Radafaxine
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| Systematic (IUPAC) name | |
| (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 106083-71-0  |
| ATC code | None |
| PubChem | CID 9795056 |
| ChemSpider | 7970823  |
| UNII | Q47741214K |
| ChEMBL | CHEMBL1172928 |
| Chemical data | |
| Formula | C13H18ClNO2 |
| Mol. mass | 292.20 g/mol |
| SMILES | eMolecules & PubChem |
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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 |
[edit] Chemistry
It is a potent metabolite of bupropion, the compound in GlaxoSmithKline's Wellbutrin. More specifically, "6-hydroxybupropion" is an analogue of bupropion, and radafaxine is an isolated isomer of 6-hydroxybupropion.[4]
Therefore, radafaxine builds on at least some of the properties of bupropion in humans.[5]
[edit] 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 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 efficacy in blocking dopamine reuptake, and 392% of efficacy in blocking norepinephrine reuptake.[7][8]
At least one study suggests that radafaxine has a low abuse potential similar to bupropion.[9]
[edit] See also
[edit] References
- ^ Restless Legs Syndrome: First Approval
- ^ {1} Reviews Novel Therapeutics For CNS Disorders And Confirms Strong Pipeline Momentum - News, Search Jobs, Events
- ^ "RSPCA backs rabies quarantine move". The Independent (London). 20 September 1998. http://news.independent.co.uk/business/news/article1199374.ece#10919204097707524565.
- ^ MeSH radafaxine
- ^ GlaxoSmithKline Reviews Novel Therapeutics for CNS Disorders and Confirms Strong Pipeline Momentum
- ^ Microsoft PowerPoint - slides_05_burch.ppt
- ^ 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.
- ^ Radafaxine
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