Structure via PubChem · Public domain (PubChem)
amibegron
Sign in to saveAlso known as SR 58611, SR-58,611A, SR-58611A, SR58611A
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.
Chemical data
- Formula
- C22H26ClNO4
- Molecular weight
- 403.9 g/mol
- IUPAC name
- ethyl 2-[[(7S)-7-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]acetate
- SMILES
- CCOC(=O)COC1=CC2=C(CC[C@@H](C2)NC[C@@H](C3=CC(=CC=C3)Cl)O)C=C1
- InChIKey
- RDJQCOBTKKAQAH-FPOVZHCZSA-N
- XLogP
- 3.9
- Polar surface area
- 67.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- anxiety, major depressive disorder, depressive disorder
via ChEMBL · EBI
Research
62 papers- The beta3 adrenoceptor agonist, amibegron (SR58611A) counteracts stress-induced behavioral and neurochemical changes.European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology · 2010
- Preconditioning improves muscle regeneration after ischemia-reperfusion injury.Journal of orthopaedic research : official publication of the Orthopaedic Research Society · 2021
- β(3)-Adrenergic receptor agonist treats rotator cuff fatty infiltration by activating beige fat in mice.Journal of shoulder and elbow surgery · 2021
- Age-dependent decline of B3AR agonist-mediated activation of FAP UCP-1 expression in murine models of chronic rotator cuff repair.Journal of orthopaedic research : official publication of the Orthopaedic Research Society · 2024
- Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression.Pharmacology, biochemistry, and behavior · 2008
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 403.155
Show 5 more facts
- chemical formula
- C₂₂H₂₆ClNO₄
- canonical SMILES
- CCOC(=O)COC1=CC2=C(CCC(C2)NCC(C3=CC(=CC=C3)Cl)O)C=C1
- isomeric SMILES
- CCOC(=O)COC1=CC2=C(CC[C@@H](C2)NC[C@@H](C3=CC(=CC=C3)Cl)O)C=C1
- physically interacts with
- adrenoceptor beta 3
- Commons category
- Amibegron
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
On July 31, 2008, Sanofi-Aventis announced that it has decided to discontinue development of amibegron.
Excerpted from Wikipedia’s “amibegron” article, available under the CC BY-SA 4.0 licence.