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)
Compound class: Synthetic organic
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.

artemether is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
No information available.
Summary of Clinical Use Click here for help
Artemether is on the World Health Organization's Model List of Essential Medicines. The 2009 US FDA approval for this compound is in combination with lumefantrine (trade name Coartem®) and is one of the artemisinin-based combination therapies (ACTs) recommended in the World Health Organization's Guidelines for the treatment of malaria [4]. The European Medicines Agency (EMA) granted orphan designation for the combined formulation in 2010 (link to the EMA Orphan Designation record here). The WHO guidelines also recommend intramuscular injection of artemether for the treatment of severe malaria if artesunate is not available [3].
The link to extended ADME data provided below is for the combined formulation with lumefantrine.
External links Click here for help
For extended ADME data see the following:

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