Structure via PubChem · Public domain (PubChem)
lubazodone
Sign in to saveLubazodone (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. It acts as a serotonin reuptake inhibitor (Ki for = 21 nM) and 5-HT2A receptor antagonist (Ki = 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 (Ki = 200 nM) a
Chemical data
- Formula
- C14H18FNO2
- Molecular weight
- 251.3 g/mol
- IUPAC name
- (2S)-2-[(7-fluoro-2,3-dihydro-1H-inden-4-yl)oxymethyl]morpholine
- SMILES
- C1CC2=C(C=CC(=C2C1)F)OC[C@@H]3CNCCO3
- InChIKey
- HTODIQZHVCHVGM-JTQLQIEISA-N
- XLogP
- 2.1
- Polar surface area
- 30.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 251.132
Show 4 more facts
- chemical formula
- C₁₄H₁₈FNO₂
- canonical SMILES
- C1CC2=C(C=CC(=C2C1)F)OCC3CNCCO3
- isomeric SMILES
- C1CC2=C(C=CC(=C2C1)F)OC[C@@H]3CNCCO3
- Commons category
- Lubazodone
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
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. It acts as a serotonin reuptake inhibitor (Ki for = 21 nM) and 5-HT2A receptor antagonist (Ki = 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 (Ki = 200 nM) and the 5-HT2C receptor (Ki = 680 nM). 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. It reached phase II clinical trials for depression, but development was discontinued in 2001 reportedly due to the "erosion of the market in the United States".
== References ==
Excerpted from Wikipedia’s “lubazodone” article, available under the CC BY-SA 4.0 licence.