Lubazodone

Lubazodone
Clinical data
Other names	YM-992; YM-35995
Routes of; administration	Oral
ATC code	None;
Identifiers
	IUPAC name (2S)-2-[(7-fluoro-2,3-dihydro-1H-inden-4-yl)oxymethyl]morpholine;
CAS Number	161178-07-0 ;
PubChem CID	157919;
ChemSpider	138947 ;
UNII	850TB2B172;
CompTox Dashboard (EPA)	DTXSID30167074 ;
Chemical and physical data
Formula	C14H18FNO2
Molar mass	251.301 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC2=C(C=CC(=C2C1)F)OC[C@@H]3CNCCO3;
	InChI InChI=1S/C14H18FNO2/c15-13-4-5-14(12-3-1-2-11(12)13)18-9-10-8-16-6-7-17-10/h4-5,10,16H,1-3,6-9H2/t10-/m0/s1 ; Key:HTODIQZHVCHVGM-JTQLQIEISA-N ;
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Lubazodone (developmental code names YM-992, YM-35995) is an experimental antidepressant which was under development by Yamanouchi for the treatment for major depressive disorder in the late 1990s and early 2000s but was never marketed.^[1]^[2]^[3] It acts as a serotonin reuptake inhibitor (K_i for SERTTooltip serotonin transporter = 21 nM) and 5-HT_2A receptor antagonist (K_i = 86 nM), and hence has the profile of a serotonin antagonist and reuptake inhibitor (SARI).^[1]^[2] The drug has good selectivity against a range of other monoamine receptors, with its next highest affinities being for the α₁-adrenergic receptor (K_i = 200 nM) and the 5-HT_2C receptor (K_i = 680 nM).^[1] Lubazodone is structurally related to trazodone and nefazodone, but is a stronger serotonin reuptake inhibitor and weaker as a 5-HT_2A receptor antagonist in comparison to them and is more balanced in its actions as a SARI.^[1]^[2] It reached phase II clinical trials for depression,^[3] but development was discontinued in 2001 reportedly due to the "erosion of the SSRITooltip selective serotonin reuptake inhibitor market in the United States".^[1]

References

^ ^a ^b ^c ^d ^e Moltzen EK, Bang-Andersen B (2006). "Serotonin reuptake inhibitors: the corner stone in treatment of depression for half a century--a medicinal chemistry survey". Current Topics in Medicinal Chemistry. 6 (17): 1801–1823. doi:10.2174/156802606778249810. PMID 17017959.
^ ^a ^b ^c 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. 193–. ISBN 978-1-84973-494-3.
^ ^a ^b "Lubazodone". AdisInsight. Springer Nature Switzerland AG.