Elzasonan

Last updated
Elzasonan
Elzasonan structure.svg
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 4-(3,4-dichlorophenyl)-2-[2-(4-methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C22H23Cl2N3OS
Molar mass 448.41 g·mol−1
3D model (JSmol)
  • Clc4c(Cl)cc(N1C(=O)C(\SCC1)=C\c3ccccc3N2CCN(C)CC2)cc4
  • InChI=1S/C22H23Cl2N3OS/c1-25-8-10-26(11-9-25)20-5-3-2-4-16(20)14-21-22(28)27(12-13-29-21)17-6-7-18(23)19(24)15-17/h2-7,14-15H,8-13H2,1H3/b21-14-
  • Key:LHYMPSWMHXUWSK-STZFKDTASA-N
   (verify)

Elzasonan (CP-448,187) is a selective 5-HT1B and 5-HT1D receptor antagonist that was under development by Pfizer for the treatment of depression but was discontinued, possibly due to poor efficacy. [1] [2] [3] [4] [5] By preferentially blocking 5-HT1B and 5-HT1D autoreceptors, elzasonan is thought to enhance serotonergic innervations originating from the raphe nucleus, thereby improving signaling to limbic regions like the hippocampus and prefrontal cortex and ultimately resulting in antidepressant effects. [3]

Contents

Synthesis

Patent: Elzasonan synthesis.svg
Patent:

The aldol condensation of 2-(4-Methylpiperazino)benzaldehyde [85803-62-9] (1) with 4-(3,4-dichlorophenyl)thiomorpholin-3-one [205683-35-8] (2) gives Elzasonsan (3).

See also

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References

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