Radafaxine

Radafaxine

Systematic (IUPAC) name
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
Identifiers
CAS Number	106083-71-0 N
ATC code	none
PubChem	CID: 9795056
ChemSpider	7970823 Y
UNII	Q47741214K Y
ChEMBL	CHEMBL1172928 Y
Chemical data
Formula	C13H18ClNO2
Molecular mass	292.20 g/mol
SMILES Clc1cccc(c1)[C@]2(O)OCC(N[C@H]2C)(C)C
InChI InChI=1S/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3/t9-,13+/m0/s1 Y Key:RCOBKSKAZMVBHT-TVQRCGJNSA-N Y
NY (what is this?)  (verify)

Radafaxine is drug candidate designated GW-353,162 by GlaxoSmithKline, investigated for treatment of restless leg syndrome and as an NDRI antidepressant. GlaxoSmithKline was targeting Radafaxine for regulatory filing in 2007, but development was discontinued in 2006 due to "poor test results".

Chemistry

It is a potent metabolite of bupropion, the compound in GlaxoSmithKline's Wellbutrin. More specifically, "hydroxybupropion" is an analogue of bupropion, and radafaxine is an isolated isomer ((2S,3S)-) of hydroxybupropion.

Therefore, radafaxine builds on at least some of the properties of bupropion in humans.

Effects

In various clinical trials, radafaxine has been studied as a treatment for clinical depression, obesity, and neuropathic pain. Radafaxine is described as a norepinephrine-dopamine reuptake inhibitor (NDRI).

Unlike bupropion (which has a much higher effect on dopamine reuptake), radafaxine seems to have a higher potency on norepinephrine. Radafaxine has about 70% of bupropion's efficacy in blocking dopamine reuptake, and 392% of efficacy in blocking norepinephrine reuptake, making it fairly selective for inhibiting the reuptake of norepinephrine over dopamine. This, according to GlaxoSmithKline, may account for the increased effect of radafaxine on pain and fatigue.

At least one study suggests that radafaxine has a low abuse potential similar to bupropion.

See also

• Manifaxine
• Phenmetrazine
• G-130
• 2-Phenyl-3,6-dimethylmorpholine