Arteether - CAS 75887-54-6
Catalog number:
75887-54-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C17H28O5
Molecular Weight:
312.41
COA:
Inquire
Targets:
Others
Description:
Artemotil is a fast acting blood schizonticide. It is a semi-synthetic derivative of artemisinin, which is a natural product of the Chinese plant Artemisia annua. It is used as the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases. It is currently only used as a second line drug in severe cases of malaria.
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Purity:
98%
Appearance:
White Solid
Synonyms:
Alpha Beta Arteether;(3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin;Artemotil;SM-22;10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin;β-Arteether;(+)-Arteether;Dihydroqinghaosu Ethyl Ether
Solubility:
DMSO: ≥ 30 mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Artemotil is used as the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases. It is currently only used as a second line drug in severe cases of malaria.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
372.4±42.0 °C | Condition: Press: 760 Torr
Melting Point:
80-82 °C
Density:
1.16±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
NLYNIRQVMRLPIQ-XQLAAWPRSA-N
InChI:
InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1
Canonical SMILES:
CCOC1C(C2CCC(C3C24C(O1)OC(CC3)(OO4)C)C)C
Current Developer:
It has been approved the listing.
1.alpha/beta-Arteether-induced mania in a predisposed adolescent.
Haq MZ1, Mishra BR, Goyal N, Sinha VK. Gen Hosp Psychiatry. 2009 Jul-Aug;31(4):391-3. doi: 10.1016/j.genhosppsych.2008.10.004. Epub 2008 Nov 22.
Artemisinin, by the name of Qinghaosu, has been used in China for the treatment of fever over the years. Recently, a number of artemisinin derivatives such as artesunate, artemether, dihydroartemisinin, and arteether have been developed and have found widespread clinical use because of their efficacy against resistant forms of all plasmodial species and a favorable side-effect profile. However, concerns have been expressed about the neurotoxic effects of artemisinin derivatives based on some animal and human studies. We present a case of alpha/beta-arteether-induced mania in an adolescent having a family history of chloroquine-induced psychosis to discuss the hereditary predispositions, possible mechanisms, management, and clinical implications of this rare adverse event.
2.1,2-Bis[(3,6,9-trimethyl-3,12-ep-oxy-3,4,5,5a,6,7,8,8a,9,10,12,12a-dodeca-hydro-pyrano[4,3-j][1,2]benzodioxepin-4-yl)-oxy]ethane.
Jia L, Yue Z, Lv D, Gao P. Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o661. doi: 10.1107/S1600536812005089. Epub 2012 Feb 10.
The title compound, C(32)H(50)O(10), prepared from a mixture of α- and β-dihydro-artemisinin, has two β-arteether moieties linked via an -OCH(2)CH(2)O- bridge, so that the mol-ecule is symmetric about the bridge. Each asymmetric unit contains a β-arteether moiety and an -OCH(2) group, which is only one-half of the mol-ecule. The endo-peroxide bridges of the parent compounds have been retained in each half of the diol-bridged dimer. The rings exhibit chair and twist-boat conformations.
3.New orally active derivatives of artemisinin with high efficacy against multidrug-resistant malaria in mice.
Singh C1, Chaudhary S, Puri SK. J Med Chem. 2006 Nov 30;49(24):7227-33.
A new series of ether derivatives of dihydroartemisinin have been prepared and evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in mice by oral route. These new derivatives 7-17 are highly lipophilic (log P in the range of 5.51 to 7.19) as compared with beta-arteether (log P 3.84), and several of them are two- to four-fold more active than beta-arteether. Among the ether derivatives, alpha-isomers are more active than the beta-isomers. The ether derivatives 12alpha and 14alpha, the most active compounds of the series, provided 100% protection to infected mice at 12 mg/kgx4 days. In this model beta-arteether provides 100% and 20% protection at 48 mg/kgx4 days and 24 mg/kgx4 days, respectively.
4.Association of heme oxygenase 1 with the restoration of liver function after damage in murine malaria by Plasmodium yoelii.
Dey S1, Mazumder S1, Siddiqui AA1, Iqbal MS1, Banerjee C1, Sarkar S1, De R1, Goyal M1, Bindu S1, Bandyopadhyay U2. Infect Immun. 2014 Aug;82(8):3113-26. doi: 10.1128/IAI.01598-14. Epub 2014 May 12.
The liver efficiently restores function after damage induced during malarial infection once the parasites are cleared from the blood. However, the molecular events leading to the restoration of liver function after malaria are still obscure. To study this, we developed a suitable model wherein mice infected with Plasmodium yoelii (45% parasitemia) were treated with the antimalarial α/β-arteether to clear parasites from the blood and, subsequently, restoration of liver function was monitored. Liver function tests clearly indicated that complete recovery of liver function occurred after 25 days of parasite clearance. Analyses of proinflammatory gene expression and neutrophil infiltration further indicated that hepatic inflammation, which was induced immediately after parasite clearance from the blood, was gradually reduced. Moreover, the inflammation in the liver after parasite clearance was found to be correlated positively with oxidative stress and hepatocyte apoptosis.
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CAS 75887-54-6 Arteether

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