lanicemine   Click here for help

GtoPdb Ligand ID: 7681

Synonyms: AR-R15896AR | ARL 15896 | AZD-6765 | AZD6765
Compound class: Synthetic organic
Comment: Lanicemine (AZD 6765) was originally developed as a neuroprotective agent, but was repurposed as an antidepressant with potential for the management of severe and treatment-resistant depression [3]. However, the compound failed to meet study endpoints, so development was halted. The compound is discussed in the AZ 2014 review paper [1].
The structure represented here shows stereochemistry identical to the INN record wheras PubChem CID 3038485 represents the non-chiral molecule.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 38.91
Molecular weight 198.12
XLogP 1.95
No. Lipinski's rules broken 0
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Canonical SMILES NC(c1ccccc1)Cc1ccccn1
Isomeric SMILES N[C@H](c1ccccc1)Cc1ccccn1
InChI InChI=1S/C13H14N2/c14-13(11-6-2-1-3-7-11)10-12-8-4-5-9-15-12/h1-9,13H,10,14H2/t13-/m0/s1
1. Cook D, Brown D, Alexander R, March R, Morgan P, Satterthwaite G, Pangalos MN. (2014)
Lessons learned from the fate of AstraZeneca's drug pipeline: a five-dimensional framework.
Nat Rev Drug Discov, 13 (6): 419-31. [PMID:24833294]
2. Monaghan DT, Larsen H. (1997)
NR1 and NR2 subunit contributions to N-methyl-D-aspartate receptor channel blocker pharmacology.
J Pharmacol Exp Ther, 280 (2): 614-20. [PMID:9023271]
3. Zarate Jr CA, Mathews D, Ibrahim L, Chaves JF, Marquardt C, Ukoh I, Jolkovsky L, Brutsche NE, Smith MA, Luckenbaugh DA. (2013)
A randomized trial of a low-trapping nonselective N-methyl-D-aspartate channel blocker in major depression.
Biol Psychiatry, 74 (4): 257-64. [PMID:23206319]