Dihydroartemisinin ethyl ether

HCID 72416

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Basic information

CAS: 75887-54-6
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
Molecular formula: C17H28O5
Average molar mass: 312.4 g/mol
Monoisotopic mass: 312.19367399

Names & identifiers

Preferred 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
English name: Arteether
Molecular formula: C17H28O5
Molecular weight: 312.4

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 3.4
Topological polar surface area: 46.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 22
Formal charge: 0
Complexity: 443

Physicochemical properties

Melting point: 80 · 80-820C
alpha: 21 · D21 +154.5° (c = 1.0 in CHCl3)
Boiling point: 372.4 · 372.4±42.0 °C(Predicted)
Density: 1.16 · 1.16±0.1 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
color: White
optical activity: 148 to · [α]/D +148 to +165°, c =1 in chloroform-d
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 DataBase Reference: 75887 · 75887-54-6
FDA UNII: 7 GFB9YI · XGL7GFB9YI
ATC code: 1 BE04 · P01BE04
UNSPSC Code: 51111800 · 51111800
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06,GHS02
Signal word: Danger
Hazard statements: 301 · H301+H311+H331-H226
Precautionary statements: 501 · P501-P261-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P361+P364-P303+P361+P353-P301+P310+P330-P304+P340+P311-P403+P233-P403+P235-P405
WGK Germany: 3 · WGK 3
Storage Class: 13 · 13 - Non Combustible Solids
Hazard Classifications: 2 · Repr. 2

Safety & regulation

Safety data

wgk: WGK 3
Signal word: Danger
Symbol(GHS): GHS06,GHS02
Storage Class: 13 - Non Combustible Solids
Hazard statements: H301+H311+H331-H226
Hazard Classifications: Repr. 2
Precautionary statements: P501-P261-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P361+P364-P303+P361+P353-P301+P310+P330-P304+P340+P311-P403+P233-P403+P235-P405

Chemistry & industry

Applications · 2 items

DescriptionArteether 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.

UsesDerivative of Artemisinin. Antimalarial