artemether   Click here for help

GtoPdb Ligand ID: 9955

Synonyms: β-artemether | beta-artemether
Approved drug PDB Ligand Antimalarial Ligand
artemether is an approved drug (FDA (2009) in combination with lumefantrine)
Comment: Artemether is a semisynthetic derivative of artemisinin, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). Synthesis yields two crystalline anomers, α- and β-artemether, the latter predominates and is marginally more active [2].
Artemether is a prodrug that is converted to the active metabolite artenimol (dihydroartemisinin).

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 5
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 46.15
Molecular weight 298.18
XLogP 3.33
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES CO[C@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
InChI InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1
InChI Key SXYIRMFQILZOAM-HVNFFKDJSA-N
Bioactivity Comments
The interaction table below provides data from an evaluation of the antimalarial (asexual blood stage) activity of artemether, using a panel of P. falciparum strains.
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 - - 8.9 pIC50 - 1
pIC50 8.9 (IC50 1.4x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1 Parasite growth inhibition assay - - 8.7 pIC50 - 1
pIC50 8.7 (IC50 2.2x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfV1/S Parasite growth inhibition assay - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 2.9x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite growth inhibition assay - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.5x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfD6 Parasite growth inhibition assay - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.5x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Parasite growth inhibition assay - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.5x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfTM90C2A Parasite growth inhibition assay - - 8.3 pIC50 - 1
pIC50 8.3 (IC50 5.1x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)