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Compound Detail

CHEMBL416956

MEFLOQUINE
💊 Approved Drug
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💊 Approved Drug
OC(c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)C1CCCCN1

Basic Information

ChEMBL ID CHEMBL416956
Name MEFLOQUINE
Phase Approved
Structure Type MOL
InChI Key XEEQGYMUWCZPDN-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

GNF-Pf-5544 Mefaquin Mefloquina Mefloquine NSC-758233 RO 21-5998 RO-215998 WR 142,490
18
Targets
236
Activities
2
Assay Types
4
PK Parameters
20
Publications
8
Known Names
9
Indications

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
First Approval 1989
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning
USAN Year 1975

Extended Properties

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

Indications

Malaria Malaria, Falciparum Schistosomiasis haematobia Pneumonia, Viral Respiratory Insufficiency Severe Acute Respiratory Syndrome Glioblastoma Gliosarcoma Leukoencephalopathy, Progressive Multifocal

ATC Classification

P01BC02
mefloquine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 217 meas. best 9.51
EC50 19 meas. best 8.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.51 7.7532 0.3 162
Plasmodium falciparum
CHEMBL364
EC50 8.31 7.5871 4.9 14
Plasmodium vivax
CHEMBL613013
IC50 8.19 7.8383 6.4 18
NON-PROTEIN TARGET
CHEMBL3879801
IC50 7.62 5.675 23.8 6
Plasmodium malariae
CHEMBL613257
IC50 7.43 7.38 36.8 2
Glycine receptor subunit alpha-1
CHEMBL5845
EC50 5.6 5.6 2500.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.58 5.335 2600.0 4
Unchecked
CHEMBL612545
IC50 5.54 4.795 2900.0 4
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.4 5.4 4000.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.36 5.36 4330.0 1
L6
CHEMBL614793
IC50 5.32 5.035 4760.0 4
Monkeypox virus
CHEMBL613120
EC50 5.29 5.29 5190.0 1
RAW264.7
CHEMBL612557
IC50 5.19 5.19 6500.0 1
Leishmania infantum
CHEMBL612848
IC50 5.16 5.16 7000.0 1
LoVo
CHEMBL614721
IC50 5.1 5.1 7900.0 1
MCF7
CHEMBL387
IC50 4.97 4.97 10600.0 1
Vero
CHEMBL391
IC50 4.96 4.96 11000.0 2
Protein kinase Pfmrk
CHEMBL4090
IC50 4.92 4.92 12000.0 1
Leishmania major
CHEMBL612879
EC50 4.9 4.88 12480.0 2
DU-145
CHEMBL613508
IC50 4.84 4.84 14400.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.1 10^5/M -
Ka 8.7 10^5/M Homo sapiens
Ka 8.0 10^4/M Homo sapiens
T1/2 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.31 nM 9.51 Intrinsic equimolar activity against Plasmodium falciparum D6 (Sierra Leone) rel... 3279208
Plasmodium falciparum IC50 = 0.7 nM 9.15 Antimalarial activity against Plasmodium falciparum W2 in MSF assay 18023189
Plasmodium falciparum IC50 = 1.11 nM 8.96 Intrinsic equimolar activity against Plasmodium falciparum W2 Indochina relative... 3279208
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum PFB ... 11170658
Plasmodium falciparum IC50 = 2.1 nM 8.68 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 20349996
Plasmodium falciparum IC50 = 2.1 nM 8.68 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by fi... 20547797
Plasmodium falciparum IC50 = 2.33 nM 8.63 Antimalarial activity against chloroquine-resistant, mefloquine-sensitive Plasmo... 18550377
Plasmodium falciparum IC50 = 3.09 nM 8.51 Antimalarial activity against Plasmodium falciparum W2 17887664
Plasmodium falciparum IC50 = 3.1 nM 8.51 Antimalarial activity against Plasmodium falciparum W2 16789736
Plasmodium falciparum IC50 = 3.09 nM 8.51 Antimalarial activity against chloroquine and pyrimethamine-resistant Plasmodium... 18550377
Plasmodium falciparum IC50 = 3.2 nM 8.49 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 inf... 20349996
Plasmodium falciparum IC50 = 4.6 nM 8.34 Antimicrobial activity against Plasmodium falciparum trophozoites by microscopy ... 18180357
Plasmodium falciparum IC50 = 4.8 nM 8.32 Antimalarial activity against Plasmodium falciparum W2 after 24 hrs by [3H]hypox... 11975516
Plasmodium falciparum IC50 = 4.93 nM 8.31 Antimalarial activity against Plasmodium falciparum W2 21265542
Plasmodium falciparum IC50 = 4.9 nM 8.31 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 20876370
Plasmodium falciparum IC50 = 4.9 nM 8.31 Antimalarial activity against Plasmodium falciparum at the ring stage infected i... 20876370
Plasmodium falciparum IC50 = 4.85 nM 8.31 Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum by [3... 18260613
Plasmodium falciparum EC50 = 4.9 nM 8.31 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 23517371
Plasmodium falciparum IC50 = 4.89 nM 8.31 Antimalarial activity against Plasmodium falciparum W2 18330976
Plasmodium falciparum IC50 = 5.02 nM 8.3 In vitro inhibitory activity against chloroquine-resistant Plasmodium falciparum... 12139444

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 59
20421397 10.1128/aac.01421-09 Plasmodium falciparum 50
19995933 10.1128/aac.00354-09 Homo sapiens 25
8450319 10.1021/np50091a005 Unchecked 22
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
21854078 10.1021/jm200647u Plasmodium berghei 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
20813948 10.1126/science.1193225 Plasmodium berghei 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20813948 10.1126/science.1193225 Plasmodium falciparum 12
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 12
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21854078 10.1021/jm200647u Plasmodium falciparum 10
18550377 10.1016/j.bmc.2008.05.017 Plasmodium falciparum 10
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 10
23586757 10.1021/jm400282d Unchecked 10
17371812 10.1128/aac.01607-06 Plasmodium falciparum 10
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 9

Data from ChEMBL 36 via Core Engine