(1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane

• ChemBase ID: 154875
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@]42[C@H]1CC[C@](O3)(OO4)C)OC)C
• Canonical SMILES: CO[C@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
• 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
• InChIKey: SXYIRMFQILZOAM-HVNFFKDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecane
• IUPAC Traditional name: artemether
• Synonyms: Dihydroartemisinin methyl ether; Dihydroqinghaosu methyl ether; SM-224; Artemether; (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; Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin; Artemos; Artenam; Artesaph; Artesian; Falcidol; Gvither; Larither; Malartem; SM 224; β-Artemether; β-Dihydroartemisinin Methyl Ether; Artemether; (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

Database IDs

• CAS Number: 71963-77-4
• MDL Number: MFCD00866205
• PubChem SID: 162249013
• PubChem CID: 68911

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.481392
• LogD (pH = 7.4): 3.481392
• Log P: 3.481392
• Molar Refractivity: 74.6605 cm^3
• Polarizability: 30.79904 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥20 mg/mL; Methanol
• Apperance: off-white to light brown powder; White to Off-White Solid
• Melting Point: 86-88°C
• Optical Rotation: [α]/D +155 to +175°, c = 0.5 in methanol
• Hydrophobicity(logP): 3.055

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KD4165000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C16H26O5

DETAILS

Sigma Aldrich - A9361

Biochem/physiol Actions
Artemether is a methyl ether derivative of artemisinin. It is used against multi-drug resistant strains of the malaria parasite, Plasmodium falciparum, and shows potential in treatment of schistosomiasis.1

Toronto Research Chemicals - A777400

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

REFERENCES

• Hombhanje, F., et al.: Pharma., 3, 3581 (2010)
• Michael, O., et al.: Malaria J., 9, 335 (2010)
• Cesar, I., et al.: J. Pharm. Biomed. Anal., 54, 114 (2010)