Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL172

(S,R)-MEFLOQUINE
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
O[C@@H](c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)[C@H]1CCCCN1

Basic Information

ChEMBL ID CHEMBL172
Name (S,R)-MEFLOQUINE
Phase Preclinical
Structure Type MOL
InChI Key XEEQGYMUWCZPDN-DOMZBBRYSA-N
22
Targets
109
Activities
3
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

378.3
MW (Da)
4.45
ALogP
3
HBA
2
HBD
45.1
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H16F6N2O
MW 378.32
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.03

Activity Summary

IC50 95 meas. best 9.4
EC50 11 meas. best 8.6
Ki 3 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.4 7.5212 0.4 67
Plasmodium falciparum
CHEMBL364
EC50 8.6 7.982 2.5 5
Plasmodium knowlesi
CHEMBL613011
IC50 7.4 7.4 40.0 1
Plasmodium vivax
CHEMBL613013
IC50 7.36 7.36 44.0 1
Unchecked
CHEMBL612545
IC50 6.4 5.6467 400.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 6.28 6.28 530.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 6.18 4.93 667.0 5
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 5.72 5.72 1900.0 1
Leishmania donovani
CHEMBL367
IC50 5.62 5.015 2410.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.58 5.2 2600.0 2
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.49 5.315 3250.0 2
dengue virus type 2
CHEMBL613966
EC50 5.49 5.49 3220.0 1
Zika virus
CHEMBL4296612
EC50 5.44 5.42 3600.0 2
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.35 5.35 4500.0 1
Trypanosoma cruzi
CHEMBL368
IC50 5.35 5.35 4480.0 1
L6
CHEMBL614793
IC50 5.35 5.35 4500.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.18 5.18 6553.0 1
ADMET
CHEMBL612558
IC50 5.02 5.02 9500.0 1
HepG2
CHEMBL395
EC50 5.01 5.01 9800.0 1
U-251
CHEMBL615022
IC50 5.0 5.0 10000.0 1
HepG2
CHEMBL395
IC50 4.94 4.94 11500.0 1
Adenosine receptor A1
CHEMBL226
Ki 4.85 4.85 14044.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 4.83 4.83 14900.0 1
Unchecked
CHEMBL612545
EC50 4.82 4.82 15000.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.75 4.75 18000.0 1
Heme
CHEMBL4651321
IC50 4.33 4.33 47000.0 1
Hemozoin
CHEMBL613898
IC50 4.22 4.22 60000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 20.0 mL.min-1.g-1 Mus musculus
CL 20.0 mL.min-1.g-1 Rattus norvegicus
CL 20.0 mL.min-1.g-1 Homo sapiens
Cmax 132.16 nM Homo sapiens
Fu 3.2 ng/g Mus musculus
T1/2 336.0 hr Homo sapiens
T1/2 1.0 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 23.0 hr Mus musculus
T1/2 6.2 hr Plasmodium falciparum
T1/2 480.0 hr Homo sapiens
Tmax 0.08333 hr Mus musculus
Vd 20.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 inf... 24900369
Plasmodium falciparum IC50 = 2.4 nM 8.62 DNDI: Malaria in Vitro, 72 hour -
Plasmodium falciparum EC50 = 2.5 nM 8.6 Antiplasmodium activity against Plasmodium falciparum W2 by flow cytometry 26617969
Plasmodium falciparum IC50 = 4.93 nM 8.31 Antimalarial activity against CQ-resistant, MFQ-susceptible Plasmodium falciparu... 24742203
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 aft... 26640981
Plasmodium falciparum IC50 = 6.1 nM 8.21 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 inf... 30715882
Plasmodium falciparum IC50 = 6.5 nM 8.19 Antispasmodial activity against chloroquine-sensitive asexual blood stages of Pl... 28653845
Plasmodium falciparum IC50 = 6.5 nM 8.19 Antiplasmodial activity against Plasmodium falciparum 3D7 asexual blood stages a... 25195945
Plasmodium falciparum IC50 = 6.6 nM 8.18 Antispasmodial activity against multidrug-resistant asexual blood stages of Plas... 28653845
Plasmodium falciparum IC50 = 6.6 nM 8.18 Antiplasmodial activity against Plasmodium falciparum Dd2 asexual blood stages a... 25195945
Plasmodium falciparum EC50 = 7.0 nM 8.15 Antiplasmodial activity against erythrocytic stage of multidrug-resistant Plasmo... 23587422
Plasmodium falciparum IC50 = 7.0 nM 8.15 Antimalarial activity against chloroquine-resistant/mefloquine-sensitive Plasmod... 25488841
Plasmodium falciparum IC50 = 7.2 nM 8.14 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 23489135
Plasmodium falciparum IC50 = 8.4 nM 8.08 Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 24568587
Plasmodium falciparum IC50 = 9.1 nM 8.04 Antimalarial activity against chloroquine/mefloquine-sensitive Plasmodium falcip... 27544402
Plasmodium falciparum IC50 = 9.4 nM 8.03 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 ass... -
Plasmodium falciparum IC50 = 12.0 nM 7.92 Antimalarial activity against Plasmodium falciparum 3D7 assessed as reduction in... 34058708
Plasmodium falciparum IC50 = 12.0 nM 7.92 Antimalarial activity against drug-sensitive Plasmodium falciparum NF54 24568587
Plasmodium falciparum EC50 = 13.0 nM 7.89 Antiplasmodial activity against ring-stage Plasmodium falciparum 3D7 assessed as... 29800827
Plasmodium falciparum IC50 = 13.0 nM 7.89 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885

Literature References

PubMed DOI Target Context # Activities
24742203 10.1021/jm500033r Plasmodium falciparum 8
33989911 10.1016/j.ejmech.2021.113408 Plasmodium falciparum 8
28052200 10.1021/acs.jmedchem.6b01586 Plasmodium berghei 7
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 6
34782182 10.1016/j.ejmech.2021.113981 ADMET 6
27544402 10.1016/j.bmcl.2016.08.005 Plasmodium falciparum 6
23489135 10.1021/jm400004u Plasmodium falciparum 5
30737133 10.1016/j.bmc.2019.01.044 Plasmodium berghei 4
34782182 10.1016/j.ejmech.2021.113981 Cytochrome P450 3A4 4
34782182 10.1016/j.ejmech.2021.113981 Plasmodium falciparum 4
24900369 10.1021/ml2002136 Plasmodium falciparum 4
22128829 10.1021/jm201214d Plasmodium berghei 4
30779564 10.1021/acs.jmedchem.8b01353 ADMET 4
28800458 10.1016/j.ejmech.2017.07.061 ADMET 3
23228469 10.1016/j.bmcl.2012.10.126 Plasmodium falciparum 3
25195945 10.1021/jm500811p Plasmodium falciparum 3
926111 10.1021/jm00219a002 Calf thymus DNA 3
23927763 10.1021/jm4004279 Plasmodium falciparum 3
28068604 10.1016/j.ejmech.2016.12.058 Zika virus 3
25488841 10.1016/j.bmcl.2014.11.039 Plasmodium falciparum 3

Data from ChEMBL 36 via Core Engine