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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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J Utzinger et al.
Current medicinal chemistry, 8(15), 1841-1860 (2002-01-05)
Human schistosomiasis, a chronic and debilitating parasitic disease of the tropics, is ranked second after malaria in terms of public health importance. At present, there is no vaccine available, and chemotherapy is the cornerstone of schistosomiasis control. Praziquantel is the
Sören Frahm et al.
PLoS neglected tropical diseases, 13(1), e0006590-e0006590 (2019-01-29)
The arsenal in anthelminthic treatment against schistosomiasis is limited and relies almost exclusively on a single drug, praziquantel (PZQ). Thus, resistance to PZQ could constitute a major threat. Even though PZQ is potent in killing adult worms, its activity against
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
André Lin Ouédraogo et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 60(3), 357-365 (2014-11-22)
Artemisinin combination therapy effectively clears asexual malaria parasites and immature gametocytes but does not prevent posttreatment malaria transmission. Ivermectin (IVM) may reduce malaria transmission by killing mosquitoes that take blood meals from IVM-treated humans. In this double-blind, placebo-controlled trial, 120
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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