Lubazodone

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]

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 Y
PubChem CID	157919
ChemSpider	138947 N
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 N Key:HTODIQZHVCHVGM-JTQLQIEISA-N N
NY (what is this?)  (verify)