Contents

Eplivanserin

Chemical compound

Eplivanserin

Clinical data
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name (Z,E)-1-(2-fluorophenyl)-3-(4-hydroxyphenyl)-2-propen-1-one O-[2-(dimethylamino)ethyl]oxime
CAS Number	130579-75-8 Y 130580-02-8 (fumarate)
PubChem CID	5493160
ChemSpider	13267837 N
UNII	3CO94WO6DJ
KEGG	D10006 N
CompTox Dashboard (EPA)	DTXSID601028413
ECHA InfoCard	100.189.857
Chemical and physical data
Formula	C19H21FN2O2
Molar mass	328.387 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2cc(O)ccc2\C=C\C(=N\OCCN(C)C)\c1ccccc1F
InChI 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
NY (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.^[1]

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.^[2]

Mechanism of action[edit]

Eplivanserin is an inverse agonist on the serotonin receptor subtype 5-HT_2A. In contrast to older sedating drugs acting on 5-HT_2A receptors (e.g., mirtazapine, clozapine, risperidone), eplivanserin has practically no affinity to dopamine, histamine and adrenergic receptors.^[3]

Study results[edit]

In a placebo controlled Phase II clinical trial with 351 subjects, eplivanserin reduced the sleep latency by 39 minutes (versus 26 minutes under placebo).^[3]

Synthesis[edit]

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[edit]

• Pimavanserin
• Volinanserin

References[edit]

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