Amibegron

Amibegron
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Development terminated;
Identifiers
	IUPAC name Ethyl ([(7S)-7-([(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy)acetate;
CAS Number	121524-08-1 ; HCl: 121524-09-2 ;
PubChem CID	3035442;
IUPHAR/BPS	568;
ChemSpider	108738 ;
UNII	PDQ3ME68U3; HCl: N910CJ679E ;
KEGG	D08851 ;
ChEMBL	ChEMBL545437 ;
CompTox Dashboard (EPA)	DTXSID6047361 ;
Chemical and physical data
Formula	C22H26ClNO4
Molar mass	403.90 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)COc3ccc1CCC(Cc1c3)NCC(O)c2cc(Cl)ccc2;
	InChI 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 ; Key:NQIZCDQCNYCVAS-RQBPZYBGSA-N ;
	(verify)

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.^[1]^[2]

On July 31, 2008, Sanofi-Aventis announced that it has decided to discontinue development of amibegron.^[3]

References

^ Stemmelin J, Cohen C, Terranova JP, Lopez-Grancha M, Pichat P, Bergis O, et al. (February 2008). "Stimulation of the beta3-Adrenoceptor as a novel treatment strategy for anxiety and depressive disorders". Neuropsychopharmacology. 33 (3): 574–87. doi:10.1038/sj.npp.1301424. PMID 17460614.
^ Overstreet DH, Stemmelin J, Griebel G (June 2008). "Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression". Pharmacology, Biochemistry, and Behavior. 89 (4): 623–6. doi:10.1016/j.pbb.2008.02.020. PMID 18358519. S2CID 35026036.
^ Second quarter 2008 results. July 31, 2008, retrieved March 9, 2009.

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	Development terminated
Identifiers
IUPAC name Ethyl ([(7S)-7-([(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy)acetate
CAS Number	121524-08-1^Y HCl: 121524-09-2^Y
PubChem CID	3035442
IUPHAR/BPS	568
ChemSpider	108738^Y
UNII	PDQ3ME68U3 HCl: N910CJ679E^Y
KEGG	D08851^Y
ChEMBL	ChEMBL545437^Y
CompTox Dashboard (EPA)	DTXSID6047361
Chemical and physical data
Formula	C₂₂H₂₆ClNO₄
Molar mass	403.90 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC(=O)COc3ccc1CCC(Cc1c3)NCC(O)c2cc(Cl)ccc2
InChI 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^Y Key:NQIZCDQCNYCVAS-RQBPZYBGSA-N^Y
(verify)