lubazodone

{{Short description|Abandoned experimental antidepressant drug}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 444697864

| IUPAC_name = (2S)-2-[(7-fluoro-2,3-dihydro-1H-inden-4-yl)oxymethyl]morpholine

| image = Lubazodone.svg

| width = 250px

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 161178-07-0

| ATC_prefix = None

| ATC_suffix =

| PubChem = 157919

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 850TB2B172

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 138947

| synonyms = YM-992; YM-35995

| C=14 | H=18 | F=1 | N=1 | O=2

| SMILES = C1CC2=C(C=CC(=C2C1)F)OC[C@@H]3CNCCO3

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HTODIQZHVCHVGM-JTQLQIEISA-N

}}

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.{{cite journal | vauthors = Moltzen EK, Bang-Andersen B | title = Serotonin reuptake inhibitors: the corner stone in treatment of depression for half a century--a medicinal chemistry survey | journal = Current Topics in Medicinal Chemistry | volume = 6 | issue = 17 | pages = 1801–1823 | year = 2006 | pmid = 17017959 | doi = 10.2174/156802606778249810 }}{{cite book| vauthors = Gallagher PT | chapter = Beyond SSRIs: Second-generation Reuptake Inhibitors for the Treatment of Depression | veditors = Rankovic Z, Hargreaves R, Bingham M |title=Drug Discovery for Psychiatric Disorders| chapter-url = https://books.google.com/books?id=e3YoDwAAQBAJ&pg=PA193|date=8 October 2012|publisher=Royal Society of Chemistry|isbn=978-1-84973-494-3|pages=193–}}{{Cite web|url=http://adisinsight.springer.com/drugs/800008166|title = Lubazodone | work = AdisInsight | publisher = Springer Nature Switzerland AG }} It acts as a serotonin reuptake inhibitor (K_i for {{abbrlink|SERT|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). 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). 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. It reached phase II clinical trials for depression, but development was discontinued in 2001 reportedly due to the "erosion of the {{abbrlink|SSRI|selective serotonin reuptake inhibitor}} market in the United States".