GSK369796   Click here for help

GtoPdb Ligand ID: 10411

Synonyms: N-tert-Butyl isoquine
Antimalarial Ligand
Compound class: Synthetic organic
Comment: GSK369796 is a 4-aminoquinoline antimalarial compound that was synthesised using amodiaquine as the template molecule [3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 57.18
Molecular weight 355.15
XLogP 4.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)O)CNC(C)(C)C
Isomeric SMILES Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)O)CNC(C)(C)C
InChI InChI=1S/C20H22ClN3O/c1-20(2,3)23-12-13-4-6-15(11-19(13)25)24-17-8-9-22-18-10-14(21)5-7-16(17)18/h4-11,23,25H,12H2,1-3H3,(H,22,24)
InChI Key ZVMMVSSEAMUNGI-UHFFFAOYSA-N
Bioactivity Comments
The interaction table below provides data from whole cell assays and gives the antiparasite activitity of GSK369796 against a number of Plasmodium lifecycle stages. The results include evaluations of asexual blood stage activity using culture-adapted P. falciparum strains, with GSK369796 demonstrating no evidence of reduced potency against drug resistant strains. In addition, GSK369796 demonstrates oral activity equivalent to amodiaquine when tested in a P. berghei ANKA mouse model (ED90 of 4.7 mg/kg) [3].
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA Pf7G8 Parasite growth inhibition assay - - 8.4 pIC50 - 2
pIC50 8.4 (IC50 3.9x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite growth inhibition assay - - 8.3 pIC50 - 2
pIC50 8.3 (IC50 5.4x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfTM90C2A Parasite growth inhibition assay - - 8.2 pIC50 - 2
pIC50 8.2 (IC50 6x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfD6 Parasite growth inhibition assay - - 8.2 pIC50 - 2
pIC50 8.2 (IC50 6.5x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Parasite growth inhibition assay - - 8.0 pIC50 - 2
pIC50 8.0 (IC50 1.01x10-8 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Parasite growth inhibition assay - - 7.9 pIC50 - 3
pIC50 7.9 (IC50 1.12x10-8 M) [3H]-hypoxanthine incorporation [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfHB3 Parasite growth inhibition assay - - 7.9 pIC50 - 3
pIC50 7.9 (IC50 1.26x10-8 M) [3H]-hypoxanthine incorporation [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1 Parasite growth inhibition assay - - 7.9 pIC50 - 2-3
pIC50 7.9 (IC50 1.33x10-8 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.9 (IC50 1.32x10-8 M) [3H]-hypoxanthine incorporation [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfV1/S Parasite growth inhibition assay - - 7.8 pIC50 - 2
pIC50 7.8 (IC50 1.6x10-8 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf Parasite exflagellation assay - - - - - 2
Total inhibition of exflagellation following 24hour exposure of mature gametocytes to 10µM GSK369796 [2]
Lifecycle stages: Plasmodium mosquito host stage (gametocyte, gamete, zygote, ookinete, oocyst, sporozoite)