Dihydroartemisinin ethyl ether

HCID 72416CAS 75887-54-6

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Grundinformationen

Standard-SMILES: CCO[C@H]1O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]([C@H]1C)[C@@]24OO3
InChIKey: NLYNIRQVMRLPIQ-BVCZABNKSA-N
Summenformel: C17H28O5
Durchschnittliche Molmasse: 312,4 g/mol
Monoisotopische Masse: 312,19367399

Namen und Bezeichner

Bevorzugter Name: Dihydroartemisinin ethyl ether
IUPAC: (4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
Englischer Name: Arteether
Summenformel: C17H28O5
Molmasse: 312.4

Namen und Synonyme

Dihydroartemisinin ethyl etherArtemotil [INN]Artemotil (INN)beta arteetherethoxy(trimethyl)[?]UNII-XGL7GFB9YISM 227109716-83-8NSC 665971Ethyl-ether-quinghaosuSCHEMBL1648554CHEMBL3560584

Weitere Namen anzeigen

Alpha Beta ArteetherArtemotilTAGLSM-22SM-227AreetherArteetheArteetherARPRINOCIDaArteether

NLYNIRQVMRLPIQ-BVCZABNKSA-NTox21_113883NCGC00253770-013,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-, (3S-(3alpha,5alpha,6alpha,8aalpha,9beta,10beta,12beta,12aalpha))-3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, decahydro-10-ethoxy-3,6,9-trimethyl-, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,12aR*))-CAS-75887-54-6WR-255131D07361

Datenbank-Bezeichner

CAS: 75887-54-6
PubChem CID: 72416
DTXSID: DTXSID6057821
ChEMBL: CHEMBL3560584

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,4
Polarare Oberfläche (TPSA): 46,2 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 2
Schwere Atome: 22
Formalladung: 0
Komplexität: 443

Physikochemische Eigenschaften

Schmelzpunkt: 80 · 80-820C
Siedepunkt: 372.4 · 372.4±42.0 °C(Predicted)
Dichte: 1.16 · 1.16±0.1 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
Löslichkeit: Chloroform (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand: Solid
Farbe: White
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
InChIKey: NLYNIRQVMRLPIQ-XQLAAWPRSA-N
SMILES: O1[C@]23[C@@]4([H])O[C@@](C)(CC[C@@]2([H])[C@H](C)CC[C@@]3([H])[C@@H](C)[C@@H](OCC)O4)O1
CAS Datenbank: 75887 · 75887-54-6

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: WGK 3
Speicherklasse: 13 - Non Combustible Solids
Hazard Classifications: Repr. 2

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungArteether reached the market in the Netherlands as a solution in sesame oil, administered by i.m. injection, for the treatment of severe malaria infections in children and adolescents. Artheether, a sesquiterpene acetal with an endoperoxide bridge, is an ether derivative of the naturally occuring compound artemisinin, the active component of Chinese herbal remedies. As the other structural analogs of artemisinin, such as artesunate or artemether, it acts rapidly against Plasmodium, the parasite responsible for the disease, during the early blood stage of its development. It also exhibits a gametocytocidal activity against Plasmodium falciparum, reducing its potential for transmission. Because the only controlled clinical studies had been performed in children and adolescents, this new antimalarial drug was only approved for young patients. Further studies in adults treated with 150 mg i.m. artemotil, once daily for three consecutive days, indicated that the drug was efficient, rapidly acting (parasite clearance time meanly 38 h) and well tolerated. A new promising achievement in the regression of malaria is the combination of artemisinin derivatives with other long-lived antimalarials as mefloquine or pyrimethamine/sulfa.

VerwendenDerivative of Artemisinin. Antimalarial