{{Short description|Abandoned experimental antidepressant drug}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 444697864 | IUPAC_name = (2''S'')-2-[(7-fluoro-2,3-dihydro-1''H''-inden-4-yl)oxymethyl]morpholine | image = Lubazodone.svg | image_class = skin-invert-image | width = 250px

<!--Clinical data--> | tradename = | pregnancy_category = | legal_status = | routes_of_administration = Oral | class = Serotonin antagonist and reuptake inhibitor (SARI); Serotonin reuptake inhibitor; Serotonin 5-HT<sub>2A</sub> receptor antagonist

<!--Pharmacokinetic data--> | bioavailability = | metabolism = | elimination_half-life = | excretion =

<!--Identifiers--> | 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

<!--Chemical data--> | 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.<ref name="pmid17017959">{{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 }}</ref><ref name="RankovicHargreaves2012">{{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–}}</ref><ref name="AdisInsight">{{Cite web|url=http://adisinsight.springer.com/drugs/800008166|title = Lubazodone | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref> It acts as a serotonin reuptake inhibitor (K<sub>i</sub> for {{abbrlink|SERT|serotonin transporter}} = 21&nbsp;nM) and 5-HT<sub>2A</sub> receptor antagonist (K<sub>i</sub> = 86&nbsp;nM), and hence has the profile of a serotonin antagonist and reuptake inhibitor (SARI).<ref name="pmid17017959" /><ref name="RankovicHargreaves2012" /> The drug has good selectivity against a range of other monoamine receptors, with its next highest affinities being for the α<sub>1</sub>-adrenergic receptor (K<sub>i</sub> = 200&nbsp;nM) and the 5-HT<sub>2C</sub> receptor (K<sub>i</sub> = 680&nbsp;nM).<ref name="pmid17017959" /> Lubazodone is structurally related to trazodone and nefazodone, but is a stronger serotonin reuptake inhibitor and weaker as a 5-HT<sub>2A</sub> receptor antagonist in comparison to them and is more balanced in its actions as a SARI.<ref name="pmid17017959" /><ref name="RankovicHargreaves2012" /> It reached phase II clinical trials for depression,<ref name="AdisInsight" /> but development was discontinued in 2001 reportedly due to the "erosion of the {{abbrlink|SSRI|selective serotonin reuptake inhibitor}} market in the United States".<ref name="pmid17017959" />

== References == {{Reflist|2}}

== External links == * [http://adisinsight.springer.com/drugs/800008166 Lubazodone - AdisInsight]

{{Monoamine reuptake inhibitors}} {{Serotonin receptor modulators}}

Category:5-HT2A antagonists Category:Alpha-1 blockers Category:Antidepressants Category:Indanes Category:Morpholines Category:Organofluorides Category:Phenol ethers Category:Serotonin reuptake inhibitors Category:Abandoned drugs

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