DOV-216,303

DOV-216,303
Legal status
Legal status	US: Investigational New Drug;
Identifiers
	IUPAC name 1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane;
CAS Number	66504-40-3 ;
PubChem CID	9795276;
ChemSpider	7971043 ;
UNII	5W2YA6F455;
ChEMBL	ChEMBL528995 ;
Chemical and physical data
Formula	C11H11Cl2N
Molar mass	228.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C2C1(CNC2)C3=CC(=C(C=C3)Cl)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 ; Key:BSMNRYCSBFHEMQ-UHFFFAOYSA-N ;
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DOV 216,303 is an experimental antidepressant drug originally developed by DOV Pharmaceutical and was licensed to Merck & Co. in 2004;^[1] Merck and DOV terminated their relationship in December 2006.^[2]^: 12^[3]

It is a triple reuptake inhibitor (TRI), or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).^[4] It is the racemic mixture of amitifadine (DOV-21,947) and its (–)-enantiomer, DOV-102,677. Its IC₅₀ values for SERT, NET, and DAT are K_i 14 nM, 20 nM, and 78 nM, respectively.^[4]

As of March 2008, DOV had no intention to further develop DOV-216,303 because the patent on the compound had expired.^[2]^: 6

In a mouse model, DOV-216,303 has shown the ability to promote recovery after spinal cord contusion.^[5]

References

^ McCoy M (August 12, 2004). "Merck and DOV Pharmaceutical In Drug Pact". Chemical & Engineering News.
^ ^a ^b "10-K For the fiscal year ended December 31, 2007". Dov Pharmaceutical via SEC Edgar. March 31, 2008. DOV 216,303 was originally in development for depression; however as the patented composition of matter claim has expired, there are no ongoing clinical trials of DOV 216,303 and none are planned.
^ "DOV 216303". Adis Insight. Springer Nature Switzerland AG. Retrieved 26 February 2017.
^ ^a ^b Skolnick P, Krieter P, Tizzano J, Basile A, Popik P, Czobor P, Lippa A (2006). "Preclinical and clinical pharmacology of DOV 216,303, a "triple" reuptake inhibitor". CNS Drug Reviews. 12 (2): 123–34. doi:10.1111/j.1527-3458.2006.00123.x. PMC 6494125. PMID 16958986.
^ Chu TH, Cummins K, Stys PK (May 2018). "The triple monoamine re-uptake inhibitor DOV 216,303 promotes functional recovery after spinal cord contusion injury in mice". Neuroscience Letters. 675: 1–6. doi:10.1016/j.neulet.2018.03.050. PMID 29578004. S2CID 5007186.