Litoxetine

Litoxetine
Clinical data
Other names	SL 81-0385; IXA-001
ATC code	None;
Identifiers
	IUPAC name 4-(naphthalen-2-ylmethoxy)piperidine;
CAS Number	86811-09-8;
PubChem CID	65650;
ChemSpider	59087;
UNII	9980ST005G;
ChEMBL	ChEMBL471036;
CompTox Dashboard (EPA)	DTXSID30235828 ;
Chemical and physical data
Formula	C16H19NO
Molar mass	241.334 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3CNCCC3OCc2cc1ccccc1cc2;

Litoxetine (developmental code names SL 81-0385, IXA-001) is an antidepressant which was under clinical development for the treatment of depression in the early 1990s but was never marketed.^[1]^[2] It acts as a potent serotonin reuptake inhibitor (K_i for SERTTooltip serotonin transporter = 7 nM) and modest 5-HT₃ receptor antagonist (K_i = 315 nM).^[3]^[4] It has antiemetic activity, and unlike the selective serotonin reuptake inhibitors (SSRIs), appears to have a negligible incidence of nausea and vomiting.^[5] The drug is structurally related to indalpine.^[4] Development of litoxetine for depression was apparently ceased in the late 1990s.^[1] However, as of March 2017, development of litoxetine has been reinitiated and the drug is now in the phase II stage for the treatment of urinary incontinence.^[1]

References

^ ^a ^b ^c "Litoxetine - IXALTIS". AdisInsight. Springer Nature Switzerland AG. Retrieved 2018-08-25.
^ Fairweather DB, Patat A, Rosenzweig P, Curson VH, Dunmore C, Dubruc C, Hindmarch I (August 1995). "The psychomotor and cognitive effects of litoxetine in young and middle aged volunteers". British Journal of Clinical Pharmacology. 40 (2): 119–125. doi:10.1111/j.1365-2125.1995.tb05767.x. PMC 1365170. PMID 8562293.
^ Gallagher PT (8 October 2012). "Beyond SSRIs: Second-generation Reuptake Inhibitors for the Treatment of Depression". In Rankovic Z, Hargreaves R, Bingham M (eds.). Drug Discovery for Psychiatric Disorders. Royal Society of Chemistry. pp. 195–. ISBN 978-1-84973-494-3.
^ ^a ^b Olivier B, Soudijn W, van Wijngaarden I (6 December 2012). "Serotonin, dopamine, and norepinephrine transporters". In Jucker E (ed.). Progress in Drug Research. Birkhäuser. pp. 80–. ISBN 978-3-0348-8391-7.
^ Angel I, Schoemaker H, Prouteau M, Garreau M, Langer SZ (March 1993). "Litoxetine: a selective 5-HT uptake inhibitor with concomitant 5-HT3 receptor antagonist and antiemetic properties". European Journal of Pharmacology. 232 (2–3): 139–145. doi:10.1016/0014-2999(93)90767-C. PMID 8385615.