artesunate   Click here for help

GtoPdb Ligand ID: 9956

Approved drug PDB Ligand Antimalarial Ligand
artesunate is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Artesunate is a semisynthetic derivative of artemisinin, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). It contains an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of artemisinin and its derivatives.
Artesunate 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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

artesunate 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 8
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 100.52
Molecular weight 384.18
XLogP 2.92
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 OC(=O)CCC(=O)OC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES OC(=O)CCC(=O)O[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/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
InChI Key FIHJKUPKCHIPAT-AHIGJZGOSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2020), EMA (2021))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid
International Nonproprietary Names Click here for help
INN number INN
6459 artesunate
Database Links Click here for help
CAS Registry No. 88495-63-0 (source: Scifinder)
ChEMBL Ligand CHEMBL361497
DrugCentral Ligand 247
GtoPdb PubChem SID 374883843
PubChem CID 6917864
RCSB PDB Ligand D95
Search Google for chemical match using the InChIKey FIHJKUPKCHIPAT-AHIGJZGOSA-N
Search Google for chemicals with the same backbone FIHJKUPKCHIPAT
Search PubMed clinical trials artesunate
Search PubMed titles artesunate
Search PubMed titles/abstracts artesunate
UniChem Compound Search for chemical match using the InChIKey FIHJKUPKCHIPAT-AHIGJZGOSA-N
UniChem Connectivity Search for chemical match using the InChIKey FIHJKUPKCHIPAT-AHIGJZGOSA-N

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Tocris
Artesunate (links to external site)
Cat. No. 6827