API reference

Artesunate

CAS number
88495-63-0
Molecular formula
C19H28O8
Molecular weight
384.4 g/mol
Artesunate — 2D structure
2D structure (PubChem)

About this molecule

Artesunate is a water-soluble, semi-synthetic derivative of the sesquiterpine lactone artemisinin with anti-malarial, anti-schistosomiasis, antiviral, and potential anti-neoplastic activities. Upon hydrolysis of artesunate's active endoperoxide bridge moiety by liberated heme in parasite-infected red blood cells, reactive oxygen species and carbon-centered radicals form, which have been shown to damage and kill parasitic organisms. Additionally, in vitro studies demonstrate that this agent induces DNA breakage in a dose-dependent manner. Artesunate has also been shown to stimulate cell differentiation, arrest the cell cycle in the G1 and G2/M phases, inhibit cell proliferation, and induce apoptosis through mitochondrial and caspase signaling pathways. Artemisinin is isolated from the plant Artemisia annua.

Source: NCI Thesaurus (NCIt), via PubChem.

Identifiers

IUPAC name
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
InChIKey
FIHJKUPKCHIPAT-AHIGJZGOSA-N
SMILES
C[C@@H]1CC[C@H]2[C@H]([C@@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC(=O)CCC(=O)O)C
PubChem CID
6917864

Also known as

Artesunate · Artesunic acid · Arsumax · Plasmotrin · Qinghaozhi · Saphnate · Artesunato · Artesunatum

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