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Compound Detail

CHEMBL682

AMODIAQUINE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL682
Name AMODIAQUINE
Phase Approved
Structure Type MOL
InChI Key OVCDSSHSILBFBN-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amodiaquin Amodiaquina Amodiaquine Amodiaquinum GNF-Pf-5648 NSC-13453 SJ000110703 Sunoquine
12
Targets
35
Activities
2
Assay Types
10
PK Parameters
20
Publications
8
Known Names
6
Indications

Molecular Properties

355.9
MW (Da)
5.18
ALogP
4
HBA
2
HBD
48.4
PSA (Ų)
0.60
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C20H22ClN3O
MW 355.87
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.16

Indications

Malaria Fever Malaria, Falciparum Malaria, Vivax Pregnancy Severe Acute Respiratory Syndrome

ATC Classification

P01BA06
amodiaquine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 24 meas. best 8.4
EC50 11 meas. best 8.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.4 7.7443 4.0 7
Plasmodium falciparum
CHEMBL364
 EC50 8.23 8.07 5.8 2
Cytochrome P450 2D6
CHEMBL289
 IC50 6.19 6.19 640.0 1
Cytochrome P450 2J2
CHEMBL3491
 IC50 6.0 6.0 990.0 1
dengue virus type 2
CHEMBL613966
 EC50 5.97 5.55 1080.0 2
dengue virus type 2
CHEMBL613966
 IC50 5.97 5.97 1080.0 1
Zika virus
CHEMBL4296612
 EC50 5.55 5.55 2800.0 2
Amyloid-beta precursor protein
CHEMBL2487
 IC50 5.4 5.335 4000.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 5.39 5.3567 4070.0 3
Hemozoin
CHEMBL613898
 IC50 5.07 4.92 8600.0 5
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
 EC50 4.7 4.412 20000.0 5
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.39 4.39 41000.0 1
No relevant target
CHEMBL2362975
 IC50 4.36 4.36 43500.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.11 4.11 77760.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 32.36 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 mL.min-1.g-1 Homo sapiens
CL 2.1e-05 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 0.021 uL/min Homo sapiens
CL 0.608 mL.min-1.g-1 Homo sapiens
CL 0.224 mL.min-1.g-1 Homo sapiens
CL 0.829 mL.min-1.g-1 Homo sapiens
CL 431.0 mL.min-1.g-1 Homo sapiens
T1/2 0.09 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 4.0 nM 8.4 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54... 26264839
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antiplasmodial activity against Plasmodium falciparum W2 infected in human eryth... 26264839
Plasmodium falciparum EC50 = 5.85 nM 8.23 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 26295174
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antimalarial activity against chloroquine-resistant and mefloquine-sensitive Pla... 30737133
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i... 27744189
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i... 27744189
Plasmodium falciparum IC50 = 8.0 nM 8.1 Antiplasmodial activity against multidrug-resistant Plasmodium falciparum K1 inf... 26264839
Plasmodium falciparum EC50 = 12.3 nM 7.91 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 26295174
Cytochrome P450 2D6 IC50 = 640.0 nM 6.19 Inhibition of CYP2D6 in human liver microsomes using bufuralol substrate by LC-M... 23033255
Cytochrome P450 2J2 IC50 = 990.0 nM 6.0 Inhibition of human recombinant CYP2J2 assessed as reduction in astemizole O-dem... 23033255
dengue virus type 2 EC50 = 1080.0 nM 5.97 Antiviral activity against Dengue virus 2 infected in BHK21 cells assessed after... 26771861
dengue virus type 2 IC50 = 1080.0 nM 5.97 Antiviral activity against DENV2 infected in BHK-21 cells assessed as viral repl... 31128447
Zika virus EC50 = 2800.0 nM 5.55 Antiviral activity against Zika virus PLCal_ZV infected in human Neural progenit... 31549836
Zika virus EC50 = 2800.0 nM 5.55 Antiviral activity against Zika virus PLCal_ZV infected in African green monkey ... 31549836
Amyloid-beta precursor protein IC50 = 4000.0 nM 5.4 Modulation of human wild-type APP695 expressed in SH-SY5Y cells assessed as inhi... 29559198
SARS-CoV-2 IC50 = 4070.0 nM 5.39 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 4070.0 nM 5.39 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 5150.0 nM 5.29 Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in ... -
Amyloid-beta precursor protein IC50 = 5400.0 nM 5.27 Modulation of human wild-type APP695 expressed in SH-SY5Y cells assessed as inhi... 29559198
dengue virus type 2 EC50 = 7410.0 nM 5.13 Antiviral activity against Dengue virus 2 infected in BHK21 cells assessed as re... 26771861

Literature References

PubMed DOI Target Context # Activities
33289551 10.1021/acs.jmedchem.0c00894 Nuclear receptor subfamily 4 group A member 2 24
33289551 10.1021/acs.jmedchem.0c00894 Nuclear receptor subfamily 4 group A member 3 12
33289551 10.1021/acs.jmedchem.0c00894 Nuclear receptor subfamily 4immunitygroup A member 1 12
31097988 10.1021/acsmedchemlett.8b00496 Plasmodium berghei 9
22942316 10.1124/dmd.112.047373 Liver microsome 6
26264839 10.1016/j.bmc.2015.07.051 Plasmodium berghei 6
25148516 10.1021/jm500942v Plasmodium berghei 5
26264839 10.1016/j.bmc.2015.07.051 Plasmodium falciparum 5
27394399 10.1016/j.ejmech.2016.06.033 Plasmodium berghei 5
29559198 10.1016/j.bmc.2018.03.016 Amyloid-beta precursor protein 4
27744189 10.1016/j.ejmech.2016.09.073 Plasmodium berghei 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.1101/2020.04.13.039917 SARS-CoV-2 3
31995375 10.1021/acs.jmedchem.0c00046 Albumin 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
23378628 10.1124/dmd.112.050054 ADMET 3
33629841 10.1021/acs.jmedchem.0c01779 Nuclear receptor subfamily 4 group A member 2 3
21467212 10.1124/dmd.111.039180 Liver microsome 3
22942316 10.1124/dmd.112.047373 Cytochrome P450 2C8 3
38909569 10.1016/j.ejmech.2024.116599 Plasmodium berghei 2

Data from ChEMBL 36 via Core Engine