GSK1521498   Click here for help

GtoPdb Ligand ID: 9287

Synonyms: GSK-1521498
Compound class: Synthetic organic
Comment: GSK1521498 is a μ opioid receptor antagonist [4-5] in clinical development for disorders of compulsive consumption (e.g stimulant drug seeking, binge eating [7], or excessive alcohol consumption). It is >10-fold selective for human μ receptor compared to the κ and δ receptors in vitro [4]. It may be used experimentally as the phosphate with IUPAC name N-{[3,5-difluoro-3′-(1H-1,2,4-triazol-3-yl)-4-biphenylyl]methyl}-2,3-dihydro-1H-inden-2-amine phosphate (1:1). The chemical structure of GSK1521498 is claimed in patent US8822518 [2], with prior chemical series claimed in WO2008021849 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 53.6
Molecular weight 402.17
XLogP 5.41
No. Lipinski's rules broken 1
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Canonical SMILES Fc1cc(cc(c1CNC1Cc2c(C1)cccc2)F)c1cccc(c1)c1ncn[nH]1
Isomeric SMILES Fc1cc(cc(c1CNC1Cc2c(C1)cccc2)F)c1cccc(c1)c1ncn[nH]1
InChI InChI=1S/C24H20F2N4/c25-22-11-19(15-6-3-7-18(8-15)24-28-14-29-30-24)12-23(26)21(22)13-27-20-9-16-4-1-2-5-17(16)10-20/h1-8,11-12,14,20,27H,9-10,13H2,(H,28,29,30)
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Molecular structure representations generated using Open Babel