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Compound Detail

CHEMBL303933

PIPERAQUINE
🧪 Phase III
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🧪 Phase III
Clc1ccc2c(N3CCN(CCCN4CCN(c5ccnc6cc(Cl)ccc56)CC4)CC3)ccnc2c1

Basic Information

ChEMBL ID CHEMBL303933
Name PIPERAQUINE
Phase Phase III
Structure Type MOL
InChI Key UCRHFBCYFMIWHC-UHFFFAOYSA-N

Known Names

Piperaquine Piperaquinoline
5
Targets
128
Activities
3
Assay Types
30
PK Parameters
20
Publications
2
Known Names
4
Indications
1
Mechanisms

Molecular Properties

535.5
MW (Da)
5.42
ALogP
6
HBA
0
HBD
38.7
PSA (Ų)
0.33
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C29H32Cl2N6
MW 535.52
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -0.88

Mechanism of Action

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

Indications

Fever Malaria Malaria, Falciparum Malaria, Vivax

Activity Summary

IC50 126 meas. best 9.15
EC50 1 meas. best 7.9
Ki 1 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.15 7.5623 0.7 109
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.12 8.055 7.6 2
Plasmodium falciparum
CHEMBL364
EC50 7.9 7.9 12.5 1
Plasmodium vivax
CHEMBL613013
IC50 7.88 7.6885 13.2 13
Plasmodium malariae
CHEMBL613257
IC50 7.54 7.48 29.0 2
Cytochrome P450 3A4
CHEMBL340
Ki 7.05 7.05 90.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 46804.45 ng.hr.mL-1 Homo sapiens
AUC 40913.73 ng.hr.mL-1 Homo sapiens
AUC 33500.0 ng.hr.mL-1 Mus musculus
AUC 27300.0 ng.hr.mL-1 Mus musculus
AUC 19400.0 ng.hr.mL-1 Homo sapiens
AUC 7580.0 ng.hr.mL-1 Homo sapiens
AUC 8650.0 ng.hr.mL-1 Homo sapiens
AUC 20700.0 ng.hr.mL-1 Homo sapiens
AUC 8650.0 ng.hr.mL-1 Homo sapiens
AUC 9070.0 ng.hr.mL-1 Homo sapiens
AUC 19400.0 ng.hr.mL-1 Homo sapiens
AUC 25900.0 ng.hr.mL-1 Homo sapiens
AUC 44430.0 ng.hr.mL-1 Homo sapiens
AUC 56418.0 ng.hr.mL-1 Homo sapiens
CL 31.67 mL.min-1.kg-1 Mus musculus
CL 25.83 mL.min-1.kg-1 Mus musculus
Cmax 1060.65 nM Homo sapiens
T1/2 8.3 hr Homo sapiens
T1/2 413.0 hr Homo sapiens
T1/2 0.12 hr Homo sapiens
T1/2 9.3 hr Homo sapiens
T1/2 324.0 hr Homo sapiens
T1/2 487.2 hr Homo sapiens
T1/2 501.6 hr Homo sapiens
T1/2 280.8 hr Homo sapiens
T1/2 456.0 hr Homo sapiens
T1/2 427.2 hr Mus musculus
T1/2 386.4 hr Mus musculus
T1/2 14.16 hr Mus musculus
T1/2 496.8 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.7 nM 9.15 Antimalarial activity against CQ-sensitive Plasmodium falciparum D6 34655985
Plasmodium falciparum IC50 = 1.5 nM 8.82 Antimalarial activity against multidrug resistant Plasmodium falciparum Dd2 34655985
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antimicrobial activity against Plasmodium falciparum harboring mdr1 N86Y/D1246Y/... 20065051
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 21135175
Plasmodium falciparum IC50 = 3.4 nM 8.47 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 19188388
Plasmodium falciparum IC50 = 3.9 nM 8.41 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum C2 i... 19188388
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against drug-resistant Plasmodium falciparum 3D7 harboring... 30852885
Plasmodium falciparum IC50 = 5.9 nM 8.23 Antimalarial activity against Plasmodium falciparum clinical isolates measured a... 32390431
Plasmodium falciparum IC50 = 6.1 nM 8.21 Antimicrobial activity against Plasmodium falciparum by ELISA 20065051
Plasmodium falciparum IC50 = 6.26 nM 8.2 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum D6 by... 20065051
Plasmodium falciparum IC50 = 6.6 nM 8.18 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum C6ha... 19188388
Plasmodium falciparum IC50 = 7.1 nM 8.15 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 7.2 nM 8.14 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 30852885
Plasmodium falciparum IC50 = 7.4 nM 8.13 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
NON-PROTEIN TARGET IC50 = 7.57 nM 8.12 Antimalarial activity against Plasmodium ovale trophozoite stage infected in red... 20937779
Plasmodium falciparum IC50 = 8.1 nM 8.09 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D10 ... 19188388
Plasmodium falciparum IC50 = 8.3 nM 8.08 In vitro activity against Plasmodium falciparum D6 1597862
Plasmodium falciparum IC50 = 9.0 nM 8.05 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum IC50 = 9.1 nM 8.04 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum 7G8 ... 19188388
Plasmodium falciparum IC50 = 10.0 nM 8.0 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885

Literature References

PubMed DOI Target Context # Activities
20547801 10.1128/aac.00183-10 Plasmodium falciparum 46
18180343 10.1128/aac.00955-07 Homo sapiens 36
19188388 10.1128/aac.01656-08 Plasmodium falciparum 23
17967917 10.1128/aac.00555-07 Homo sapiens 22
17984231 10.1128/aac.00878-07 Mus musculus 19
17404003 10.1128/aac.01479-06 Plasmodium falciparum 16
19528277 10.1128/aac.01717-08 Plasmodium falciparum 7
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 6
19528277 10.1128/aac.01717-08 Homo sapiens 6
20065051 10.1128/aac.01412-09 Plasmodium falciparum 6
17984231 10.1128/aac.00878-07 Plasmodium berghei 5
19770282 10.1128/aac.00638-09 Plasmodium falciparum 5
21135175 10.1128/aac.01220-10 Plasmodium falciparum 5
18180357 10.1128/aac.01334-07 Plasmodium vivax 4
20876370 10.1128/aac.00801-10 Plasmodium vivax 4
21135175 10.1128/aac.01220-10 Plasmodium vivax 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
30715882 10.1021/acs.jmedchem.8b01799 Plasmodium falciparum 3
20876370 10.1128/aac.00801-10 Plasmodium falciparum 3
38290351 10.1016/j.ejmech.2024.116163 Plasmodium falciparum 2

Data from ChEMBL 36 via Core Engine