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Antidepressant
Lubazodone
Другие языки:

    Lubazodone

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    Lubazodone
    Lubazodone.svg
    Clinical data
    Other names YM-992; YM-35995
    Routes of
    administration    		 Oral
    ATC code
    • None
    Identifiers
    • (2S)-2-[(7-fluoro-2,3-dihydro-1H-inden-4-yl)oxymethyl]morpholine
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C14H18FNO2
    Molar mass 251.301 g·mol−1
    3D model (JSmol)
    • C1CC2=C(C=CC(=C2C1)F)OC[C@@H]3CNCCO3
    • 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. It acts as a serotonin reuptake inhibitor (Ki for SERT = 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 SSRI market in the United States".

    Synthesis

    Patent:

    Thus reaction of 7-fluoro-4-indanol [161178-24-1] (1) with (S)-glycidyl methanesulfonate, CID:12461090 (2) in the presence of base leads to the epoxypropyl ether, CID:139677486 (3). Treatment with aminoethyl sulfate [926-39-6] (4) closes the morpholine ring giving Lubazodone (5).

    External links



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