Chemistry:Eplivanserin

Short description: 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
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.

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-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.

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

• Pimavanserin
• Volinanserin