Radafaxine

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Radafaxine
Systematic (IUPAC) name
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
Identifiers
CAS number 106083-71-0
ATC code  ?
PubChem 446
Chemical data
Formula C13H18ClNO2 
Mol. mass 255.74 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

Radafaxine is drug candidate designated 353162[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]

[edit] Chemistry

It is a potent metabolite of bupropion, the compound in GlaxoSmithKline's Wellbutrin. More specifically, "hydroxybupropion" is a hydroxy derivative of bupropion, and radafaxine is an isolated isomer of hydroxybupropion.[4]

Therefore, radafaxine builds on at least some of the properties of bupropion in humans.[5]

[edit] Effects

Presently in various clinical trials, radafaxine is being 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 slightly higher effect on dopamine reuptake), radafaxine seems to have a higher potency on norepinephrine. This, according to GlaxoSmithKline, may account for the increased effect of radafaxine on pain and fatigue.[6]

Radafaxine has about 70% of bupropion's efficiacy in blocking dopamine reuptake, and 392% of efficiacy in blocking norepinephrine reuptake.[7] [8]

At least one study suggests that radafaxine has a low abuse potential similar to bupropion.[9]

[edit] References

  1. ^ Restless Legs Syndrome: First Approval
  2. ^ {1} Reviews Novel Therapeutics For CNS Disorders And Confirms Strong Pipeline Momentum - News, Search Jobs, Events
  3. ^ GSK breakthrough on bird flu vaccine - Business News, Business - Independent.co.uk
  4. ^ MeSH radafaxine
  5. ^ GlaxoSmithKline Reviews Novel Therapeutics for CNS Disorders and Confirms Strong Pipeline Momentum
  6. ^ Microsoft PowerPoint - slides_05_burch.ppt
  7. ^ ^ 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.
  8. ^ ^ 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.
  9. ^ Radafaxine
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