 | |
| Clinical data | |
|---|---|
| Other names | (S,S)-Hydroxybupropion; (2S,3S)-Hydroxybupropion; GW-353,162 |
| Routes of administration | Oral |
| ATC code |
|
| Identifiers | |
| |
| CAS Number |
|
| PubChemCID | |
| ChemSpider |
|
| UNII |
|
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C13H18ClNO2 |
| Molar mass | 255.74 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
 N Y (what is this?) (verify) | |
Radafaxine (developmental codeGW-353,162; also known as(2S,3S)-hydroxybupropion or(S,S)-hydroxybupropion[1]) is anorepinephrine–dopamine reuptake inhibitor (NDRI) which was under development byGlaxoSmithKline in the 2000s for a variety of different indications but was never marketed.[2] These uses included treatment ofrestless legs syndrome,major depressive disorder,bipolar disorder,neuropathic pain,fibromyalgia, andobesity.[2] Regulatory filing was planned for 2007,[3] but development was discontinued in 2006 due to "poor test results".[4]
Radafaxine is described as anorepinephrine–dopamine reuptake inhibitor (NDRI). In contrast to bupropion, it appears to have a higherpotency on inhibition ofnorepinephrine reuptake than ondopamine reuptake. Radafaxine has about 70% of the efficacy of bupropion in blocking dopamine reuptake, and 392% of efficacy in blocking norepinephrine reuptake, making it fairlyselective for inhibiting the reuptake of norepinephrine over dopamine.[5][6] This, according to GlaxoSmithKline, may account for the increased effect of radafaxine onpain andfatigue.[7] At least one study suggests that radafaxine has a lowabuse potential similar to bupropion.[8]
Radafaxine is a potentmetabolite ofbupropion, the compound in GlaxoSmithKline'sWellbutrin. More specifically,hydroxybupropion is a major metabolite of bupropion that is further metabolized via anintramolecular cyclization to give radafaxine as the (2S,3S) isomer,[9] as well as the corresponding(2R,3R) isomer isomer, which is less pharmacologically active as amonoamine reuptake inhibitor than radafaxine.[10][11][12]Manifaxine (GW-320,659) was developed as an analogue of radafaxine and has been studied for the treatment of ADHD and obesity.[13][14]
Media related toRadafaxine at Wikimedia Commons