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Compound Detail

CHEMBL535650

MEFLOQUINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.OC(c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)C1CCCCN1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL535650
Name MEFLOQUINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key WESWYMRNZNDGBX-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL416956
Active Moiety CHEMBL416956

Known Names

Fansimef Lariam Loriam Mefloquine hcl Mefloquine hydrochloride Mefloquini hydrochloridum NSC-157387 RO 21-5998/001 RO-21-5998 RO-21-5998/001 RO-215998001 WR-142490
4
Targets
18
Activities
2
Assay Types
0
PK Parameters
18
Publications
12
Known Names
3
Indications
1
Mechanisms

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 1984

Extended Properties

Molecular Formula C17H17ClF6N2O
MW 414.78
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.03

Mechanism of Action

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

Indications

Malaria Malaria, Falciparum Malaria, Vivax

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 17 meas. best 8.72
EC50 1 meas. best 5.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.72 8.208 1.9 10
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.25 5.25 5623.4 1
SARS-CoV-2
CHEMBL4303835
 IC50 5.15 5.03 7110.0 3
Unchecked
CHEMBL612545
 EC50 5.12 5.12 7610.0 1
Unchecked
CHEMBL612545
 IC50 4.72 4.61 19150.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 1.9 nM 8.72 Growth inhibition after 72 hrs of Plasmodium falciparum W2 by HRPII ELISA 17220424
Plasmodium falciparum IC50 = 3.1 nM 8.51 Growth inhibition after 72 hrs of Plasmodium falciparum W2 by SYBR green I assay 17220424
Plasmodium falciparum IC50 = 4.7 nM 8.33 Growth inhibition after 72 hrs of Plasmodium falciparum D6 by HRPII ELISA 17220424
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against multidrug-resistant Plasmodium falciparum thailand... 25801154
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against chloroquine-resistant Plasmodium falciparum indoch... 25801154
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antimalarial activity against chloroquine-susceptible Plasmodium falciparum afri... 25801154
Plasmodium falciparum IC50 = 6.4 nM 8.19 Growth inhibition after 72 hrs of Plasmodium falciparum D6 by SYBR green I assay 17220424
Plasmodium falciparum IC50 = 8.4 nM 8.08 Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by HRPII ELISA 17220424
Plasmodium falciparum IC50 = 9.4 nM 8.03 Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by SYBR green assay 17220424
Plasmodium falciparum IC50 = 40.0 nM 7.4 Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by mi... 21995505
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 5623.41 nM 5.25 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
SARS-CoV-2 IC50 = 7110.0 nM 5.15 IC50 determination at MOI 0.004 using CellTiter- Glo (CTG) assay, performed 3 da... -
Unchecked EC50 = 7610.0 nM 5.12 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
SARS-CoV-2 IC50 = 8060.0 nM 5.09 IC50 determination at MOI 0.01 using CellTiter- Glo (CTG) assay, performed 3 day... -
SARS-CoV-2 IC50 = 14150.0 nM 4.85 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
Unchecked IC50 = 19150.0 nM 4.72 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked IC50 = 20270.0 nM 4.69 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 37565.0 nM 4.42 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -

Literature References

PubMed DOI Target Context # Activities
17220424 10.1128/aac.01313-06 Plasmodium falciparum 12
19164150 10.1128/aac.00241-08 Plasmodium falciparum 3
25801154 10.1016/j.bmc.2015.02.061 Plasmodium falciparum 3
- 10.1101/2020.03.25.008482 SARS-CoV-2 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
- 10.1101/2020.03.25.008482 ADMET 2
- 10.1101/2020.03.25.008482 Vero C1008 2
26453006 10.1016/j.bmcl.2015.09.034 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 1
26453006 10.1016/j.bmcl.2015.09.034 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 1
21995505 10.1021/np200429b Plasmodium falciparum 1
19186946 10.1021/jm801484v Plasmodium berghei 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
12873512 10.1016/s0960-894x(03)00492-x Voltage-gated inwardly rectifying potassium channel KCNH2 1
- 10.21203/rs.3.rs-23951/v1 Caco-2 1
- 10.21203/rs.3.rs-23951/v1 ADMET 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1016/S0960-894X(00)80654-X Mus musculus 1

Data from ChEMBL 36 via Core Engine