Amibegron

Identification

Name
Amibegron
Accession Number
DB05395
Type
Small Molecule
Groups
Investigational
Description

Amibegron is an agonist for atypical beta3-adrenoceptors which inhibits intestinal motility.

Structure
Thumb
Synonyms
Not Available
External IDs
SR 58611 / SR-58611 / SR58611
Categories
UNII
PDQ3ME68U3
CAS number
Not Available
Weight
Average: 403.9
Monoisotopic: 403.155036
Chemical Formula
C22H26ClNO4
InChI Key
RDJQCOBTKKAQAH-FPOVZHCZSA-N
InChI
InChI=1S/C22H26ClNO4/c1-2-27-22(26)14-28-20-9-7-15-6-8-19(11-17(15)12-20)24-13-21(25)16-4-3-5-18(23)10-16/h3-5,7,9-10,12,19,21,24-25H,2,6,8,11,13-14H2,1H3/t19-,21-/m0/s1
IUPAC Name
ethyl 2-{[(7S)-7-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}acetate
SMILES
CCOC(=O)COC1=CC=C2CC[C@@H](CC2=C1)NC[C@H](O)C1=CC=CC(Cl)=C1

Pharmacology

Indication

Investigated for use/treatment in depression, irritable bowel syndrome (IBS), and obesity.

Pharmacodynamics
Not Available
Mechanism of action

SR 58611 has positive chronotropic effect which is mainly of peripheral origin and can be attributed to a baroreceptor-mediated reflex due to the beta3-adrenoceptor mediated vasodilation with an increase in sympathetic tone and a reduction in vagal tone to the heart.

TargetActionsOrganism
UBeta-3 adrenergic receptorNot AvailableHuman
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
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe therapeutic efficacy of Amibegron can be decreased when used in combination with Acebutolol.
AcepromazineAcepromazine may decrease the vasoconstricting activities of Amibegron.
AlfuzosinThe therapeutic efficacy of Amibegron can be decreased when used in combination with Alfuzosin.
AmitriptylineThe therapeutic efficacy of Amibegron can be decreased when used in combination with Amitriptyline.
AmoxapineAmoxapine may decrease the vasoconstricting activities of Amibegron.
AripiprazoleAripiprazole may decrease the vasoconstricting activities of Amibegron.
AsenapineAsenapine may decrease the vasoconstricting activities of Amibegron.
AtenololThe therapeutic efficacy of Amibegron can be decreased when used in combination with Atenolol.
Benzylpenicilloyl PolylysineAmibegron may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetaxololThe therapeutic efficacy of Amibegron can be decreased when used in combination with Betaxolol.
Food Interactions
Not Available

References

General References
  1. Authors unspecified: SR 58611A: SR 58611. Drugs R D. 2003;4(6):380-2. [PubMed:14584972]
  2. Montastruc JL, Verwaerde P, Pelat M, Galitzky J, Langin D, Lafontan M, Berlan M: Peripheral cardiovascular actions of SR 58611 A, a beta 3-adrenoceptor agonist, in the dog: lack of central effect. Fundam Clin Pharmacol. 1999;13(2):180-6. [PubMed:10226761]
External Links
PubChem Compound
3035442
PubChem Substance
347827725
ChemSpider
2299682
ChEMBL
CHEMBL1193948
Wikipedia
Amibegron

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMajor Depressive Disorder (MDD)4

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00179 mg/mLALOGPS
logP3.91ALOGPS
logP3.89ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.79 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity109.09 m3·mol-1ChemAxon
Polarizability44.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenoxyacetic acid derivatives
Direct Parent
Phenoxyacetic acid derivatives
Alternative Parents
Tetralins / Phenol ethers / Alkyl aryl ethers / Chlorobenzenes / Aralkylamines / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters
show 7 more
Substituents
Phenoxyacetate / Tetralin / Phenol ether / Alkyl aryl ether / Chlorobenzene / Aralkylamine / Halobenzene / Aryl chloride / Aryl halide / 1,2-aminoalcohol
show 21 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da

Drug created on November 18, 2007 11:24 / Updated on August 02, 2018 05:30