Artemisinin

Artemisinin

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Artemisinin
Category Enzyme inhibitors
Catalog number BBF-04621
CAS 63968-64-9
Molecular Weight 282.33
Molecular Formula C15H22O5
Purity 98% by HPLC

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BBF-04621 100 g $199 In stock

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Description

Artemisinin is a natural product originally isolated from plants of the genus Artemisia. It effectively kills malarial parasites of the genus Plasmodium. It is usually used in combination therapy for the treatment of malaria. Artemisinin is also used against a wide range of trematodes, including Schistosoma. Artemisinin is an inhibitor of human NOS2 (iNOS) with anticancer activity.

Specification

Synonyms (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epox12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one; Artemisine; Arteannuin; Huanghuahaosu; QHS; Qinghaosu; (+)-Artemisinin
Storage Store at 2-8°C
IUPAC Name (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
Canonical SMILES CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C
InChI 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
Source Artemisia annua (plant extract)

Properties

Appearance White Solid
Antibiotic Activity Spectrum Parasites
Boiling Point 389.9°C at 760 mmHg
Melting Point 156-157°C
Flash Point 172°C
Density 1.24 g/cm3
Solubility Soluble in chloroform, acetone, ethyl ether, ethyl acetate, insoluble in water
LogP 2.9

Reference Reading

1.Efficacy of Artesunate-mefloquine for Chloroquine-resistant Plasmodium vivax Malaria in Malaysia: An Open-label, Randomized, Controlled Trial.
Grigg MJ1, William T2, Menon J3, Barber BE1, Wilkes CS1, Rajahram GS4, Edstein MD5, Auburn S6, Price RN7, Yeo TW8, Anstey NM9. Clin Infect Dis. 2016 Apr 22. pii: ciw121. [Epub ahead of print]
BACKGROUND:  Chloroquine (CQ)-resistant Plasmodium vivax is increasingly reported throughout southeast Asia. The efficacy of CQ and alternative artemisinin combination therapies (ACTs) for vivax malaria in Malaysia is unknown.
2.Artemisinin and its derivatives can significantly inhibit lung tumorigenesis and tumor metastasis through Wnt/β-catenin signaling.
Tong Y1,2, Liu Y1,2, Zheng H2, Zheng L1,2, Liu W1,2, Wu J2, Ou R2, Zhang G2, Li F2, Hu M2,3, Liu Z1,2, Lu L2. Oncotarget. 2016 Apr 22. doi: 10.18632/oncotarget.8920. [Epub ahead of print]
Non-small-cell lung cancer (NSCLC) is the most prevalent malignancy worldwide given its high incidence, considerable mortality, and poor prognosis. The anti-malaria compounds artemisinin (ART), dihydroartemisinin (DHA), and artesunate (ARTS) reportedly have anti-cancer potential, although the underlying mechanisms remain unclear. In this work, we used flow cytometry to show that ART, DHA, and ARTS could inhibit the proliferation of A549 and H1299 cells by arresting cell cycle in G1 phase. Meanwhile, tumor malignancy including migration, invasion, cancer stem cells, and epithelial-mesenchymal transition were also significantly suppressed by these compounds. Furthermore, ART, DHA, and ARTS remarkably decreased tumor growth in vivo. By using IWP-2, the inhibitor of Wnt/β-catenin pathway, and Wnt5a siRNA, we found that ART, DHA, and ARTS could render tumor inhibition partially dependent on Wnt/β-catenin inactivation. These compounds could strikingly decrease the protein level of Wnt5-a/b and simultaneously increase those of NKD2 and Axin2, ultimately resulting in β-catenin downregulation.
3.Artesunate inhibits adipogeneis in 3T3-L1 preadipocytes by reducing the expression and/or phosphorylation levels of C/EBP-α, PPAR-γ, FAS, perilipin A, and STAT-3.
Jang BC1. Biochem Biophys Res Commun. 2016 Apr 21. pii: S0006-291X(16)30614-3. doi: 10.1016/j.bbrc.2016.04.109. [Epub ahead of print]
Differentiation of preadipocyte, also called adipogenesis, leads to the phenotype of mature adipocyte. However, excessive adipogenesis is closely linked to the development of obesity. Artesunate, one of artemisinin-type sesquiterpene lactones from Artemisia annua L., is known for anti-malarial and anti-cancerous activities. In this study, we investigated the effect of artesunate on adipogenesis in 3T3-L1 preadipocytes. Artesunate strongly inhibited lipid accumulation and triglyceride (TG) synthesis during the differentiation of 3T3-L1 preadipocytes into adipocytes at 5 μM concentration. Artesunate at 5 μM also reduced not only the expressions of CCAAT/enhancer-binding protein-α (C/EBP-α), peroxisome proliferator-activated receptor-γ (PPAR-γ), fatty acid synthase (FAS), and perilipin A but also the phosphorylation levels of signal transducer and activator of transcription-3 (STAT-3) during adipocyte differentiation. Moreover, artesunate at 5 μM reduced leptin, but not adiponectin, mRNA expression during adipocyte differentiation.
4.Artemisinin and its derivatives can significantly inhibit lung tumorigenesis and tumor metastasis through Wnt/β-catenin signaling.
Tong Y1,2, Liu Y1,2, Zheng H2, Zheng L1,2, Liu W1,2, Wu J2, Ou R2, Zhang G2, Li F2, Hu M2,3, Liu Z1,2, Lu L2. Oncotarget. 2016 Apr 22. doi: 10.18632/oncotarget.8920. [Epub ahead of print]
Non-small-cell lung cancer (NSCLC) is the most prevalent malignancy worldwide given its high incidence, considerable mortality, and poor prognosis. The anti-malaria compounds artemisinin (ART), dihydroartemisinin (DHA), and artesunate (ARTS) reportedly have anti-cancer potential, although the underlying mechanisms remain unclear. In this work, we used flow cytometry to show that ART, DHA, and ARTS could inhibit the proliferation of A549 and H1299 cells by arresting cell cycle in G1 phase. Meanwhile, tumor malignancy including migration, invasion, cancer stem cells, and epithelial-mesenchymal transition were also significantly suppressed by these compounds. Furthermore, ART, DHA, and ARTS remarkably decreased tumor growth in vivo. By using IWP-2, the inhibitor of Wnt/β-catenin pathway, and Wnt5a siRNA, we found that ART, DHA, and ARTS could render tumor inhibition partially dependent on Wnt/β-catenin inactivation. These compounds could strikingly decrease the protein level of Wnt5-a/b and simultaneously increase those of NKD2 and Axin2, ultimately resulting in β-catenin downregulation.

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