Dihydroartemisinin ethyl ether (HCID 72416)

名称と識別子

優先名称: 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
現地名: アルテモチル
英語名: Arteether
分子式: C17H28O5
分子量: 312.4

名称と別名

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

名称をさらに表示

アルテエーテル(3R,12aR)-3,6α,9β-トリメチル-10β-エトキシ-3β,12α-エポキシ-3,4,5,5aα,6,7,8,8aα,9,10-デカヒドロピラノ[4,3-j]-1,2-ベンゾジオキセピンα-アルテエーテルアルテモチル(3R,5aα,8aα,12aR)-10β-エトキシデカヒドロ-3,6α,9β-トリメチル-3β,12α-エポキシピラノ[4,3-j]-1,2-ベンゾジオキセピンアルテエテルアルテーター(3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-エトキシデカヒドロ-3,6,9-トリメチル-3,12-エポキシピラノ[4,3-j]-1,2-ベンゾジオキセピン(1R,4S,5R,8S,9R,10S,12R,13R)-10-エトキシ-1,5,9-トリメチル-11,14,15,16-テトラオキサテトラシクロ[10.3.1.04,13.08,13]ヘキサデカン(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-トリメチル-10-エトキシ-3,12-エポキシ-3,4,5,5a,6,7,8,8a,9,10-デカヒドロピラノ[4,3-j]-1,2-ベンゾジオキセピン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

データベース識別子

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

物性

構造計算による物性

XLogP: 3.4
極性表面積: 46.2 Å²
水素結合供与体数: 0
水素結合受容体数: 5
回転可能結合数: 2
重原子数: 22
形式電荷: 0
複雑度: 443

物理化学的性質

融点: 80 · 80-820C
比旋光度: 21 · D21 +154.5° (c = 1.0 in CHCl3)
沸点: 372.4 · 372.4±42.0 °C(Predicted)
比重(密度): 1.16 · 1.16±0.1 g/cm3(Predicted)
貯蔵温度: 2 · Sealed in dry,2-8°C
溶解性: クロロホルム（微量）、酢酸エチル（微量）
外見: 個体
色: 白い
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 データベース: 75887 · 75887-54-6

化学的性質

化学的特性White Crystalline Solid

安全と法規制

安全データ

wgk: WGK 3
Hazard Classifications: Repr. 2
ストレージクラス: 13 - Non Combustible Solids

化学と産業

応用分野 · 2 件

説明Arteether 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.

使用Derivative of Artemisinin. Antimalarial