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Compound Detail

CHEMBL1450

ATOVAQUONE
💊 Approved Drug
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💊 Approved Drug
O=C1C(O)=C([C@H]2CC[C@H](c3ccc(Cl)cc3)CC2)C(=O)c2ccccc21

Basic Information

ChEMBL ID CHEMBL1450
Name ATOVAQUONE
Phase Approved
Structure Type MOL
InChI Key KUCQYCKVKVOKAY-CTYIDZIISA-N
Therapeutic ✓ Yes

Known Names

566C 566C80 Atovacuona Atovaquone Atovaquone component of malarone Atovaquone component of malarone pediatric Mepron NSC-759582 Wellvone
18
Targets
221
Activities
3
Assay Types
11
PK Parameters
20
Publications
9
Known Names
11
Indications
1
Mechanisms

Molecular Properties

366.8
MW (Da)
5.51
ALogP
3
HBA
1
HBD
54.4
PSA (Ų)
0.76
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1993

Extended Properties

Molecular Formula C22H19ClO3
MW 366.84
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.20

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome b inhibitor INHIBITOR Cytochrome b

Indications

Amebiasis Malaria Pneumocystis Infections Pneumonia, Pneumocystis Malaria, Falciparum Infections Severe Acute Respiratory Syndrome Toxoplasmosis, Cerebral Carcinoma, Non-Small-Cell Lung Gastroesophageal Reflux Leukemia, Myeloid, Acute

ATC Classification

P01AX06
atovaquone
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 177 meas. best 10.85
EC50 41 meas. best 10.0
Ki 3 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium berghei
CHEMBL612653
IC50 10.85 8.8877 0.0 13
Plasmodium falciparum
CHEMBL364
EC50 10.0 7.9929 0.1 31
Plasmodium falciparum
CHEMBL364
IC50 10.0 8.4698 0.1 127
NON-PROTEIN TARGET
CHEMBL3879801
EC50 10.0 10.0 0.1 1
Unchecked
CHEMBL612545
IC50 9.52 7.1793 0.3 15
Plasmodium berghei
CHEMBL612653
EC50 9.3 8.6167 0.5 3
Toxoplasma gondii
CHEMBL612888
IC50 8.62 7.414 2.4 5
Unchecked
CHEMBL612545
EC50 8.52 8.52 3.0 1
Plasmodium yoelii
CHEMBL612889
IC50 8.05 8.05 9.0 1
Unchecked
CHEMBL612545
Ki 8.05 6.31 9.0 2
Toxoplasma gondii
CHEMBL612888
EC50 7.5 7.5 32.0 1
Plasmodium yoelii yoelii
CHEMBL612328
IC50 7.24 7.24 57.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 6.64 6.64 230.0 1
HFF
CHEMBL614071
IC50 6.55 6.55 280.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL4523950
IC50 6.37 6.37 430.0 2
Monkeypox virus
CHEMBL613120
EC50 6.28 6.28 520.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2383
IC50 6.16 6.16 700.0 1
MCF7
CHEMBL387
IC50 6.0 6.0 1000.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
IC50 5.58 5.2075 2600.0 4
HepG2
CHEMBL395
IC50 5.07 4.7767 8496.0 3
Dihydroorotate dehydrogenase
CHEMBL3486
Ki 4.57 4.57 27000.0 1
J774
CHEMBL614123
EC50 4.55 4.55 28000.0 2
DU-145
CHEMBL613508
IC50 4.53 4.53 29300.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.15 mL.min-1.kg-1 Homo sapiens
CL 0.15 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.15 mL.min-1.kg-1 Homo sapiens
F 49.0 % Homo sapiens
F 23.0 % Homo sapiens
Fu 0.001 - Homo sapiens
Fu 0.001 - Homo sapiens
Ka 2.0 10'6/M Homo sapiens
MRT 67.0 hr Homo sapiens
T1/2 63.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium berghei IC50 = 0.014 nM 10.85 Antiplasmodial activity against exo-erythrocytic stage of GFP-Luc-fused Plasmodi... 30245402
NON-PROTEIN TARGET EC50 = 0.1 nM 10.0 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 MRA-... 24720377
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antiplasmodial activity against asexual blood stage of multidrug-resistant Plasm... 34111350
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antiplasmodial activity against asexual stage of chloroquine-sensitive Plasmodiu... 34111350
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antimalarial activity against multidrug resistant Plasmodium falciparum D6 infec... 32390431
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antimalarial activity against multidrug resistant Plasmodium falciparum Dd2 infe... 32390431
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 inf... 30852885
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum EC50 = 0.1 nM 10.0 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 MRA... 24720377
Plasmodium berghei IC50 = 0.16 nM 9.8 Antimalarial activity against exo-erythrocytic form of Plasmodium berghei infect... 24904967
Plasmodium falciparum EC50 = 0.19 nM 9.72 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 26295174
Plasmodium falciparum IC50 = 0.2 nM 9.7 Antimalarial activity against multidrug resistant Plasmodium falciparum 7G8 infe... 32390431
Plasmodium falciparum IC50 = 0.2 nM 9.7 Antimalarial activity against multidrug-resistant Plasmodium falciparum 7G8 infe... 30852885
Plasmodium falciparum IC50 = 0.2 nM 9.7 Antiplasmodial activity against asexual blood stage of multidrug-resistant Plasm... 34111350
Plasmodium berghei IC50 = 0.26 nM 9.59 Gametocytocidal activity against GFP-fused Plasmodium berghei liver stage gameto... 28653845
Plasmodium falciparum IC50 = 0.27 nM 9.57 Antimalarial activity against Plasmodium falciparum clinical isolates measured a... 32390431
Plasmodium falciparum IC50 = 0.27 nM 9.57 Antimalarial activity against Plasmodium falciparum 3D7 asexual forms incubated ... 31911292
Plasmodium falciparum IC50 = 0.27 nM 9.57 Antimalarial activity against Plasmodium falciparum 3D7A infected erythrocytes b... 18396855
Plasmodium falciparum IC50 = 0.28 nM 9.55 Antiplasmodial activity against Plasmodium falciparum W2 infected in human eryth... 22414614
Plasmodium falciparum IC50 = 0.3 nM 9.52 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 mea... 30613327

Literature References

PubMed DOI Target Context # Activities
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18212105 10.1128/aac.01203-07 Toxoplasma gondii 17
28635296 10.1021/acs.jmedchem.7b00621 Plasmodium falciparum 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
36812492 10.1021/acs.jmedchem.2c02092 Plasmodium falciparum 9
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 9
33636304 10.1016/j.bmcl.2021.127884 Plasmodium falciparum 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
34666274 10.1016/j.bmc.2021.116467 Toxoplasma gondii 7
24914738 10.1021/jm500535j Plasmodium falciparum 6
38290351 10.1016/j.ejmech.2024.116163 Plasmodium falciparum 6
25007124 10.1021/jm500715u Plasmodium falciparum 6
- 10.1039/C1MD00022E Plasmodium falciparum 6
32390431 10.1021/acs.jmedchem.0c00539 Plasmodium falciparum 5
31938463 10.1021/acsmedchemlett.9b00457 Plasmodium falciparum 5
22364417 10.1021/jm201184h Plasmodium berghei 5
- 10.1039/C3MD00373F Albumin 5

Data from ChEMBL 36 via Core Engine