Radafaxine

Radafaxine
Clinical data
Other names	(S,S)-Hydroxybupropion; (2S,3S)-Hydroxybupropion; GW-353,162
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol;
CAS Number	192374-14-4 ; HCl: 106083-71-0 ;
PubChem CID	9795056;
ChemSpider	7970823 ;
UNII	Q47741214K; HCl: SYD411HZ3S ;
ChEMBL	ChEMBL1172928 ;
CompTox Dashboard (EPA)	DTXSID501318447 ;
Chemical and physical data
Formula	C13H18ClNO2
Molar mass	255.74 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:RCOBKSKAZMVBHT-TVQRCGJNSA-N ;
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Radafaxine (developmental code GW-353,162; also known as (2S,3S)-hydroxybupropion or (S,S)-hydroxybupropion^[1]) is a norepinephrine–dopamine reuptake inhibitor (NDRI) which was under development by GlaxoSmithKline in the 2000s for a variety of different indications but was never marketed.^[2] These uses included treatment of restless legs syndrome, major depressive disorder, bipolar disorder, neuropathic pain, fibromyalgia, and obesity.^[2] Regulatory filing was planned for 2007,^[3] but development was discontinued in 2006 due to "poor test results".^[4]

^ Carroll FI, Blough BE, Mascarella SW, Navarro HA, Lukas RJ, Damaj MI (2014). "Bupropion and Bupropion Analogs as Treatments for CNS Disorders". Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Advances in Pharmacology. Vol. 69. pp. 177–216. doi:10.1016/B978-0-12-420118-7.00005-6. ISBN 9780124201187. PMID 24484978.
^ ^a ^b "Radafaxine - AdisInsight".
^ "Reviews Novel Therapeutics For CNS Disorders And Confirms Strong Pipeline Momentum". BioSpace. 23 November 2004. Archived from the original on 2007-09-28.
^ Kollewe J (27 July 2006). "GSK breakthrough on bird flu vaccine". Independent.co.uk. Archived from the original on 2007-10-01.