10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

• ChemBase ID: 4435
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: CC1CCC2C(C)C(OC)OC3C42C1CCC(OO4)(O3)C
• Canonical SMILES: COC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)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
• InChIKey: SXYIRMFQILZOAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane
• IUPAC Traditional name: artemisinine,methyl ether (α)
• Brand Name: Coartem
• Synonyms: Dihydroartemisinin methyl ether; Artemether

Database IDs

• CAS Number: 71963-77-4
• PubChem SID: 160967867
• PubChem CID: 500199

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.02
• LOG S: -2.81
• Solubility (Water): 4.57e-01 g/l

DETAILS

DrugBank - DB06697

• Drug Groups: approved
• Description: Artemether is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with lumefantrine for improved efficacy. This combination therapy exerts its effects against the erythrocytic stages of Plasmodium spp. and may be used to treat infections caused by P. falciparum and unidentified Plasmodium species, including infections acquired in chloroquine-resistant areas.
• Indication: 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 the Plasmodium species has not been identified. Indicated for use in adults and children greater than 5 kg.
• Pharmacology: In the body, artemether is metabolized into the active metabolite metabolite dihydroartemisinin. The drug works against the erythrocytic stages of P. falciparum by inhibiting nucleic acid and protein synthesis. Artemether is administered in combination with lumefantrine for improved efficacy. Artemether has a rapid onset of action and is rapidly cleared from the body. It is thought that artemether provides rapid symptomatic relief by reducing the number of malarial parasites. Lumefantrine has a much longer half life and is believed to clear residual parasites.
• Toxicity: Common side effects of combination artemether/lumefantrine therapy in adults include headache, anorexia, dizziness, and asthenia. Common side effects in children include pyrexia, cough, vomiting, anorexia, and headache. Possible serious adverse effects include QT prolongation, bullous eruption, urticaria, splenomegaly (9%), hepatomegaly (adults, 9%; children, 6%), hypersensitivty reaction, and angioedema.
• Affected Organisms: Plasmodium
• Biotransformation: Rapidly metablized to its active metabolite, dihydroartemisinin.
• Absorption: Food increases absorption.
• Half Life: Artemether, 1.6 +/- 0.7 and 2.2 +/- 1.9 hr; Dihydroartemisinin, 1.6 +/- 0.6 and 2.2 +/- 1.5 hr
• Protein Binding: Artemether, 95.4%; Dihydroartemisinin, 47-76%
• References: Artemether and Lumefantrine (2010). AHFS Drug Information [Electronic versionb]. Retrieved October 24, 2010.; Artemether/Lumefantrine (2010). DrugPoints? System [Electronic version]. Retrieved October 24, 2010.; Novartis. Coartem (artemether/lumefantrine) tablets prescribing information. East Hanover, NJ; 2010 Feb.
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Novartis. Coartem (artemether/lumefantrine) tablets prescribing information. East Hanover, NJ; 2010 Feb.
• Artemether and Lumefantrine (2010). AHFS Drug Information [Electronic versionb]. Retrieved October 24, 2010.
• Artemether/Lumefantrine (2010). DrugPoints? System [Electronic version]. Retrieved October 24, 2010.