.BETA.-ARTESUNATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H28O8
Molecular Weight	384.4208
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](OC(=O)CCC(O)=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4

InChI

InChIKey=FIHJKUPKCHIPAT-NKHDUEHSSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H28O8
Molecular Weight	384.4208
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.google.com/patents/WO2003048167A1
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26615886 | https://www.google.com/patents/WO2013177420A3

.BETA.-ARTESUNATE is enantiomer of artesunate -- a medication used to treat malaria. β-ARTESUNATE is a prodrug that is rapidly converted to its active form dihydroartemisinin. This process involves hydrolysis of the 4-carbon ester group via plasma esterase enzyme. It is hypothesized that the cleavage of endoperoxide bridge in the pharmacophore of DHA generates reactive oxygen species (ROS), which increases oxidative stress and causes malarial protein damage via alkylation. .BETA.-ARTESUNATE have potential application as anticancer agent.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Artesunate and dihydroartemisinin (DHA): unusual decomposition products formed under mild conditions and comments on the fitness of DHA as an antimalarial drug.	2007-10	17694524

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The in vitro cytotoxic activity of the compound 1 (BETA.-ARTESUNATE) was evaluated against sensitive human cancer cells (human hepatoma HepG2 cells, human lung adenocarcinoma A549 cells, human cervical carcinoma HeLa cells and human leukemic K562 cells), multidrug-resistant K562/ADR leukemia cells and human umbilical vein endothelial cells (HUVEC) by CCK-8 assay (drug exposure was for 72 h).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:33:26 GMT 2025` Edited by `admin` on `Mon Mar 31 23:33:26 GMT 2025`
Record UNII	USD5X0Z99I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

.BETA.-ARTESUNATE

Common Name

English

.BETA.-ARTESUNATE, (+)-

Preferred Name

English

ARTESUNATE, .BETA.-

Common Name

English

BUTANEDIOIC ACID, 1-((3R,5AS,6R,8AS,9R,10R,12R,12AR)-DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER

Common Name

English

NSC-759817

Code

English

Code System Code Type Description

NSC

759817