AMIBEGRON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26ClNO4
Molecular Weight	403.899
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)COC1=CC2=C(CC[C@@H](C2)NC[C@H](O)C3=CC=CC(Cl)=C3)C=C1

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	403.899
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800001600
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-3 adrenergic receptor 49 Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1976401 \| https://www.ncbi.nlm.nih.gov/pubmed/14584972	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: http://adisinsight.springer.com/drugs/800001600	Primary		Phase III 656	Unknown Approved Use Unknown
Generalized anxiety disorder 32 Sources: http://adisinsight.springer.com/drugs/800001600	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0015P5	https://www.1pchem.com/search?query=1P0015P5
ApexBio Technology	B7558	https://www.apexbt.com/catalogsearch/result/?q=B7558
Cayman Chemical	11954	http://www.caymanchem.com/app/template/Product.vm/catalog/11954
Chem Scene	CS-0025298	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0025298
MolPort	MolPort-023-277-019	https://www.molport.com/shop/molecule-link/MolPort-023-277-019
MuseChem	I002159	https://www.musechem.com/product/I002159.html
Tocris	3986	https://www.tocris.com/search.php?Type=QuickSearch&Value=3986
Toronto Research Chemicals	S684445	https://www.trc-canada.com/product-detail/?CatNum=S684445
eMolecules	36500859	https://orderbb.emolecules.com/search/#?query=36500859

PubMed

Title	Date	PubMed
In vitro inhibition of intestinal motility by phenylethanolaminotetralines: evidence of atypical beta-adrenoceptors in rat colon.	1990 Aug	1976401
Antidepressant profile in rodents of SR 58611A, a new selective agonist for atypical beta-adrenoceptors.	1992 Aug 25	1358639
SR 58611A: SR 58611.	2003	14584972
Stimulation of the beta3-Adrenoceptor as a novel treatment strategy for anxiety and depressive disorders.	2008 Feb	17460614
Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression.	2008 Jun	18358519
Implication of beta3-adrenoceptors in the antidepressant-like effects of amibegron using Adrb3 knockout mice in the chronic mild stress.	2010 Jan 20	19744528
The beta3 adrenoceptor agonist, amibegron (SR58611A) counteracts stress-induced behavioral and neurochemical changes.	2010 Oct	20537869

Patents

Sample Use Guides

In Vivo Use Guide

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 Dec 16 17:55:12 UTC 2023` Edited by `admin` on `Sat Dec 16 17:55:12 UTC 2023`
Record UNII	PDQ3ME68U3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMIBEGRON

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