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Compound Detail

CHEMBL307261

ARTENIMOL
🧪 Phase III
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🧪 Phase III
C[C@H]1[C@@H](O)O[C@@H]2O[C@@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3

Basic Information

ChEMBL ID CHEMBL307261
Name ARTENIMOL
Phase Phase III
Structure Type MOL
InChI Key BJDCWCLMFKKGEE-ISOSDAIHSA-N
Therapeutic ✓ Yes

Known Names

.beta.-dihydroartemisinin Alaxin Artemether related compound a Artenimol Artenimol component of eurartesim dihydroartemisinin Artenimolum Cotecxin Cotexin Di-hydroqinghaosu Dihydroartemisinin Dihydroartemisinin, .beta.- Dihydroartemisinine +5 more
58
Targets
433
Activities
2
Assay Types
28
PK Parameters
20
Publications
17
Known Names
7
Indications
1
Mechanisms

Molecular Properties

284.4
MW (Da)
2.19
ALogP
5
HBA
1
HBD
57.1
PSA (Ų)
0.69
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem arte-
USAN Year 2024

Extended Properties

Molecular Formula C15H24O5
MW 284.35
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 3.88

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ferriprotoporphyrin IX binding agent BINDING AGENT Ferriprotoporphyrin IX

Indications

Malaria Fever Malaria, Falciparum Malaria, Vivax Carcinoma, Non-Small-Cell Lung Lupus Erythematosus, Systemic Polycystic Ovary Syndrome

ATC Classification

P01BE05
artenimol
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 397 meas. best 10.0
EC50 36 meas. best 9.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 10.0 8.7087 0.1 247
Plasmodium falciparum
CHEMBL364
EC50 9.85 8.4584 0.1 25
Unchecked
CHEMBL612545
IC50 9.66 5.76 0.2 10
CCRF-CEM
CHEMBL382
EC50 7.07 7.07 85.0 1
CCRF-CEM
CHEMBL382
IC50 7.05 6.1333 90.0 3
HL-60
CHEMBL383
IC50 6.75 5.5327 180.0 15
A549
CHEMBL392
IC50 6.64 4.8155 230.0 11
ADR5000 cell line
CHEMBL614266
EC50 6.58 6.58 265.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 6.57 4.7818 270.0 11
Cryptococcus neoformans
CHEMBL365
IC50 6.55 6.55 280.0 1
L02
CHEMBL4296457
IC50 6.44 4.98 360.0 4
SMMC-7721
CHEMBL613831
IC50 6.4 5.1567 400.0 3
HCT-15
CHEMBL612263
IC50 6.34 6.34 460.0 1
XF498
CHEMBL613533
IC50 6.27 6.27 540.0 1
786-0
CHEMBL613102
IC50 6.2 6.2 630.0 1
Jurkat
CHEMBL397
IC50 6.19 5.735 650.0 2
L6
CHEMBL614793
IC50 6.14 6.14 730.0 1
SK-MEL-2
CHEMBL614917
IC50 6.12 6.12 750.0 1
SK-OV-3
CHEMBL614925
IC50 6.07 6.07 850.0 1
Candida albicans
CHEMBL366
IC50 6.06 6.06 880.0 1
OVCAR-3
CHEMBL614213
IC50 6.0 5.03 1000.0 2
A2780
CHEMBL614004
IC50 6.0 6.0 1000.0 1
HUVEC
CHEMBL613979
IC50 5.85 5.45 1400.0 2
J774
CHEMBL614123
EC50 5.82 5.82 1500.0 2
MDA-MB-361
CHEMBL614129
EC50 5.77 5.77 1710.0 1
C-33-A
CHEMBL2366313
EC50 5.77 5.77 1710.0 1
ADR5000 cell line
CHEMBL614266
IC50 5.74 5.74 1840.0 1
PC-3
CHEMBL390
IC50 5.6 4.9233 2490.0 3
HeLa
CHEMBL399
IC50 5.58 5.315 2660.0 2
Leishmania donovani
CHEMBL367
IC50 5.39 4.4717 4100.0 6
T47D
CHEMBL614361
EC50 5.34 5.34 4600.0 1
NCI-H460
CHEMBL396
IC50 5.28 5.28 5290.0 1
HT-29
CHEMBL384
IC50 5.28 5.005 5290.0 2
MDA-MB-231
CHEMBL400
IC50 5.28 4.575 5290.0 8
MCF7
CHEMBL387
IC50 5.16 4.4943 6880.0 7
BV-2
CHEMBL614781
IC50 5.13 5.13 7400.0 1
MCF7
CHEMBL387
EC50 5.08 5.08 8240.0 1
THP-1
CHEMBL614245
IC50 5.04 5.04 9050.0 1
Prostaglandin E synthase 2
CHEMBL4411
IC50 5.02 5.02 9600.0 1
K562
CHEMBL385
IC50 5.01 4.71 9810.0 4
HEK293
CHEMBL614818
IC50 5.0 4.9 9900.0 2
HeLa
CHEMBL399
EC50 4.98 4.98 10460.0 1
MDA-MB-231
CHEMBL400
EC50 4.97 4.97 10690.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.89 4.89 12800.0 1
HCT-116
CHEMBL394
IC50 4.87 4.4567 13600.0 3
A-431
CHEMBL614069
IC50 4.8 4.585 15740.0 2
COLO 205
CHEMBL614561
IC50 4.8 4.585 15740.0 2
CNE
CHEMBL613824
IC50 4.74 4.74 18400.0 1
HEp-2
CHEMBL614735
IC50 4.74 4.74 18100.0 1
P388/ADR
CHEMBL614218
IC50 4.68 4.68 20670.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1946000.0 ng.hr.mL-1 Homo sapiens
AUC 1949.0 ng.hr.mL-1 Homo sapiens
CL 72.0 mL.min-1.kg-1 Mus musculus
CL 72.0 mL.min-1.kg-1 Rattus norvegicus
CL 72.0 mL.min-1.kg-1 Rattus norvegicus
CL 72.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 2454.72 nM Homo sapiens
F - % Mus musculus
F - % Rattus norvegicus
F 1.4 % Mus musculus
T1/2 17.19 hr -
T1/2 0.4333 hr Mus musculus
T1/2 0.4333 hr Rattus norvegicus
T1/2 0.4333 hr Rattus norvegicus
T1/2 720.0 hr Homo sapiens
T1/2 720.0 hr Homo sapiens
T1/2 0.85 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Rattus norvegicus
T1/2 17.0 hr -
T1/2 0.3833 hr Rattus norvegicus
T1/2 17.0 hr -
T1/2 0.5 hr Rattus norvegicus
Tmax 2.8 hr Homo sapiens
Vd 3.0 L.kg-1 Mus musculus
Vd 3.0 L.kg-1 Rattus norvegicus
Vd 3.0 L.kg-1 Rattus norvegicus
Vd 1.47 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 26651537
Plasmodium falciparum IC50 = 0.11 nM 9.96 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 28001067
Plasmodium falciparum IC50 = 0.11 nM 9.96 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 32067457
Plasmodium falciparum EC50 = 0.14 nM 9.85 Antimalarial activity against blood stage Plasmodium falciparum 3D7 assessed as ... 36736152
Plasmodium falciparum IC50 = 0.146 nM 9.84 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 ... 26651537
Plasmodium falciparum IC50 = 0.15 nM 9.82 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 28001067
Plasmodium falciparum IC50 = 0.15 nM 9.82 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 as... 32067457
Unchecked IC50 = 0.22 nM 9.66 Evaluated for the neurotoxicity against NB2a Neuroblastoma cells. 10893313
Plasmodium falciparum IC50 = 0.3 nM 9.52 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum C6ha... 19188388
Plasmodium falciparum IC50 = 0.3 nM 9.52 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 af... 29236492
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against synchronous ring stage of Plasmodium falciparum 3D... 34058708
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against Plasmodium falciparum IMT 10354 assessed as inhibi... 20547801
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against Plasmodium falciparum IMT 10354 harboring Ppcrt M7... 20547801
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 af... 29236492
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antiplasmodial activity against drug-sensitive Plasmodium falciparum 3D7 ring st... 29969262
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against Plasmodium falciparum Dd2 after 72 hrs by DAPI sta... 30537832
Plasmodium falciparum IC50 = 0.41 nM 9.39 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum W2 by... 20065051
Plasmodium falciparum IC50 = 0.43 nM 9.37 Antiplasmodial activity against 4-aminoquinoline/antifolates-resistant Plasmodiu... 29969262
Plasmodium falciparum IC50 = 0.45 nM 9.35 Antiplasmodial activity against Plasmodium falciparum W2 assessed as inhibition ... 34213340
Plasmodium falciparum IC50 = 0.49 nM 9.31 Antimicrobial activity against chloroquine-resistant Plasmodium falciparum K1 by... 20065051

Literature References

PubMed DOI Target Context # Activities
20547801 10.1128/aac.00183-10 Plasmodium falciparum 46
34847494 10.1016/j.bmc.2021.116520 Mus musculus 38
19188388 10.1128/aac.01656-08 Plasmodium falciparum 22
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
20566762 10.1128/aac.00121-10 Plasmodium falciparum 19
27371926 10.1016/j.ejmech.2016.06.035 NON-PROTEIN TARGET 18
22679214 10.1124/dmd.112.045765 Hepatocyte 18
27371926 10.1016/j.ejmech.2016.06.035 Molecular identity unknown 16
17227762 10.1074/jbc.m610375200 HL-60 16
33508479 10.1016/j.ejmech.2021.113193 Plasmodium falciparum 15
24684842 10.1016/j.bmcl.2014.03.010 Mycobacterium tuberculosis 11
28195463 10.1021/acs.jmedchem.6b01733 Plasmodium yoelii 10
22575162 10.1016/j.bmc.2012.04.025 HL-60 10
33691167 10.1016/j.bmcl.2021.127912 OVCAR-3 9
17404003 10.1128/aac.01479-06 Plasmodium falciparum 8
33541085 10.1021/acs.jmedchem.0c02104 Plasmodium falciparum 7
17116669 10.1128/aac.01023-06 Plasmodium falciparum 7
19528277 10.1128/aac.01717-08 Homo sapiens 7
19501507 10.1016/j.bmcl.2009.05.076 HL-60 6
19770282 10.1128/aac.00638-09 Plasmodium falciparum 6

Data from ChEMBL 36 via Core Engine