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Compound Detail

CHEMBL411329

(R,S)-MEFLOQUINE
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O[C@H](c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)[C@@H]1CCCCN1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL411329
Name (R,S)-MEFLOQUINE
Phase Preclinical
Structure Type MOL
InChI Key XEEQGYMUWCZPDN-SWLSCSKDSA-N
7
Targets
14
Activities
3
Assay Types
3
PK Parameters
14
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

Ki 8 meas. best 7.21
IC50 5 meas. best 4.92
EC50 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL251
 Ki 7.21 7.21 61.0 3
Adenosine receptor A1
CHEMBL226
 Ki 6.61 6.5967 244.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.57 5.57 2700.0 1
Adenosine receptor A3
CHEMBL256
 Ki 5.16 5.16 6941.0 1
Adenosine receptor A2b
CHEMBL255
 Ki 5.15 5.15 7072.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.92 4.59 12000.0 4
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.87 4.87 13600.0 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

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a Ki = 61.0 nM 7.21 Binding affinity to human adenosine A2A receptor 18406614
Adenosine receptor A2a Ki = 61.0 nM 7.21 Inhibition of human recombinant adenosine receptor A2a 24164628
Adenosine receptor A2a Ki = 61.0 nM 7.21 Antagonist activity at human adenosine A2A receptor 35462165
Adenosine receptor A1 Ki = 244.0 nM 6.61 Inhibition of human recombinant adenosine A1 receptor 24164628
Adenosine receptor A1 Ki = 255.0 nM 6.59 Binding affinity to human adenosine A1 receptor 18406614
Adenosine receptor A1 Ki = 255.0 nM 6.59 Antagonist activity at human adenosine A1 receptor 35462165
NON-PROTEIN TARGET EC50 = 2700.0 nM 5.57 Antiviral activity against JC polyomavirus M1/SVEdelta infected in human SVG-A c... 19258267
Adenosine receptor A3 Ki = 6941.0 nM 5.16 Inhibition of human recombinant adenosine A3 receptor 24164628
Adenosine receptor A2b Ki = 7072.0 nM 5.15 Inhibition of human recombinant adenosine receptor A2b 24164628
Cytochrome P450 3A4 IC50 = 12000.0 nM 4.92 Inhibition of CYP3A4 in human liver microsomes assessed as reduction in 6-beta-h... 34782182
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 13600.0 nM 4.87 Inhibition of hERG channel expressed in CHO cells at holding potential of -80 mV... 34782182
Cytochrome P450 3A4 IC50 = 19000.0 nM 4.72 Inhibition of CYP3A4 in human liver microsomes assessed as reduction in 6-beta-h... 34782182
Cytochrome P450 3A4 IC50 = 43000.0 nM 4.37 Inhibition of CYP3A4 in human liver microsomes assessed as reduction in 1'-hydro... 34782182
Cytochrome P450 3A4 IC50 = 45000.0 nM 4.35 Inhibition of CYP3A4 in human liver microsomes assessed as reduction in 1'-hydro... 34782182

Literature References

PubMed DOI Target Context # Activities
34782182 10.1016/j.ejmech.2021.113981 ADMET 6
34782182 10.1016/j.ejmech.2021.113981 Cytochrome P450 3A4 4
18406614 10.1016/j.bmcl.2008.03.075 Adenosine receptor A2a 1
18406614 10.1016/j.bmcl.2008.03.075 Adenosine receptor A1 1
19258267 10.1128/aac.01614-08 NON-PROTEIN TARGET 1
24164628 10.1021/jm4011669 Unchecked 1
24164628 10.1021/jm4011669 Adenosine receptor A2b 1
24164628 10.1021/jm4011669 Adenosine receptor A2a 1
24164628 10.1021/jm4011669 Adenosine receptor A1 1
24164628 10.1021/jm4011669 Adenosine receptor A3 1
- 10.6019/CHEMBL3301361 ADMET 1
35462165 10.1016/j.ejmech.2022.114378 Adenosine receptor A2a 1
35462165 10.1016/j.ejmech.2022.114378 Adenosine receptor A1 1
34782182 10.1016/j.ejmech.2021.113981 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine