 4
Molecular Weight
43760.975 Da

Drug created on October 20, 2016 17:41 / Updated on March 01, 2020 21:17

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