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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 C22H26ClNO4
Molecular Weight 403.899
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
N910CJ679E
Record Status Validated (UNII)
Record Version