Flerobuterol

Flerobuterol

File:Flerobuterol.svg
Clinical data
Other names	CRL-40827
Drug class	β-Adrenergic receptor agonist
Identifiers
IUPAC name 2-(tert-butylamino)-1-(2-fluorophenyl)ethanol
CAS Number	82101-10-8
PubChem CID	71254
ChemSpider	64385
UNII	F05RR5M463
ChEMBL	ChEMBL2106772
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C12H18FNO
Molar mass	211.280 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)NCC(C1=CC=CC=C1F)O
InChI InChI=1S/C12H18FNO/c1-12(2,3)14-8-11(15)9-6-4-5-7-10(9)13/h4-7,11,14-15H,8H2,1-3H3 Key:XTJMTDZHCLBKFU-UHFFFAOYSA-N

Flerobuterol (INNTooltip International Nonproprietary Name; developmental code name CRL-40827) is a selective β-adrenergic receptor agonist related to salbutamol which was under development for the treatment of major depressive disorder but was never marketed. It is an agonist of the β₁-, β₂-, and β₃-adrenergic receptors. The drug was under development in France by Cephalon and Lafon and reached phase 2 clinical trials prior to its development being discontinued. It was first described in the scientific literature by 1988 and its development was terminated in 2007.

Synthesis

The chemical synthesis of flerobuterol was reported:

File:Flerobuterol synthesis.svg

The halogenation of 2'-fluoroacetophenone [445-27-2] (1) with molecular bromine in acetic acid led to 2-Fluorophenacyl bromide [655-15-2] (2). Alkylation with tert-butylamine [75-64-9] led to 2-(tert-butylamino)-1-(2-fluorophenyl)ethenone, PC13374926 (3). The reduction of the ketone with sodium borohydride led to Flerobuterol (4).