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
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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q8I3Z5 Gene ID: 812831.0 Gene Symbol: TCTP Target Organism: Plasmodium falciparum (isolate 3D7) Sources: https://www.google.com/patents/US20060141024 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ARTECEF Approved UseSevere P. falciparum malaria infection. |
PubMed
Title | Date | PubMed |
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Inhibition of growth of Toxoplasma gondii by qinghaosu and derivatives. | 1990 Oct |
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In vitro effects of artemisinin ether, cycloguanil hydrochloride (alone and in combination with sulfadiazine), quinine sulfate, mefloquine, primaquine phosphate, trifluoperazine hydrochloride, and verapamil on Toxoplasma gondii. | 1994 Jun |
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Bile acid-based 1,2,4-trioxanes: synthesis and antimalarial assessment. | 2012 Dec 13 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16231969
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.
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WHO-ATC |
P01BE04
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ARTEMOTIL
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PRIMARY | Description: A white or almost white, crystalline powder. Solubility: Practically insoluble in water; sparingly soluble in dichloromethane R, ethanol (~750 g/l) TS and methanol R; soluble inarachis oil R and sesame oil R. Category: Antimalarial drug. Storage: Artemotil should be kept in a well-closed container, protected from light. Labelling: The designation Artemotil for parenteral use indicates that the substance complies with the additional requirements and may be used for parenteral administration. Additional information: The parenteral form is normally intended for intramuscular administration. Requirement: Artemotil contains not less than 97.0% and not more than the equivalent of 102.0% of C17H28O5 calculated with reference to the dried substance. | ||
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ARTEMOTIL
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)