Stereochemistry | ABSOLUTE |
Molecular Formula | C17H28O5 |
Molecular Weight | 312.4012 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@H](OCC)[C@@H]2C)O4
InChI
InChIKey=NLYNIRQVMRLPIQ-XQLAAWPRSA-N
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
Molecular Formula | C17H28O5 |
Molecular Weight | 312.4012 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Artemotil (also known as beta-arteether) is an antimalarial artemisinin derivative, approved for the treatment of severe cases of P. falciparum malaria. The mixture of artemotil and alpha-arteether is used in patients with cerebral malaria. Most of the artemisinin compounds including artemotil are metabolized into dihydroartemisinin, which is responsible for antimalarial activity. These compounds contain stable endoperoxide bridge. The antimalarial activity of the drug thus is dependent on the cleavage of the endoperoxide by intraparasitic heme. The cleaved endoperoxide ultimately becomes a carbon centered free radical, which then functions as an alkylating agent, reacting with both heme and parasitic proteins (but not DNA). In P. falciparum, one of the principal alkylation target is the translationally controlled tumor protein (DHA-TCTP) homolog. Some intraparasitic TCTP is situated in the membrane surrounding the heme-rich food vacuole, where heme could catalyse the formation of drug-protein (DHA-TCTP) adduct and inhibit the parasite's growth.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
The initial dose consists of an injection of 4.8 mg artemotil per kg body weight evenly divided over both anterior thighs. The follow-up doses consist of 1.6 mg per kg body weight after 6, 24, 48 and 72 hours in alternating thighs.
Route of Administration:
Intramuscular
The microassay for minimum inhibitory concentrations (MICs) of arteether isomers, including artemotil, was carried out in 96-well microtitre plates against four inhouse maintained strains of P. falciparum (NF54, 3D7, RKL9 and JDP8) in vitro. For the assay, the 2-fold serial dilutions of arteether isomers in the 0.5-16 ug/L concentration range in three replicate wells were incubated with parasitised cell preparation at 37C in a candle jar for 30-40 h.