CHEBI:63918 - artesunate

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ChEBI Name artesunate
ChEBI ID CHEBI:63918
Definition An artemisinin derivative that is the hemisuccinate ester of the lactol resulting from the reduction of the lactone carbonyl group of artemisinin. It is used, generally as the sodium salt, for the treatment of malaria.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H28O8
Net Charge 0
Average Mass 384.425
Monoisotopic Mass 384.17842
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
InChIKey FIHJKUPKCHIPAT-AHIGJZGOSA-N
SMILES [H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O4
Roles Classification
Chemical Role(s): oxidising agent
A substance that removes electrons from another reactant in a redox reaction.
(via peroxides )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ferroptosis inducer
Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing artesunate (CHEBI:63918) has role antimalarial (CHEBI:38068)
artesunate (CHEBI:63918) has role antineoplastic agent (CHEBI:35610)
artesunate (CHEBI:63918) has role ferroptosis inducer (CHEBI:173085)
artesunate (CHEBI:63918) is a artemisinin derivative (CHEBI:63920)
artesunate (CHEBI:63918) is a cyclic acetal (CHEBI:59770)
artesunate (CHEBI:63918) is a dicarboxylic acid monoester (CHEBI:36244)
artesunate (CHEBI:63918) is a hemisuccinate (CHEBI:138979)
artesunate (CHEBI:63918) is a semisynthetic derivative (CHEBI:72588)
artesunate (CHEBI:63918) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
4-oxo-4-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-yl]oxy}butanoic acid
INNs Sources
artesunate ChemIDplus
artesunato ChemIDplus
artesunatum ChemIDplus
Synonyms Sources
artesunic acid ChemIDplus
AS ChEBI
butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester NIST Chemistry WebBook
dihydroqinghasu hemsuccinate ChemIDplus
Manual Xrefs Databases
247 DrugCentral
5293084 ChemSpider
Artesunate Wikipedia
D02482 KEGG DRUG
D95 PDBeChem
DB09274 DrugBank
HMDB0240267 HMDB
View more database links
Registry Numbers Types Sources
182824-33-5 CAS Registry Number ChemIDplus
6003212 Reaxys Registry Number Reaxys
88495-63-0 CAS Registry Number NIST Chemistry WebBook
88495-63-0 CAS Registry Number ChemIDplus
88495-63-0 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
26097885 PubMed citation Europe PMC
30704910 PubMed citation Europe PMC
33652561 PubMed citation Europe PMC
33792170 PubMed citation Europe PMC
33814617 PubMed citation Europe PMC
33920029 PubMed citation Europe PMC
Last Modified
07 June 2021