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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24O5
Molecular Weight 284.3481
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTENIMOL

SMILES

[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@H](O)[C@@H]2C)O4

InChI

InChIKey=BJDCWCLMFKKGEE-ISOSDAIHSA-N
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H24O5
Molecular Weight 284.3481
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

Artemether is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with lumefantrine for improved efficacy against malaria. Artemether is rapidly metabolized into an active metabolite dihydroartemisinin (DHA). The antimalarial activity of artemether and DHA has been attributed to endoperoxide moiety. Artemethe involves an interaction with ferriprotoporphyrin IX (“heme”), or ferrous ions, in the acidic parasite food vacuole, which results in the generation of cytotoxic radical species. The generally accepted mechanism of action of peroxide antimalarials involves interaction of the peroxide-containing drug with heme, a hemoglobin degradation byproduct, derived from proteolysis of hemoglobin. This interaction is believed to result in the formation of a range of potentially toxic oxygen and carbon-centered radicals. Other mechanisms of action for artemether include their ability to reduce fever by production of signals to hypothalamus thermoregulatory center. Now, recent research has shown the presence of a new, previously unknown cyclooxygenase enzyme COX-3, found in the brain and spinal cord, which is selectively inhibited by artemether, and is distinct from the two already known cyclooxygenase enzymes COX-1 and COX-2. It is now believed that this selective inhibition of the enzyme COX-3 in the brain and spinal cord explains the ability of artemether in relieving pain and reducing fever which is produced by malaria. The most common adverse reactions in adults (>30%) are headache, anorexia, dizziness, asthenia, arthralgia and myalgia.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.5 nM [EC50]
24.0 nM [IC50]
79.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eurartesim
Curative
Eurartesim
Curative
Artemisinin
Curative
COARTEM

Cmax

ValueDoseCo-administeredAnalytePopulation
60 ng/mL
80 mg single, oral
ARTEMETHER plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
146 ng × h/mL
80 mg single, oral
ARTEMETHER plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
80 mg single, oral
ARTEMETHER plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
4.6%
80 mg single, oral
ARTEMETHER plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Adults and children: 25 mg/kg on the first day followed by 12.5 mg/kg on the second and third days in combination with mefloquine (15 mg/kg) in a single dose on the second day. In some areas, a higher dose (25 mg/kg) of mefloquine may be required for a cure to be obtained.
Route of Administration: Oral
In Vitro Use Guide
Artemisinine was active against 3 chloroquine-resistant strains of Plasmodium falciparum, strains K1 and T996 from Thailand and LS21 from India, with complete growth inhibition at 10(-7) M.
Substance Class Chemical
Record UNII
6A9O50735X
Record Status Validated (UNII)
Record Version