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Compound Detail

CHEMBL38827

LUMEFANTRINE
💊 Approved Drug
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💊 Approved Drug
CCCCN(CCCC)CC(O)c1cc(Cl)cc2c1-c1ccc(Cl)cc1/C2=C/c1ccc(Cl)cc1

Basic Information

ChEMBL ID CHEMBL38827
Name LUMEFANTRINE
Phase Approved
Structure Type MOL
InChI Key DYLGFOYVTXJFJP-MYYYXRDXSA-N
Therapeutic ✓ Yes

Known Names

Benflumelol Benflumetol CPG-56695 Dl-benflumelol GNF-PF-1971 Lumefantrina Lumefantrine Lumefantrine component of coartem Lumefantrinum
3
Targets
75
Activities
2
Assay Types
19
PK Parameters
20
Publications
9
Known Names
6
Indications
1
Mechanisms

Molecular Properties

529.0
MW (Da)
9.15
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.22
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Year 2008

Extended Properties

Molecular Formula C30H32Cl3NO
MW 528.95
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.60

Mechanism of Action

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

Indications

Malaria Fever Malaria, Falciparum Malaria, Vivax Schistosomiasis haematobia HIV Infections

Activity Summary

IC50 72 meas. best 9.72
EC50 3 meas. best 9.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.72 7.95 0.2 63
Plasmodium falciparum
CHEMBL364
EC50 9.35 7.25 0.5 3
Plasmodium vivax
CHEMBL613013
IC50 7.84 7.63 14.6 5
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.42 5.755 377.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 210040.0 ng.hr.mL-1 Homo sapiens
AUC 194740.0 ng.hr.mL-1 Homo sapiens
AUC 472000.0 ng.hr.mL-1 Homo sapiens
CL 6.11 L/hr Homo sapiens
CL 1.82 L/hr Homo sapiens
Cmax 12774.36 nM Homo sapiens
Cmax 3922.87 nM Homo sapiens
Cmax 4692.31 nM Homo sapiens
Cmax 4588.34 nM Homo sapiens
Cmax 593.63 nM Homo sapiens
Cmax 941.49 nM Homo sapiens
Cmax 818.6 nM Homo sapiens
Cmax 92.64 nM Homo sapiens
Ka 0.0588 /hr Homo sapiens
T1/2 32.7 hr Homo sapiens
T1/2 79.2 hr Homo sapiens
T1/2 72.0 hr Homo sapiens
Vz 20.2 l Homo sapiens
Vz 181.0 l Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.19 nM 9.72 Antimicrobial activity against Plasmodium falciparum harboring mdr1 N86Y/D1246Y/... 20065051
Plasmodium falciparum IC50 = 0.31 nM 9.51 Antimicrobial activity against chloroquine-resistant Plasmodium falciparum K1 by... 20065051
Plasmodium falciparum EC50 = 0.45 nM 9.35 Antiplasmodial activity against multidrug-resistant Plasmodium falciparum W2 inf... 23587422
Plasmodium falciparum IC50 = 0.45 nM 9.35 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum W2 by... 20065051
Plasmodium falciparum IC50 = 0.51 nM 9.29 Antimicrobial activity against Plasmodium falciparum by ELISA 20065051
Plasmodium falciparum IC50 = 1.41 nM 8.85 Antimicrobial activity against chloroquine-resistant Plasmodium falciparum HB3 b... 20065051
Plasmodium falciparum IC50 = 1.82 nM 8.74 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum D6 by... 20065051
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antiplasmodial activity against multidrug resistant asexual blood stage Plasmodi... 33666415
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 30852885
Plasmodium falciparum IC50 = 3.2 nM 8.49 Antimalarial activity against Plasmodium falciparum 3D7A asexual forms assessed ... 31911292
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 4.2 nM 8.38 Antimalarial activity against Plasmodium falciparum clinical isolates measured a... 32390431
Plasmodium falciparum IC50 = 4.5 nM 8.35 Antimalarial activity against drug-resistant Plasmodium falciparum 3D7 harboring... 30852885
Plasmodium falciparum IC50 = 5.7 nM 8.24 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antiplasmodial activity against chloroquine-sensitive asexual blood stage Plasmo... 33666415
Plasmodium falciparum IC50 = 6.5 nM 8.19 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 8.0 nM 8.1 Antimalarial activity against Plasmodium falciparum IMT 9881 assessed as incorpo... 19307369
Plasmodium falciparum IC50 = 8.0 nM 8.1 Antimalarial activity against Plasmodium falciparum IMT 10336 assessed as incorp... 19307369
Plasmodium falciparum IC50 = 8.0 nM 8.1 Antimalarial activity against Plasmodium falciparum IMT K2 assessed as incorpora... 19307369

Literature References

PubMed DOI Target Context # Activities
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
19564366 10.1128/aac.00195-09 Homo sapiens 20
19770282 10.1128/aac.00638-09 Plasmodium falciparum 12
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 6
20065051 10.1128/aac.01412-09 Plasmodium falciparum 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19841149 10.1128/aac.00679-09 Homo sapiens 4
18180357 10.1128/aac.01334-07 Plasmodium vivax 4
25311562 10.1016/j.bmc.2014.09.040 Plasmodium falciparum 3
19364853 10.1128/aac.01689-08 Plasmodium falciparum 3
22128829 10.1021/jm201214d Plasmodium berghei 2
11844668 10.1016/s0960-894x(01)00798-3 Plasmodium falciparum 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
33666415 10.1021/acs.jmedchem.0c01744 Plasmodium berghei 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
33666415 10.1021/acs.jmedchem.0c01744 Plasmodium falciparum 2
18411319 10.1128/aac.00282-08 Plasmodium falciparum 1
36940609 10.1016/j.bmc.2023.117239 Chikungunya virus 1
15324906 10.1016/j.bmcl.2004.06.070 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine