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
Classification Click here for help
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2009) in combination with lumefantrine)
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names Click here for help
INN number INN
6458 artemether
Synonyms Click here for help
β-artemether | beta-artemether
Database Links Click here for help
CAS Registry No. 71963-77-4 (source: Scifinder)
ChEBI CHEBI:195280
ChEMBL Ligand CHEMBL566534
DrugBank Ligand DB06697
DrugCentral Ligand 245
GtoPdb PubChem SID 374883842
PubChem CID 68911
RCSB PDB Ligand D8Z
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Wikipedia Artemether

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Tocris
Artemether
Cat. No. 6818