Radafaxine
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| ATC code | none |
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| CAS Number | 106083-71-0  |
| PubChem (CID) | 9795056 |
| ChemSpider | 7970823  |
| UNII | Q47741214K |
| ChEMBL | CHEMBL1172928 |
| Chemical and physical data | |
| Formula | C13H18ClNO2 |
| Molar mass | 292.20 g/mol |
| 3D model (Jmol) | Interactive image |
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Radafaxine is drug candidate designated GW-353,162[1] by GlaxoSmithKline, investigated for treatment of restless leg syndrome and as an NDRI antidepressant. GlaxoSmithKline was targeting Radafaxine for regulatory filing in 2007,[2] but development was discontinued in 2006 due to "poor test results".[3]
Contents
Chemistry[edit]
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.[4]
Therefore, radafaxine builds on at least some of the properties of bupropion in humans.[5]
Effects[edit]
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.[6][7] This, according to GlaxoSmithKline, may account for the increased effect of radafaxine on pain and fatigue.[8]
At least one study suggests that radafaxine has a low abuse potential similar to bupropion.[9]
See also[edit]
References[edit]
- ^ Restless Legs Syndrome: First Approval
- ^ {1} Reviews Novel Therapeutics For CNS Disorders And Confirms Strong Pipeline Momentum - News, Search Jobs, Events
- ^ Independent.co.uk: GSK breakthrough on bird flu vaccine.
- ^ radafaxine at the US National Library of Medicine Medical Subject Headings (MeSH)
- ^ GlaxoSmithKline Reviews Novel Therapeutics for CNS Disorders and Confirms Strong Pipeline Momentum
- ^ Xu H, Loboz KK, Gross AS, McLachlan AJ (2007). "Stereoselective analysis of hydroxybupropion and application to drug interaction studies". Chirality. 19 (3): 163–70. doi:10.1002/chir.20356. PMID 17167747.
- ^ Bondarev ML, Bondareva TS, Young R, Glennon RA (2003). "Behavioral and biochemical investigations of bupropion metabolites". Eur J Pharmacol. 474 (1): 85–93. doi:10.1016/S0014-2999(03)02010-7. PMID 12909199.
- ^ Microsoft PowerPoint - slides_05_burch.ppt
- ^ Radafaxine
