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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26ClNO4.ClH
Molecular Weight 440.36
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIBEGRON HYDROCHLORIDE

SMILES

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

InChI

InChIKey=NQIZCDQCNYCVAS-RQBPZYBGSA-N
InChI=1S/C22H26ClNO4.ClH/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;1H/t19-,21-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
SR 58611A: SR 58611.
2003
Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression.
2008 Jun
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 Wed Jul 05 23:14:37 UTC 2023
Edited
by admin
on Wed Jul 05 23:14:37 UTC 2023
Record UNII
N910CJ679E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMIBEGRON HYDROCHLORIDE
USAN  
USAN  
Official Name English
SR-58611A
Code English
SR58611A
Code English
Ethyl {[(7S)-7-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}acetate hydrochloride
Systematic Name English
AMIBEGRON HCL
Common Name English
ACETIC ACID, (((7S)-7-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)-5,6,7,8-TETRAHYDRO-2-NAPHTHALENYL)OXY)-, ETHYL ESTER, HYDROCHLORIDE
Common Name English
AMIBEGRON HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
Code System Code Type Description
PUBCHEM
121888
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1193948
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT002941
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
NCI_THESAURUS
C97276
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
FDA UNII
N910CJ679E
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
CAS
121524-09-2
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID20923848
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
SMS_ID
100000175016
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
USAN
UU-12
Created by admin on Wed Jul 05 23:14:37 UTC 2023 , Edited by admin on Wed Jul 05 23:14:37 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY