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Hypnotics
Eplivanserin
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    Eplivanserin

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    Eplivanserin
    Eplivanserin structure.svg
    Clinical data
    Routes of
    administration    		 Oral
    ATC code
    • none
    Identifiers
    • (Z,E)-1-(2-fluorophenyl)-3-(4-hydroxyphenyl)-2-propen-1-one O-[2-(dimethylamino)ethyl]oxime
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ECHA InfoCard 100.189.857
    Chemical and physical data
    Formula C19H21FN2O2
    Molar mass 328.387 g·mol−1
    3D model (JSmol)
    • c2cc(O)ccc2\C=C\C(=N\OCCN(C)C)\c1ccccc1F
    • InChI=1S/C19H21FN2O2/c1-22(2)13-14-24-21-19(17-5-3-4-6-18(17)20)12-9-15-7-10-16(23)11-8-15/h3-12,23H,13-14H2,1-2H3/b12-9+,21-19- ☒N
    • Key:VAIOZOCLKVMIMN-PRJWTAEASA-N ☒N
     ☒NcheckY (what is this?)  (verify)

    Eplivanserin (SR-46,349; planned trade name Ciltyri) was an experimental drug for the treatment of insomnia which was being developed by Sanofi Aventis.

    Sanofi Aventis announced in December 2009 that it was withdrawing its application for approval of eplivanserin from both the U.S. Food and Drug Administration and the European Medicines Agency.

    Mechanism of action

    Eplivanserin is an inverse agonist on the serotonin receptor subtype 5-HT2A. In contrast to older sedating drugs acting on 5-HT2A receptors (e.g., mirtazapine, clozapine, risperidone), eplivanserin has practically no affinity to dopamine, histamine and adrenergic receptors.

    Study results

    In a placebo controlled Phase II clinical trial with 351 subjects, eplivanserin reduced the sleep latency by 39 minutes (versus 26 minutes under placebo).

    Synthesis

    Patent:Chinese

    The condensation between 2'-Fluoroacetophenone [445-27-2] (5) & 4-hydroxybenzaldehyde [123-08-0] (6) give a chalcone intermediate (also an enone), i.e. CID:53982926 (7).

    (2-chloroethyl)dimethylamine (CDMA) & acetone oxime are reacted together to give dimethylaminoacetoxime (DMA acetoxime), CID:16641114 (3).

    Convergent synthesis gives the product as a mixture of isomers.

    See also


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