Lubazodone

Abandoned experimental antidepressant drug
  • None
Identifiers
  • (2S)-2-[(7-fluoro-2,3-dihydro-1H-inden-4-yl)oxymethyl]morpholine
CAS Number
  • 161178-07-0 checkY
PubChem CID
  • 157919
ChemSpider
  • 138947 ☒N
UNII
  • 850TB2B172
CompTox Dashboard (EPA)
  • DTXSID30167074 Edit this at Wikidata
Chemical and physical dataFormulaC14H18FNO2Molar mass251.301 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

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 (Ki for SERTTooltip serotonin transporter = 21 nM) and 5-HT2A receptor antagonist (Ki = 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 (Ki = 200 nM) and the 5-HT2C receptor (Ki = 680 nM).[1] Lubazodone is structurally related to trazodone and nefazodone, but is a stronger serotonin reuptake inhibitor and weaker as a 5-HT2A 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

  1. ^ 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.
  2. ^ 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.
  3. ^ a b "Lubazodone". AdisInsight. Springer Nature Switzerland AG.

External links

  • Lubazodone - AdisInsight
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transportersOthers
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • See also: Receptor/signaling modulators
  • Adrenergics
  • Dopaminergics
  • Melatonergics
  • Monoamine reuptake inhibitors and releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins
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