3D Mol Similar

Artemether

: CAS No.: 71963-77-4; Molecular Weight：298.379; Modify Date.: 2024-03-31 16:06; Introduction: Derivative of Artemisinin (A777500). Antimalarial, used to treat strains of malaria which are multi-drug resistant. View more+

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1. Names and Identifiers

: 1.1 Name; Artemether; 1.2 Synonyms; (1R,4S,5R,8S,9R,10S,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0.0]hexadecane (1R,4S,5R,8S,9R,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-methoxy-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene (4S,5R,8S,9R,10S,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0.0]hexadecane [3r-(3r,5as,6s,8as,9r,10r,12s,12ar**)]-decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j]-1,2-benzodioxepin 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)- 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,12R,12aR)- 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (5aS,6R,8aS,9R,10S,12R,12aR)- ArtemetherC16H26O5 ArteMos ArtenaM Artesaph Artesian ARTHEMETER Artimether cgp56696 dihydroartemisininmethylether Dihydroqinghaosu Methyl Ether Falcidol Gvither Larither MalarteM methyl-dihydroartemisinine MFCD00866205 Paluther Pharmakon1600-01505032 SM-224; View all

1.3 CAS No.: 71963-77-4

1.4 CID: 68911

1.5 EINECS(EC#): 663-549-0

1.6 Molecular Formula: C16H26O5 (isomer)

1.7 Inchi: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1

1.8 InChIkey: SXYIRMFQILZOAM-HVNFFKDJSA-N

1.9 Canonical Smiles: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C

1.10 Isomers Smiles: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C

2. Properties

2.1 Density: 1.18

2.1 Melting point: 86-89

2.1 Boiling point: 358 °C

2.1 Refractive index: 1.518

2.1 Flash Point: 141 °C

2.1 Precise Quality: 298.17800

2.1 PSA: 46.15000

2.1 logP: 2.84080

2.1 Solubility: DMSO: ≥20mg/mL

2.2 Appearance: White to Almost white powder to crystal

2.3 Chemical Properties: White Solid

2.4 Color/Form: off-white to light brown

2.5 Physical: Solid

2.6 Water Solubility: Insoluble

2.7 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: ChEBI: An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falciprum malaria.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 26 companies from 3 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria by 1 of 26 companies. For more detailed information, please visit ECHA C&L website

Of the 2 notification(s) provided by 25 of 26 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501; View all

3.3 Methods of Manufacturing: Prepn: Derivative of artemisinin;. Y Li et al; Ko Hseuh Tung Pao 24: 667 (1979)

3.4 Usage: Derivative of Artemisinin (A777500). Antimalarial, used to treat strains of malaria which are multi-drug resistant.

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: 22

4.1 Safety Statements: 24/25

4.1 Hazard Declaration: H302

4.1 RIDADR: OTH

4.1 Safety Profile: Poison by intramuscular route.Experimental reproductive effects. When heated todecomposition it emits acrid smoke and irritating fumes. Artemether Preparation Products And Raw materials Preparation Products

4.2 Caution Statement: P301 + P312 + P330

4.2 WGK Germany: 3

4.2 RTECS: KD4165000

4.2 Safety: Poison by intramuscular route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

4.3 Specification: ?Artemether (CAS NO.71963-77-4) is also named as (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin ; Artemetero ; Artemetero [INN-Spanish] ; Artemetherum ; Artemetherum [INN-Latin] ; Artemisininelactol methyl ether ; Dihydroartemisinin methyl ether ; Dihydroquinghaosu methyl ether ; HSDB 7456 ; Methyl-dihydroartemisinine ; NSC 665970 ; SM 224 ; UNII-C7D6T3H22J ; beta-Artemether ; beta-Dihydroartemisinin methyl ether?.?Artemether (CAS NO.71963-77-4) is?toxic. It is flammable. It will produce Stimulate smoke when buring. So the storage environment should be ventilate, low-temperature and dry.

4.4 Toxicity: LD50 i.m. in mice: 263 mg/kg (China Cooperative Research Group on Qinghaosu)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

71963-77-4Total: 7 Synthesis Route

77-76-9 170 Suppliers

81496-81-3 84 Suppliers

71963-77-4 358 Suppliers

Literatures:
WO2009/109989 A1, ; Page/Page column 14 ;
Yield: null

81496-81-3 84 Suppliers

149-73-5 156 Suppliers

71963-77-4 358 Suppliers

Literatures:
CALYX CHEMICALS AND PHARMACEUTICALS LTD. Patent: WO2009/109989 A1, 2009 ; Location in patent: Page/Page column 9-10 ;
Yield: ~75%

116-11-0 132 Suppliers

81496-81-3 84 Suppliers

71963-77-4 358 Suppliers

Literatures:
WO2009/109989 A1, ; Page/Page column 12 - 13 ;
Yield: null

View all

8. Precursor and Product

precursor:

1445-45-0

81496-81-3

71939-50-9

53562-86-0

116-11-0

3976-69-0

77-76-9

149-73-5

9. Other Information

9.0 Merck: 14,815

9.1 Description: Artemether is an antiparasitic compound and a derivative of artemisinin (Item No. 11816). It induces mortality in adult wild-type and pfatp6-mutant P. falciparum but the efficacy is decreased in the mutants (IC₅₀s = 8.2 and 13.5 nM, respectively). Artemether reduces parasitemia in P. falciparum-infected monkeys and P. berghei-infected mice with 50% curative dose (CD₅₀) values of 7.1 and 55 mg/kg, respectively. It also reduces the worm burden of S. mansoni trematodes in mice when used at doses ranging from 200 to 500 mg/kg. Formulations containing artemether have been used in the treatment of malaria.; View all

9.2 Chemical Properties: White Solid

9.3 Uses: Derivative of Artemisinin (A777500). Antimalarial, used to treat strains of malaria which are multi-drug resistant.

9.4 Uses: atypical antidepressant, norepinephrine and dopamine reuptake inhibitor, and nicotinic antagonist

9.5 Uses: Artemether and lumefantrine combination therapy is indicated for the treatment of acute uncomplicated malaria caused by Plasmodium falciparum, including malaria acquired in chloroquine-resistant areas. May also be used to treat uncomplicated malaria when

9.6 Definition: ChEBI: An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falcip rum malaria.

9.7 General Description: Artemisinin (ART) is a natural compound present in Artemisia annua, a traditional Chinese plant.

10. Computational chemical data

Molecular Weight: 298.379g/mol
Molecular Formula: C₁₆H₂₆O₅
Compound Is Canonicalized: True
XLogP3-AA: 3.1
Exact Mass: 298.17802393
Monoisotopic Mass: 298.17802393
Complexity: 429
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 46.2
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAAAAAAAA0SIAABIkAAACQAAAAGgAABAAADUSwgAMCCAAABAAAAAAAAAAAAAAAAAAAAAAAAAARAAIAAAAiAAAEAAAGAAHA4PwOgAAAAAAAAACAAAYAADAAAAAAAAAAAA==

11. Question & Answer

Does Artemether produce irritating smoke when burned? Apr 26 2023
Artemether is a highly important compound in the fields of chemical engineering and biopharmaceuticals. It is commonly stored in large quantities by pharmaceutical companies and chemical plants for da..
How much does Artemether cost and who should avoid taking it? Jun 22 2022
The presence of C-reactive protein and erythrocyte sedimentation rate can lead to the development of malaria. Artemether is a prescription drug used to treat chloroquine-resistant severe malaria and d..
What is the preparation method for the new antimalarial drug compound Artemether? Feb 06 2022
Drug-resistant malaria is increasing day by day around the world. More than 70% of Plasmodium falciparum parasites are resistant to existing antimalarial drugs such as chloroquine, chlorophenoquine, p..
What can cause artesian well water to smell? Jun 15 2021
Recently, our water from the artesian well started to smell (again). It only smells bad for only few seconds than the smell disappear. We have sulfur-iron removal system, water softener, UV lamp. Onl..

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