dasotraline   Click here for help

GtoPdb Ligand ID: 8308

Synonyms: (1R,4S)-trans-norsertraline | SEP-225,289 | SEP-225289
Compound class: Synthetic organic
Comment: Dasotraline is a triple reuptake inhibitor [1,3]. Such compounds are also known as serotonin-norepinephrine-dopamine reuptake inhibitors, or SNDRIs. Structurally, dasotraline is a stereoisomer of an active metabolite of sertraline, a selective serotonin reuptake inhibitor (SSRI) antidepressant.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 26.02
Molecular weight 291.06
XLogP 4.75
No. Lipinski's rules broken 0
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Canonical SMILES NC1CCC(c2c1cccc2)c1ccc(c(c1)Cl)Cl
Isomeric SMILES N[C@@H]1CC[C@H](c2c1cccc2)c1ccc(c(c1)Cl)Cl
InChI InChI=1S/C16H15Cl2N/c17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13/h1-5,7,9,11,16H,6,8,19H2/t11-,16+/m0/s1
1. Chen Z, Skolnick P. (2007)
Triple uptake inhibitors: therapeutic potential in depression and beyond.
Expert Opin Investig Drugs, 16 (9): 1365-77. [PMID:17714023]
2. DeLorenzo C, Lichenstein S, Schaefer K, Dunn J, Marshall R, Organisak L, Kharidia J, Robertson B, Mann JJ, Parsey RV. (2011)
SEP-225289 serotonin and dopamine transporter occupancy: a PET study.
J Nucl Med, 52 (7): 1150-5. [PMID:21680689]
3. Guiard BP, Chenu F, El Mansari M, Blier P. (2011)
Characterization of the electrophysiological properties of triple reuptake inhibitors on monoaminergic neurons.
Int J Neuropsychopharmacol, 14 (2): 211-23. [PMID:20149268]