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Compound Detail

CHEMBL361497

ARTESUNATE
💊 Approved Drug
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💊 Approved Drug
C[C@H]1[C@H](OC(=O)CCC(=O)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 CHEMBL361497
Name ARTESUNATE
Phase Approved
Structure Type MOL
InChI Key FIHJKUPKCHIPAT-AHIGJZGOSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL307261

Known Names

.alpha.-artesunic acid Arsumax Artesunate Artesunate amivas Artesunato Artesunatum Artesunic acid Dihydroqinghaosu hemisuccinate LJPC-0118 NSC-712571 Plasmotrin Qinghaozhi +2 more
43
Targets
351
Activities
2
Assay Types
10
PK Parameters
20
Publications
14
Known Names
17
Indications
1
Mechanisms

Molecular Properties

384.4
MW (Da)
2.60
ALogP
7
HBA
1
HBD
100.5
PSA (Ų)
0.58
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product Prodrug
USAN Stem arte-
USAN Year 2002

Extended Properties

Molecular Formula C19H28O8
MW 384.43
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness 3.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Malaria Cytomegalovirus Infections Fever Malaria, Falciparum Malaria, Vivax Schistosomiasis Schistosomiasis haematobia Severe Acute Respiratory Syndrome Colorectal Neoplasms Conjunctivitis, Allergic Crohn Disease Intestinal Neoplasms Breast Neoplasms Carcinoma, Hepatocellular Friedreich Ataxia Idiopathic Pulmonary Fibrosis Neoplasms

ATC Classification

P01BE03
artesunate
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 303 meas. best 9.52
EC50 48 meas. best 9.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.52 8.2735 0.3 203
Plasmodium vivax
CHEMBL613013
IC50 9.41 8.8957 0.4 14
Plasmodium falciparum
CHEMBL364
EC50 9.09 7.9729 0.8 31
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.94 6.3333 1.2 9
Plasmodium malariae
CHEMBL613257
IC50 8.75 8.65 1.8 2
CCRF-CEM
CHEMBL382
EC50 7.16 6.78 69.0 2
CCRF-CEM
CHEMBL382
IC50 7.16 6.1025 70.0 4
ADR5000 cell line
CHEMBL614266
EC50 7.0 6.6733 100.0 3
Toxoplasma gondii
CHEMBL612888
EC50 6.67 6.67 213.0 1
HCT-116
CHEMBL394
IC50 6.34 5.568 460.0 5
HeLa
CHEMBL399
IC50 6.3 5.295 500.0 6
HUVEC
CHEMBL613979
IC50 5.96 5.015 1092.0 2
ADR5000 cell line
CHEMBL614266
IC50 5.92 5.92 1200.0 1
L6
CHEMBL614793
IC50 5.82 5.2067 1500.0 3
Prostaglandin E synthase 2
CHEMBL4411
IC50 5.8 5.8 1600.0 1
C-33-A
CHEMBL2366313
EC50 5.74 5.74 1830.0 1
HL-60
CHEMBL383
IC50 5.7 5.7 2000.0 1
T47D
CHEMBL614361
EC50 5.65 5.65 2220.0 1
MDA-MB-361
CHEMBL614129
EC50 5.64 5.64 2270.0 1
Hepatitis B virus
CHEMBL613497
IC50 5.64 5.64 2300.0 1
HEK293
CHEMBL614818
IC50 5.54 5.2333 2900.0 3
Human betaherpesvirus 5
CHEMBL371
IC50 5.42 5.42 3800.0 1
MCF7
CHEMBL387
EC50 5.38 5.38 4210.0 1
T-cell
CHEMBL614309
IC50 5.34 5.34 4580.0 1
Schistosoma mansoni
CHEMBL612893
IC50 5.3 4.7067 4970.0 3
A549
CHEMBL392
IC50 5.27 4.7867 5400.0 3
Human betaherpesvirus 5
CHEMBL371
EC50 5.27 5.27 5410.0 4
K562
CHEMBL385
IC50 5.22 5.22 5999.0 1
HepG2
CHEMBL395
IC50 5.19 4.6378 6500.0 9
MRC5
CHEMBL614181
IC50 5.17 4.805 6800.0 2
Leukemia cell
CHEMBL614844
IC50 5.16 5.16 6887.0 1
Unchecked
CHEMBL612545
IC50 5.15 4.9967 7100.0 3
BT-474
CHEMBL614529
IC50 5.11 5.11 7800.0 1
WM 266-4
CHEMBL4296510
IC50 5.07 5.07 8460.0 1
Trypanosoma cruzi
CHEMBL368
IC50 5.03 4.96 9440.0 2
SK-HEP1
CHEMBL614912
IC50 5.0 5.0 10000.0 1
MDA-MB-231
CHEMBL400
EC50 5.0 5.0 10040.0 1
HeLa
CHEMBL399
EC50 4.92 4.92 12030.0 1
Leishmania donovani
CHEMBL367
IC50 4.92 4.92 12100.0 1
SARS-CoV-2
CHEMBL4303835
EC50 4.89 4.89 12980.0 1
Trypanosoma brucei brucei
CHEMBL612851
IC50 4.89 4.7567 12800.0 3
MCF-10A
CHEMBL614321
IC50 4.68 4.68 21000.0 1
MCF7
CHEMBL387
IC50 4.41 4.41 38710.0 1
MDA-MB-231
CHEMBL400
IC50 4.34 4.23 46000.0 2
OVCAR-3
CHEMBL614213
IC50 4.17 4.17 67300.0 1
L02
CHEMBL4296457
IC50 4.14 4.14 72170.0 1
SMMC-7721
CHEMBL613831
IC50 4.14 4.14 72300.0 1
J82
CHEMBL614586
IC50 4.12 4.12 75700.0 1
KB
CHEMBL398
IC50 4.11 4.11 78500.0 2
Lymphocyte
CHEMBL5314318
IC50 4.1 4.1 80000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 113.0 ng.hr.mL-1 Homo sapiens
AUC 1404.0 ng.hr.mL-1 Homo sapiens
CL 1070.0 mL.min-1.kg-1 Homo sapiens
Cmax 133.44 nM Homo sapiens
Cmax 1230.39 nM Homo sapiens
Fu 0.25 - Homo sapiens
MRT 0.32 hr Homo sapiens
T1/2 1.3 hr Homo sapiens
T1/2 0.22 hr Homo sapiens
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.3 nM 9.52 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 31961680
Plasmodium vivax IC50 = 0.39 nM 9.41 Antimalarial activity against trophozoites stage of Plasmodium vivax assessed as... 21135175
Plasmodium falciparum IC50 = 0.44 nM 9.36 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 as... 32067457
Plasmodium falciparum IC50 = 0.44 nM 9.36 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 28001067
Plasmodium falciparum IC50 = 0.443 nM 9.35 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 ... 26651537
Plasmodium falciparum IC50 = 0.48 nM 9.32 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 32067457
Plasmodium falciparum IC50 = 0.48 nM 9.32 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 28001067
Plasmodium falciparum IC50 = 0.5 nM 9.3 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 26651537
Plasmodium falciparum IC50 = 0.5 nM 9.3 Antiplasmodial activity against chloroquine and pyrimethamine resistant Plasmodi... 28988153
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in human eryt... 34437804
Plasmodium falciparum IC50 = 0.67 nM 9.17 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 32790306
Plasmodium falciparum IC50 = 0.67 nM 9.17 Antiplasmodial activity against 4-aminoquinoline/antifolates-resistant Plasmodiu... 29969262
Plasmodium falciparum IC50 = 0.68 nM 9.17 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 20876370
Plasmodium falciparum IC50 = 0.67 nM 9.17 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 ... 28400231
Plasmodium vivax IC50 = 0.74 nM 9.13 Antimalarial activity against Plasmodium vivax assessed as parasites growth inhi... 21135175
Plasmodium vivax IC50 = 0.75 nM 9.12 Antimalarial activity against ring stage of Plasmodium vivax assessed as parasit... 21135175
Plasmodium falciparum EC50 = 0.81 nM 9.09 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 37236020
Plasmodium falciparum IC50 = 0.82 nM 9.09 Antimalarial activity against Plasmodium falciparum 3D7 assessed as growth inhib... 24561670
Plasmodium vivax IC50 = 0.83 nM 9.08 Antimicrobial activity against Plasmodium vivax at the ring stage measured after... 18180357
Plasmodium vivax IC50 = 0.86 nM 9.07 Antimicrobial activity against Plasmodium vivax at the ring stage by microscopy 18180357

Literature References

PubMed DOI Target Context # Activities
20566762 10.1128/aac.00121-10 Plasmodium falciparum 19
20813948 10.1126/science.1193225 Plasmodium berghei 15
17242150 10.1128/aac.00967-06 Plasmodium vinckei petteri 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19908867 10.1021/jm901357n Plasmodium falciparum 11
16033274 10.1021/jm049040u Mus musculus 10
31938463 10.1021/acsmedchemlett.9b00457 Plasmodium falciparum 10
20350951 10.1128/aac.01526-09 Plasmodium berghei 9
33989911 10.1016/j.ejmech.2021.113408 Plasmodium falciparum 9
- 10.6019/CHEMBL5058564 U2OS 9
20568778 10.1021/jm100410f Plasmodium berghei 8
33508479 10.1016/j.ejmech.2021.113193 Plasmodium falciparum 8
- 10.6019/CHEMBL5058564 HEK-293T 8
- 10.6019/CHEMBL5058564 Fibroblast 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
25074847 10.1016/j.bmc.2014.07.007 NON-PROTEIN TARGET 7
23685181 10.1016/j.bmc.2013.04.059 SK-HEP1 7
25074847 10.1016/j.bmc.2014.07.007 Unchecked 7
34437804 10.1021/acs.jmedchem.1c00441 Plasmodium falciparum 7
34243044 10.1016/j.bmc.2021.116293 Candida albicans 7

Data from ChEMBL 36 via Core Engine