NS-2359

NS-2359
Clinical data
ATC code	none;
Identifiers
	IUPAC name (1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-(methoxymethyl)-8-azabicyclo[3.2.1]octane;
PubChem CID	11408320;
UNII	76H76554PA;
Chemical and physical data
Formula	C15H19Cl2NO
Molar mass	300.22 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1Cl)C(C2COC)CC3NC2CC3;
	InChI InChI=1S/C15H19Cl2NO/c1-19-8-12-11(7-10-3-5-15(12)18-10)9-2-4-13(16)14(17)6-9/h2,4,6,10-12,15,18H,3,5,7-8H2,1H3/t10-,11+,12+,15+/m0/s1; Key:FPTPUYCHSWIWIB-FUTJPDQTSA-N;
	(verify)

NS-2359 (GSK-372475) is a serotonin-norepinephrine-dopamine reuptake inhibitor. It was under development by GlaxoSmithKline (GSK) as an antidepressant,^[1] but was discontinued in 2009 when phase II clinical trials showed the drug was not effective and not well tolerated.^[2] The results did not support further effort by the company.^[1] NS-2359 was also in clinical trials for the treatment of ADHD,^[3] phase II having been completed in 2007.^[4] A phase I clinical trial exploring the effect of NS-2359 on cocaine-dependent individuals was completed in 2002.^[5]

References

^ ^a ^b "NeuroSearch announces the results of Phase II Proof of Concept studies with NS2359 in depression". NeuroSearch. Archived from the original on 2016-03-04. Retrieved 2009-06-20.
^ Learned S, Graff O, Roychowdhury S, Moate R, Krishnan KR, Archer G, Modell JG, Alexander R, Zamuner S, Lavergne A, Evoniuk G, Ratti E (May 2012). "Efficacy, safety, and tolerability of a triple reuptake inhibitor GSK372475 in the treatment of patients with major depressive disorder: two randomized, placebo- and active-controlled clinical trials". Journal of Psychopharmacology. 26 (5): 653–62. doi:10.1177/0269881111424931. PMID 22048884. S2CID 9365152.
^ Wilens TE, Klint T, Adler L, West S, Wesnes K, Graff O, Mikkelsen B (June 2008). "A randomized controlled trial of a novel mixed monoamine reuptake inhibitor in adults with ADHD". Behavioral and Brain Functions. 4: 24. doi:10.1186/1744-9081-4-24. PMC 2442604. PMID 18554401.
^ Clinical trial number NCT00467428 for "Efficacy and Safety of NS2359 in Adults With Attention Deficit Hyperactivity Disorder" at ClinicalTrials.gov
^ Clinical trial number NCT00032916 for "Interaction Study With NS2359 and Cocaine in Cocaine Experienced Volunteers" at ClinicalTrials.gov

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v t e Phenyltropanes (classifications)
2-Carboxymethyl Esters	Troparil WIN 35428 RTI-31 RTI-32 RTI-51 RTI-55 RTI-83
(3,4-Disubstituted Phenyl)-tropanes	Dichloropane RTI-112 RTI-353
Arylcarboxy	RTI-113 RTI-120
Carboxyalkyl	RTI-121 RTI-150
Acyl	PTT/WF-11 WF-23 PIT/WF-21 WF-33
β,α Stereochemistry	RTI-352 RTI-274
α,β Stereochemistry	Brasofensine Tesofensine NS2359
Heterocycles: 3-Substituted-isoxazol-5-yl	RTI-177 RTI-336 RTI-371
Heterocycles: 3-Substituted-1,2,4-oxadiazole	RTI-126 RTI-371
N-alkyl	FP-β-CPPIT FE-β-CPPIT Altropane Ioflupane (¹²³I)
N-replaced (S,O,C)	Tropoxane
Irreversible	RTI-76
Nortropanes (N-demethylated)	NS2359 (GSK-372,475)

Clinical data

ATC code	none
Identifiers
IUPAC name (1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-(methoxymethyl)-8-azabicyclo[3.2.1]octane
PubChem CID	11408320
UNII	76H76554PA
Chemical and physical data
Formula	C₁₅H₁₉Cl₂NO
Molar mass	300.22 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1Cl)C(C2COC)CC3NC2CC3
InChI InChI=1S/C15H19Cl2NO/c1-19-8-12-11(7-10-3-5-15(12)18-10)9-2-4-13(16)14(17)6-9/h2,4,6,10-12,15,18H,3,5,7-8H2,1H3/t10-,11+,12+,15+/m0/s1 Key:FPTPUYCHSWIWIB-FUTJPDQTSA-N
(verify)