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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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Properties

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

361593-VAR: + 361593-BULK: + 361593-100MG:

jan

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Artemisinins for schistosomiasis and beyond.

Jürg Utzinger et al.

Current opinion in investigational drugs (London, England : 2000), 8(2), 105-116 (2007-03-03)

Schistosomiasis is a significant health issue caused by a blood fluke that affects more than 200 million individuals worldwide, over half of whom suffer from disease-associated symptoms. In areas of high burden, disease is mainly managed by controlling morbidity with

Antiprotozoal drugs

Simooya OO

Side Effects of Drugs Annual, 30, 336-342 (2008)

Deciphering genetic regulation of CD14 by SP1 through characterization of peripheral blood mononuclear transcriptome of P. faiciparum and P. vivax infected malaria patients

Chakraborty B, et al.

EBioMedicine, 37, 442-452 (2018)

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