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Details

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
Structure of ARTEMOTIL

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ARTECEF

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
XGL7GFB9YI
Record Status Validated (UNII)
Record Version