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A9361

Sigma-Aldrich

Artemether

≥98% (HPLC)

Synonym(s):

Dihydroartemisinin methyl ether, Dihydroqinghaosu methyl ether, SM-224

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About This Item

Empirical Formula (Hill Notation):
C16H26O5
CAS Number:
71963-77-4
Molecular Weight:
298.37
MDL number:
MFCD00866205
UNSPSC Code:
51101908
PubChem Substance ID:
329771050
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +155 to +175°, c = 0.5 in methanol

color

off-white to light brown

solubility

DMSO: ≥20 mg/mL

originator

Novartis

storage temp.

room temp

SMILES string

CO[C@H]1OC2O[C@@]3(C)CCC4[C@H](C)CCC([C@H]1C)[C@@]24OO3

InChI

1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1

InChI key

SXYIRMFQILZOAM-HVNFFKDJSA-N

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General description

Artemisinin (ART) is a natural compound present in Artemisia annua, a traditional Chinese plant.

Application

Artemether has been used:
  • as an anti-schistosomal compound to test it effect on the larval stages of S. mansoni
  • to sensitize mouse embryonic fibroblasts (MEFs) and human osteosarcoma HT1080 cells to cysteine starvation (STV)-induced ferroptosis
  • to stimulate islets and its effect on α to β transdifferentiation

Biochem/physiol Actions

Artemether is a methyl ether derivative of artemisinin. It is used against multi-drug resistant strains of the malaria parasite, Plasmodium falciparum, and shows potential in treatment of schistosomiasis.
Artemisinin possesses a highly reactive endoperoxide bridge, which is core for its therapeutic potential. The endoperoxide bond reacts with iron in the erythrocytes with malarial parasite. This leads to the generation of reactive oxygen species (ROS) directly targeting the parasite. Artemisinin also regulates ferroptosis in tumor cells. The α cell transcription factor Arx expression is reduced by artemether. Prolonged exposure of primary islets also resulted in loss if identity in endocrine cell types and their functionality.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H242,H302

Hazard Classifications

Acute Tox. 4 Oral - Org. Perox. D

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dylan R Pillai et al.
Malaria journal, 11, 131-131 (2012-05-01)
Monitoring resistance phenotypes for Plasmodium falciparum, using in vitro growth assays, and relating findings to parasite genotype has proved particularly challenging for the study of resistance to artemisinins. Plasmodium falciparum isolates cultured from 28 returning travellers diagnosed with malaria were
Urs Duthaler et al.
Veterinary parasitology, 186(3-4), 270-280 (2011-12-31)
The pharmacokinetic (PK) parameters of artesunate, artemether and their metabolites dihydroartemisinin (DHA) and dihydroartemisinin-glucuronide (DHA-glucuronide) were determined in sheep naturally infected with Fasciola hepatica. Sheep were treated either with artesunate (intramuscular (i.m.): 40 and 60 mg/kg) or artemether (i.m.: 40
Talitha van der Meulen et al.
Cell metabolism, 27(1), 218-225 (2017-11-07)
Pancreatic α cells retain considerable plasticity and can, under the right circumstances, transdifferentiate into functionally mature β cells. In search of a targetable mechanistic basis, a recent paper suggested that the widely used anti-malaria drug artemether suppresses the α cell
Bart M J De Spiegeleer et al.
Journal of pharmaceutical and biomedical analysis, 70, 111-116 (2012-07-10)
During the stability evaluation of β-artemether containing finished drug products, a consistent and disproportional increase in the UV-peak areas of β-artemether degradation products, when compared to the peak area decline of β-artemether itself, was observed. This suggested that the response
Karina Knudsmark Jessing et al.
Journal of agricultural and food chemistry, 59(21), 11735-11743 (2011-10-04)
The area cultivated with Artemisia annua for the extraction of the antimalarial compound artemisinin is increasing, but the environmental impact of this cultivation has not yet been studied. A sensitive and robust method using liquid chromatography-tandem mass spectrometry (LC-MS/MS) was
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