Amitifadine

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Amitifadine
Clinical data
Pronunciation(/æmɪˈtɪfədiːn/ am-i-TIF-ə-deen)
Other namesDOV-21,947; EB-1010
Legal status
Legal status
Identifiers
  • (1R,5S)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane
JSmol)
  • C1[C@@](CN2)(C1C2)C(=C1)C=C(C(Cl)=C1)Cl
  • InChI=1S/C11H11Cl2N/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11/h1-3,8,14H,4-6H2/t8-,11+/m1/s1 checkY
  • Key:BSMNRYCSBFHEMQ-KCJUWKMLSA-N checkY
  (verify)

Amitifadine (developmental code names DOV-21,947, EB-1010) is a

smoking withdrawal.[1]

Pharmacology

Ki values for SERT, NET, and DAT of amitifadine are 99 nM, 262 nM, and 213 nM.[2] The IC50 values for serotonin, norepinephrine and dopamine uptake are 12, 23 and 96 nM, respectively

Amitifadine and isomers
Compound Uptake (IC50, nM) Binding (Ki, nM)
5-HT NE DA SERT NET DAT
Amitifadine 12 23 96 100 260 210
DOV-216,303 14 20 78 190 380 190
DOV-102,677 130 100 130 740 1000 220

Amitifadine reduces the duration of immobility in the

minimum effective dose (MED) of 5 mg/kg. This antidepressant-like effect manifests in the absence of significant increases in motor activity at doses of up to 20 mg/kg. Amitifadine also produces a dose-dependent reduction in immobility in the tail suspension test, with an oral MED of 5 mg/kg. In microdialysis studies, amitifadine increased extracellular levels of serotonin, norepinephrine and dopamine in brain regions and did not induce hyperactivity in rats.[4]
Results in a small clinical trial indicated that amitifadine had statistically significant antidepressant effects and was well tolerated.[5]

Chemistry

DOV stereochemistry
DOV stereochemistry

Amitifadine is the (+)-enantiomer of DOV-216,303, and its (−)-enantiomer is DOV-102,677.

Amitifadine is very similar in structure to Bicifadine & Centanafadine.

A so-called "bifunctional molecule" from a separate organization called GSK 598809 has related structure.

References

  1. ^ a b c "Amitifadine". AdisInsight. Retrieved 26 February 2017.
  2. ^
    PMID 12586204
    .
  3. ^ a b "Euthymics Reports Top-Line Results From Triade Trial of Amitifadine for Major Depressive Disorder" (PDF). Cambridge, MA: Euthymics Bioscience, Inc. May 29, 2013. Archived from the original (PDF) on 2017-09-24. Retrieved 2017-06-12.
  4. S2CID 32581051
    .
  5. PMID 21925682
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Amitifadine&oldid=1188193637"