amibegron

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 437193151

| IUPAC_name = Ethyl ([(7S)-7-([(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy)acetate

| image = Amibegron.svg

| width = 250

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Development terminated

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 121524-08-1

| index2_label = HCl

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 121524-09-2

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = N910CJ679E

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3035442

| IUPHAR_ligand = 568

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 108738

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = PDQ3ME68U3

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08851

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 545437

| C=22 | H=26 | Cl=1 | N=1 | O=4

| smiles = CCOC(=O)COc3ccc1CCC(Cc1c3)NCC(O)c2cc(Cl)ccc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NQIZCDQCNYCVAS-RQBPZYBGSA-N

}}

Amibegron (SR-58,611A) was a drug developed by Sanofi-Aventis (now Sanofi) which acts as a selective agonist for the β₃ adrenergic receptor. It is the first orally active β₃ agonist developed that is capable of entering the central nervous system, and has antidepressant and anxiolytic effects.{{cite journal | vauthors = Stemmelin J, Cohen C, Terranova JP, Lopez-Grancha M, Pichat P, Bergis O, Decobert M, Santucci V, Françon D, Alonso R, Stahl SM, Keane P, Avenet P, Scatton B, le Fur G, Griebel G | display-authors = 6 | title = Stimulation of the beta3-Adrenoceptor as a novel treatment strategy for anxiety and depressive disorders | journal = Neuropsychopharmacology | volume = 33 | issue = 3 | pages = 574–87 | date = February 2008 | pmid = 17460614 | doi = 10.1038/sj.npp.1301424 | doi-access = free }}{{cite journal | vauthors = Overstreet DH, Stemmelin J, Griebel G | title = Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression | journal = Pharmacology, Biochemistry, and Behavior | volume = 89 | issue = 4 | pages = 623–6 | date = June 2008 | pmid = 18358519 | doi = 10.1016/j.pbb.2008.02.020 | s2cid = 35026036 }}

On July 31, 2008, Sanofi-Aventis announced that it has decided to discontinue development of amibegron.[https://archive.today/20110807103952/http://en.sanofi-aventis.com/press/press_releases/2008/ppc_20376.asp Second quarter 2008 results]. July 31, 2008, retrieved March 9, 2009.