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Compound Detail

CHEMBL566534

ARTEMETHER
💊 Approved Drug
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💊 Approved Drug
CO[C@H]1O[C@@H]2O[C@@]3(C)CC[C@H]4[C@H](C)CC[C@@H]([C@H]1C)[C@@]24OO3

Basic Information

ChEMBL ID CHEMBL566534
Name ARTEMETHER
Phase Approved
Structure Type MOL
InChI Key SXYIRMFQILZOAM-HVNFFKDJSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL307261

Known Names

.beta.-artemether Artemetero Artemether Artemether component of coartem Artemetheri Artemetherum Artesaph Dihydroartemisinin impurity g Falcidol Gvither Larither Malartem +5 more
16
Targets
59
Activities
2
Assay Types
17
PK Parameters
20
Publications
17
Known Names
7
Indications
1
Mechanisms

Molecular Properties

298.4
MW (Da)
2.84
ALogP
5
HBA
0
HBD
46.1
PSA (Ų)
0.70
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class Prodrug
USAN Stem arte-
USAN Year 2008

Extended Properties

Molecular Formula C16H26O5
MW 298.38
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 3.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ferriprotoporphyrin IX inhibitor INHIBITOR Ferriprotoporphyrin IX

Indications

Malaria Fever Malaria, Falciparum Malaria, Vivax Schistosomiasis haematobia HIV Infections Neoplasms

ATC Classification

P01BE02
artemether
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 58 meas. best 8.9
EC50 1 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 8.9 8.3744 1.3 39
Plasmodium berghei
CHEMBL612653
IC50 8.52 8.08 3.0 2
Toxoplasma gondii
CHEMBL612888
IC50 6.51 6.51 310.0 1
Unchecked
CHEMBL612545
IC50 6.46 6.46 351.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.75 5.1433 1780.0 3
T-cell
CHEMBL614309
IC50 5.42 5.42 3820.0 1
Cytomegalovirus
CHEMBL613134
EC50 5.28 5.28 5300.0 1
Prostaglandin E synthase 2
CHEMBL4411
IC50 5.14 5.14 7200.0 1
SK-MEL-2
CHEMBL614917
IC50 5.14 5.14 7240.0 1
SK-OV-3
CHEMBL614925
IC50 5.09 5.09 8030.0 1
A549
CHEMBL392
IC50 5.07 5.07 8540.0 1
HCT-116
CHEMBL394
IC50 5.07 5.07 8600.0 1
XF498
CHEMBL613533
IC50 5.04 5.04 9100.0 1
HCT-15
CHEMBL612263
IC50 5.01 5.01 9660.0 1
Leishmania major
CHEMBL612879
IC50 4.65 4.65 22540.0 1
Leishmania donovani
CHEMBL367
IC50 4.37 4.205 42290.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 168.0 ng.hr.mL-1 Homo sapiens
AUC 382.0 ng.hr.mL-1 Homo sapiens
CL 114.0 mL.min-1.kg-1 Mus musculus
Cmax 113.95 nM Homo sapiens
Cmax 398.82 nM Homo sapiens
F 1.4 % Rattus norvegicus
F 1.4 % Mus musculus
F 1.4 % Rattus norvegicus
F 1.4 % Rattus norvegicus
T1/2 2.0 hr -
T1/2 52.2 - Rattus norvegicus
T1/2 0.8667 hr Mus musculus
T1/2 3.9 hr Homo sapiens
T1/2 1.9 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 11.0 hr -
Vd 8.0 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 1.26 nM 8.9 Antimalarial activity against Plasmodium falciparum 3D7 infected human erythrocy... 18845438
Plasmodium falciparum IC50 = 1.26 nM 8.9 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 inf... 19251414
Plasmodium falciparum IC50 = 1.92 nM 8.72 Intrinsic equimolar activity against Plasmodium falciparum W2 Indochina relative... 3279208
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antimalarial activity against Plasmodium falciparum NF54 33508479
Plasmodium falciparum IC50 = 2.11 nM 8.68 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 by... 19136263
Plasmodium falciparum IC50 = 2.3 nM 8.64 Antiplasmodial activity against chloroquine-resistant asexual erythrocyte stage ... 27448920
Plasmodium falciparum IC50 = 2.3 nM 8.64 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 ... 32987134
Plasmodium falciparum IC50 = 2.34 nM 8.63 Intrinsic equimolar activity against Plasmodium falciparum D6 (Sierra Leone) rel... 3279208
Plasmodium falciparum IC50 = 2.5 nM 8.6 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 18268087
Plasmodium falciparum IC50 = 2.8 nM 8.55 Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum by [3... 18260613
Plasmodium berghei IC50 = 3.0 nM 8.52 Antiplasmodial activity against Plasmodium berghei ANKA early trophozoite stage ... 26367273
Plasmodium falciparum IC50 = 3.2 nM 8.49 Antimalarial activity against Plasmodium falciparum 3D7 18243702
Plasmodium falciparum IC50 = 3.2 nM 8.49 Antimalarial activity against Plasmodium falciparum 3D7 18341274
Plasmodium falciparum IC50 = 3.34 nM 8.48 Inhibitory concentration against Plasmodium falciparum W2 Indochina 3279208
Plasmodium falciparum IC50 = 3.42 nM 8.47 In vitro antimalarial activity against chloroquine-sensitive Plasmodium falcipar... 11141088
Plasmodium falciparum IC50 = 3.4 nM 8.47 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 (Th... 19957999
Plasmodium falciparum IC50 = 3.5 nM 8.46 Antiplasmodial activity against Plasmodium falciparum FCB1 assessed as inhibitio... 34213340
Plasmodium falciparum IC50 = 3.45 nM 8.46 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 19251414
Plasmodium falciparum IC50 = 3.5 nM 8.46 In vitro inhibitory concentration against chloroquine-resistant Plasmodium falci... 14998331
Plasmodium falciparum IC50 = 3.53 nM 8.45 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 by ... 19136263

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 346
34243044 10.1016/j.bmc.2021.116293 Saccharomyces cerevisiae 22
16033274 10.1021/jm049040u Mus musculus 14
20813948 10.1126/science.1193225 Plasmodium berghei 13
34243044 10.1016/j.bmc.2021.116293 Candida albicans 13
17242150 10.1128/aac.00967-06 Plasmodium vinckei petteri 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17404003 10.1128/aac.01479-06 Plasmodium falciparum 8
19841149 10.1128/aac.00679-09 Homo sapiens 6
12773055 10.1021/jm020584a Mus musculus 6
23425037 10.1021/jm400058j Plasmodium berghei 6
33508479 10.1016/j.ejmech.2021.113193 Plasmodium falciparum 6
19186946 10.1021/jm801484v Plasmodium berghei 6
34243044 10.1016/j.bmc.2021.116293 Unchecked 4
26367273 10.1021/acs.jmedchem.5b01036 Plasmodium berghei 4
16033274 10.1021/jm049040u ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
14998331 10.1021/jm030947m Rattus norvegicus 4
3279208 10.1021/jm00398a026 Plasmodium falciparum 4

Data from ChEMBL 36 via Core Engine