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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26ClNO4
Molecular Weight 403.8999
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIBEGRON

SMILES

CCOC(=O)COc1ccc2CC[C@@]([H])(Cc2c1)NC[C@@]([H])(c3cccc(c3)Cl)O

InChI

InChIKey=RDJQCOBTKKAQAH-FPOVZHCZSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H26ClNO4
Molecular Weight 403.8999
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1976401 | https://www.ncbi.nlm.nih.gov/pubmed/14584972

Amibegron (SR 58611A or SR 58611) is a highly selective agonist for atypical beta3-adrenoceptors. It stimulates neuronal activity in a specific area of the prefrontal cortex and also inhibits intestinal motility. Amibegron was in phase III trials worldwide for the treatment of depression and generalised anxiety disorder but development of the product was discontinued in 2008. Amibegron has been tested for its potential as a treatment for irritable bowel syndrome.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro inhibition of intestinal motility by phenylethanolaminotetralines: evidence of atypical beta-adrenoceptors in rat colon.
1990 Aug
Antidepressant profile in rodents of SR 58611A, a new selective agonist for atypical beta-adrenoceptors.
1992 Aug 25
Stimulation of the beta3-Adrenoceptor as a novel treatment strategy for anxiety and depressive disorders.
2008 Feb
Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression.
2008 Jun
Implication of beta3-adrenoceptors in the antidepressant-like effects of amibegron using Adrb3 knockout mice in the chronic mild stress.
2010 Jan 20
Patents

Sample Use Guides

This eight week double-blind phase III trial compared the efficacy of paroxetine with two fixed doses of amibegron (175mg or 350mg q12) in treating the symptoms of depression (NCT00385307). In 24 healthy obese volunteers, amibegron 60 and 180 mg/day tid for 6 days and a single dose on day 7 was safe and well tolerated.
Route of Administration: Oral
In Vitro Use Guide
Amibegron (SR 58611A or SR 58611) increased cyclic AMP levels in membrane homogenates from rat interscapular brown adipose tissue with an EC50 of 20 nM. This compound also stimulated glycerol release from the brown fat cells, with an EC50 of 11 nM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:22:00 UTC 2021
Edited
by admin
on Sat Jun 26 04:22:00 UTC 2021
Record UNII
PDQ3ME68U3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMIBEGRON
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
AMIBEGRON [WHO-DD]
Common Name English
AMIBEGRON [USAN]
Common Name English
SR58611
Code English
AMIBEGRON [INN]
Common Name English
ACETIC ACID, (((7S)-7-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)-5,6,7,8-TETRAHYDRO-2-NAPHTHALENYL)OXY)-, ETHYL ESTER
Common Name English
ETHYL (((7S)-7-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)-5,6,7,8-TETRAHYDRONAPHTHALEN-2-YL)OXY)ACETATE
Systematic Name English
SR-58611
Code English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1193948
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
PUBCHEM
3035442
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
INN
8687
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
WIKIPEDIA
AMIBEGRON
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
DRUG BANK
DB05395
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
FDA UNII
PDQ3ME68U3
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
NCI_THESAURUS
C77932
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
MESH
C076252
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
CAS
121524-08-1
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
EPA CompTox
121524-08-1
Created by admin on Sat Jun 26 04:22:00 UTC 2021 , Edited by admin on Sat Jun 26 04:22:00 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY