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CHEBI:63918 - artesunate

Default Structure
ChEBI IDCHEBI:63918
ChEBI Nameartesunate
Stars
DefinitionAn 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.
Last Modified7 June 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H28O8
Net Charge0
Average Mass384.425
Monoisotopic Mass384.17842
SMILES[H][C@]12O[C@@H](OC(=O)CCC(=O)O)[C@H](C)[C@]3([H])CC[C@@H](C)[C@]4([H])CC[C@@](C)(OO[C@]143)O2
InChIInChI=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
InChIKeyFIHJKUPKCHIPAT-AHIGJZGOSA-N
Wikipedia
Roles Classification
Chemical Roles:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
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.
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.
Applications:
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.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
antifibrotic agent  Any agent which acts to reduce fibrosis.
ChEBI Ontology
Outgoing Relation(s)
artesunate (CHEBI:63918) has role antifibrotic agent (CHEBI:233423)
artesunate (CHEBI:63918) has role antimalarial (CHEBI:38068)
artesunate (CHEBI:63918) has role antineoplastic agent (CHEBI:35610)
artesunate (CHEBI:63918) has role antiviral agent (CHEBI:22587)
artesunate (CHEBI:63918) has role ferroptosis inducer (CHEBI:173085)
artesunate (CHEBI:63918) has role ophthalmology drug (CHEBI:66981)
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  Source
artesunateChemIDplus
artesunatoChemIDplus
artesunatumChemIDplus
Synonyms  Source
.alpha.-artesunic acidChEMBL
artesunic acidChemIDplus
ASChEBI
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] esterNIST Chemistry WebBook
Dihydroqinghaosu hemisuccinateChEMBL
dihydroqinghasu hemsuccinateChemIDplus
Brand Name  Source
Artesunate amivasChEMBL
Manual XrefsDatabases
247DrugCentral
5293084ChemSpider
ArtesunateWikipedia
D02482KEGG DRUG
D95PDBeChem
DB09274DrugBank
HMDB0240267HMDB
Registry NumbersSources
Reaxys:6003212Reaxys
CAS:182824-33-5ChemIDplus
CAS:88495-63-0KEGG DRUG
CAS:88495-63-0NIST Chemistry WebBook
CAS:88495-63-0ChemIDplus
Citations