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Compound Detail

CHEMBL2058833

GANAPLACIDE
🧪 Phase II
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🧪 Phase II
CC1(C)c2nc(-c3ccc(F)cc3)c(Nc3ccc(F)cc3)n2CCN1C(=O)CN
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2058833
Name GANAPLACIDE
Phase Phase II
Structure Type MOL
InChI Key BUPRVECGWBHCQV-UHFFFAOYSA-N

Known Names

Ganaplacida Ganaplacide GNF 156 GNF-156 KAF 156 KAF-156 Kaf156
5
Targets
23
Activities
3
Assay Types
30
PK Parameters
20
Publications
7
Known Names
2
Indications

Molecular Properties

411.5
MW (Da)
3.61
ALogP
5
HBA
2
HBD
76.2
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Extended Properties

Molecular Formula C22H23F2N5O
MW 411.46
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.00

Indications

Malaria Malaria, Falciparum

Activity Summary

IC50 12 meas. best 8.06
EC50 10 meas. best 8.26
Ki 1 meas. best 6.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium vivax
CHEMBL613013
 EC50 8.26 8.26 5.5 1
Plasmodium falciparum
CHEMBL364
 EC50 8.22 7.5278 6.0 9
Unchecked
CHEMBL612545
 IC50 8.06 7.5044 8.8 9
Plasmodium falciparum
CHEMBL364
 IC50 7.8 7.8 16.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 6.81 6.81 156.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.87 4.87 13400.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 5003.35 ng.hr.mL-1 Mus musculus
AUC 1694.8 ng.hr.mL-1 Mus musculus
AUC 200.38 ng.hr.mL-1 Rattus norvegicus
AUC 753.38 ng.hr.mL-1 Rattus norvegicus
AUC 400.76 ng.hr.mL-1 Rattus norvegicus
AUC 3018.88 ng.hr.mL-1 Rattus norvegicus
AUC 14351.72 ng.hr.mL-1 Rattus norvegicus
AUC 83000000.0 ng.hr.mL-1 Homo sapiens
CL 49.2 mL.min-1.kg-1 Mus musculus
CL 67.5 mL.min-1.kg-1 Rattus norvegicus
CL 90.0 mL.min-1.kg-1 Rattus norvegicus
CL 37.8 mL.min-1.kg-1 Mus musculus
CL 548.0 mL.min-1.kg-1 Mus musculus
Cmax 1538.0 nM Mus musculus
Cmax 126.0 nM Rattus norvegicus
Cmax 91.0 nM Rattus norvegicus
Cmax 580.0 nM Rattus norvegicus
Cmax 34885.0 nM Rattus norvegicus
Cmax 337.82 nM Rattus norvegicus
Cmax 18.47 nM Homo sapiens
F 74.0 % Mus musculus
F 20.0 % Rattus norvegicus
F 40.0 % Rattus norvegicus
F 57.0 % Rattus norvegicus
F 48.0 % Rattus norvegicus
F 74.0 % Mus musculus
T1/2 4.35 hr Mus musculus
T1/2 2.0 hr Mus musculus
T1/2 4.6 hr Rattus norvegicus
T1/2 4.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium vivax EC50 = 5.5 nM 8.26 Antimalarial activity against Plasmodium vivax assessed as reduction in parasite... 31385706
Plasmodium falciparum EC50 = 6.0 nM 8.22 Antimalarial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gree... 22524250
Plasmodium falciparum EC50 = 6.0 nM 8.22 Antimalarial activity against Plasmodium falciparum W2 33131885
Plasmodium falciparum EC50 = 8.0 nM 8.1 Antimalarial activity against Plasmodium falciparum Dd2 assessed as reduction in... 38554474
Unchecked IC50 = 8.8 nM 8.06 Binding affinity to wild type CARL in multidrug-resistant Plasmodium falciparum ... 33573376
Plasmodium falciparum EC50 = 10.0 nM 8.0 Antimalarial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR gre... 22524250
Plasmodium falciparum EC50 = 10.0 nM 8.0 Antimalarial activity against Plasmodium falciparum 3D7 33131885
Unchecked IC50 = 11.1 nM 7.96 Binding affinity to CARL V1053G mutant in multidrug-resistant Plasmodium falcipa... 33573376
Plasmodium falciparum EC50 = 12.6 nM 7.9 Antimalarial activity against Plasmodium falciparum assessed as reduction in par... 31385706
Unchecked IC50 = 12.6 nM 7.9 Binding affinity to CARL L1073Q mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 14.8 nM 7.83 Binding affinity to CARL A1122E mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 14.8 nM 7.83 Binding affinity to CARL M1050I mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 15.2 nM 7.82 Binding affinity to CARL 11072V mutant in multidrug-resistant Plasmodium falcipa... 33573376
Plasmodium falciparum IC50 = 16.0 nM 7.8 Antiplasmodial activity against multidrug-sensitive Plasmodium falciparum NF54 t... 33573376
Unchecked IC50 = 16.4 nM 7.79 Binding affinity to CARL L1108W mutant in multidrug-resistant Plasmodium falcipa... 33573376
Plasmodium falciparum EC50 = 17.0 nM 7.77 Antiplasmodial activity against Plasmodium falciparum Dd2 infected in erythrocyt... 39024967
Unchecked IC50 = 108.4 nM 6.96 Binding affinity to CARL E1104K mutant in multidrug-resistant Plasmodium falcipa... 33573376
Cytochrome P450 3A4 Ki = 156.0 nM 6.81 Inhibition of CYP3A4 (unknown origin) 31385706
Plasmodium falciparum EC50 = 1530.0 nM 5.82 Antimalarial activity against KAF-156 resistant Plasmodium falciparum Dd2 harbor... 38554474
Plasmodium falciparum EC50 = 1920.0 nM 5.72 Antiplasmodial activity against multidrug-resistant Plasmodium falciparum Dd2 ha... 39024967

Literature References

PubMed DOI Target Context # Activities
22524250 10.1021/jm300041e Rattus norvegicus 22
33573376 10.1021/acs.jmedchem.1c00034 Unchecked 18
31385706 10.1021/acs.jmedchem.9b00761 ADMET 17
22524250 10.1021/jm300041e Mus musculus 9
22524250 10.1021/jm300041e Plasmodium berghei 7
22524250 10.1021/jm300041e Unchecked 6
33573376 10.1021/acs.jmedchem.1c00034 ADMET 6
31385706 10.1021/acs.jmedchem.9b00761 Plasmodium vivax 3
31385706 10.1021/acs.jmedchem.9b00761 Plasmodium falciparum 3
22524250 10.1021/jm300041e Plasmodium falciparum 2
38554474 10.1016/j.ejmech.2024.116354 Plasmodium falciparum 2
33131885 10.1016/j.ejmech.2020.112955 Plasmodium falciparum 2
39024967 10.1016/j.ejmech.2024.116677 Plasmodium falciparum 2
22524250 10.1021/jm300041e Liver microsomes 2
22524250 10.1021/jm300041e ADMET 2
22524250 10.1021/jm300041e Caco-2 2
22524250 10.1021/jm300041e Cytochrome P450 2C19 1
22524250 10.1021/jm300041e Cytochrome P450 2C9 1
22524250 10.1021/jm300041e Cytochrome P450 2D6 1
22524250 10.1021/jm300041e Cytochrome P450 3A4 1

Data from ChEMBL 36 via Core Engine