Amitifadine

Amitifadine

Systematic (IUPAC) name
(1R,5S)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane
Clinical data
Legal status	Investigational New Drug
Identifiers
CAS Number	410074-73-6
PubChem	CID: 11658655
ChemSpider	9833390 Y
KEGG	D10088 Y
ChEMBL	CHEMBL592374 Y
Chemical data
Formula	C11H11Cl2N
Molecular mass	228.118 g/mol
SMILES C1[C@@](CN2)(C1C2)C(=C1)C=C(C(Cl)=C1)Cl
InChI 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 Y Key:BSMNRYCSBFHEMQ-KCJUWKMLSA-N Y
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Amitifadine (am-i-TIF-a-deen), also known as DOV-21,947 or EB-1010, is an antidepressant drug being developed by Euthymics Bioscience Inc. It is a so-called triple reuptake inhibitor (TRI) or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).

It is the (+)-enantiomer of DOV-216,303, and its (−)-enantiomer is DOV-102,677. K_i values for SERT, NET, and DAT are 99 nM, 262 nM, and 213 nM. The IC₅₀ values for serotonin, norepinephrine and dopamine uptake are 12, 23 and 96 nM, respectively

DOV stereochemistry

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

Amitifadine reduces the duration of immobility in the forced swim test in rats with an oral 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. Results in a small clinical trial indicated that amitifadine had statistically significant antidepressant effects and was well tolerated.

See also

• Bicifadine
• GSK1360707F

External links

• Amifitadine Euthymics Bioscience