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361593

Artemisinin

Name: Artemisinin
Brand: SIGMA

98%

Synonym(s):

Arteannuin, Qinghaosu

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₂O₅

CAS Number:

63968-64-9

Molecular Weight:

282.33

NACRES:

NA.79

PubChem Substance ID:

57649481

UNSPSC Code:

12352205

MDL number:

MFCD00081057

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Quality Level

100

assay

98%

form

solid

optical activity

[α]20/D +76°, c = 0.5 in methanol

mp

156-157 °C (lit.)

antibiotic activity spectrum

parasites, viruses

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

mode of action

enzyme | inhibits

SMILES string

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

InChI

1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

InChI key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

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Related Categories

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

Natural Products for Research and Discovery

General description

Artemisinin is extracted from sweet wormwood (Artemisia annua). It has anticancer, antiprotozoal and antiviral activities. Artemisinin is associated with brainstem encephalopathy.

Application

Artemisinin has been used:

in drug susceptibility assays
as a standard for its quantification from artemisinin from hairy roots
to check cell viability using 3-(4, 5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay
as an antimalarial agent to investigate the role of autophagy-related (ATG) genes throughout the P. falciparum asexual and sexual blood stages

Biochem/physiol Actions

Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000521369

0000383864

MKCW0906

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Multiple populations of artemisinin-resistant Plasmodium falciparum in Cambodia.

Olivo Miotto et al.

Nature genetics, 45(6), 648-655 (2013-04-30)

We describe an analysis of genome variation in 825 P. falciparum samples from Asia and Africa that identifies an unusual pattern of parasite population structure at the epicenter of artemisinin resistance in western Cambodia. Within this relatively small geographic area

The multifunctional autophagy pathway in the human malaria parasite, Plasmodium falciparum

Cervantes S, et al.

Autophagy, 10(1), 80-92 (2014)

Stimulation of artemisinin synthesis by combined cerebroside and nitric oxide elicitation in Artemisia annua hairy roots

Wang JW, et al.

Applied Microbiology and Biotechnology, 85(2), 285-292 (2009)

Artemether resistance in vitro is linked to mutations in PfATP6 that also interact with mutations in PfMDR1 in travellers returning with Plasmodium falciparum infections

Pillai DR, et al.

Malaria Journal, 11(1), 131-131 (2012)

New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata.

Pierre-Eric Campos et al.

Marine drugs, 17(3) (2019-03-17)

Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F (1), 6-bromo-8,1'-dihydro-isoplysin A (2) and 5,6-dibromo-8,1'-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the

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Global Trade Item Number

SKU	GTIN
361593-100MG	04061835541317

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