 | |
| Clinical data | |
|---|---|
| Other names | GW-320,659 |
| Routes of administration | Oral |
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider |
|
| UNII | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C12H15F2NO2 |
| Molar mass | 243.254 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
 N Y (what is this?) (verify) | |
Manifaxine (developmental code nameGW-320,659) is anorepinephrine–dopamine reuptake inhibitor developed byGlaxoSmithKline throughstructural modification ofradafaxine, anisomer ofhydroxybupropion and one of theactive metabolites ofbupropion.[1] Manifaxine was researched for treatment ofattention deficit hyperactivity disorder (ADHD) andobesity and was found to be safe, reasonably effective, and well-tolerated for both applications.[2][3] However, no results were reported following these initial trials and development was discontinued.[1]
TheGrignard reaction between 3,5-difluorobenzonitrile (1) and ethylmagnesium bromide gives 3,5-difluoropropiophenone (2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone (3). Intermolecular ring formation withDL-alaninol (2-aminopropanol) completes the synthesis of manifaxine (4).
