NAV

Amibegron

Identification

Generic Name
Amibegron
DrugBank Accession Number
DB05395
Background

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

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 403.9
Monoisotopic: 403.155036
Chemical Formula
C22H26ClNO4
Synonyms
  • Amibegron
External IDs
  • SR 58611
  • SR-58611
  • SR58611
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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 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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcebutololThe therapeutic efficacy of Amibegron can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Amibegron is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Amibegron is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Amibegron.
AclidiniumThe risk or severity of Tachycardia can be increased when Amibegron is combined with Aclidinium.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Amibegron hydrochlorideN910CJ679E121524-09-2NQIZCDQCNYCVAS-RQBPZYBGSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aralkylamine / Aromatic alcohol / Aromatic homopolycyclic compound / Aryl chloride / Aryl halide
show 21 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
PDQ3ME68U3
CAS number
121524-08-1
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
[H][C@](O)(CN[C@@]1([H])CCC2=C(C1)C=C(OCC(=O)OCC)C=C2)C1=CC(Cl)=CC=C1

References

General References
  1. Authors unspecified: SR 58611A: SR 58611. Drugs R D. 2003;4(6):380-2. [Article]
  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. [Article]
PubChem Compound
3035442
PubChem Substance
347827725
ChemSpider
2299682
ChEMBL
CHEMBL1193948
ZINC
ZINC000003797401
Wikipedia
Amibegron

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAnxiety Disorders3
3CompletedTreatmentDepressive Disorder1
3CompletedTreatmentDepressive Disorder / Major Depressive Disorder (MDD)1
3CompletedTreatmentMajor Depressive Disorder (MDD)7
3TerminatedTreatmentAnxiety Disorders2

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
Polarizability43.09 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/MSsplash10-0udu-7009500000-76a87e5e5aa22837fe1f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9027000000-38188a3e42271c1b782d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k96-1119100000-862c50019d3dfc5e9ffb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-9022000000-3d87bac70dea8434d7c2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-6739200000-280ffa839a1d5d13d9e9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9320000000-ffa0bf0c23f69438515a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.86034
predicted
DeepCCS 1.0 (2019)
[M+H]+195.21835
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.59758
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-3 adrenergic receptor
Kind
Protein
Organism
Humans
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 at November 18, 2007 18:24 / Updated at February 21, 2021 18:51