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

CHEMBL506

PRIMAQUINE
💊 Approved Drug
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
💊 Approved Drug
COc1cc(NC(C)CCCN)c2ncccc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL506
Name PRIMAQUINE
Phase Approved
Structure Type MOL
InChI Key INDBQLZJXZLFIT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Kanaprim Maliride Neo-quipenyl NSC-27296 Primachin Primaquina Primaquine SN-13272 WR-2975
27
Targets
133
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names
7
Indications

Molecular Properties

259.4
MW (Da)
2.78
ALogP
4
HBA
2
HBD
60.2
PSA (Ų)
0.84
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1952
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C15H21N3O
MW 259.35
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.43

Indications

Malaria Malaria, Falciparum Malaria, Vivax Pneumonia, Pneumocystis Severe Acute Respiratory Syndrome Glucosephosphate Dehydrogenase Deficiency Obesity

ATC Classification

P01BA03
primaquine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 129 meas. best 8.21
EC50 3 meas. best 5.14
Ki 1 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.21 5.8079 6.2 48
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.07 8.07 8.4 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.8 7.8 16.0 1
Plasmodium yoelii yoelii
CHEMBL612328
 IC50 7.12 6.81 75.7 3
Plasmodium yoelii
CHEMBL612889
 IC50 7.12 6.2433 75.0 3
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.74 6.74 182.4 1
Serine hydroxymethyltransferase, mitochondrial
CHEMBL4295747
 IC50 6.36 6.36 436.5 1
Plasmodium berghei
CHEMBL612653
 IC50 5.96 5.1653 1100.0 30
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.85 5.85 1400.0 1
Unchecked
CHEMBL612545
 IC50 5.72 5.22 1881.7 2
Huh-7
CHEMBL614039
 IC50 5.62 5.62 2400.0 1
Pneumocystis carinii
CHEMBL613064
 IC50 5.6 5.2175 2500.0 4
Thiosulfate sulfurtransferase
CHEMBL4295835
 IC50 5.54 5.54 2900.0 1
GroEL/GroES
CHEMBL4106139
 IC50 5.21 4.665 6200.0 2
MCF7
CHEMBL387
 IC50 5.16 4.7633 6900.0 3
Plasmodium berghei
CHEMBL612653
 EC50 5.14 5.14 7260.0 1
Ribosyldihydronicotinamide dehydrogenase [quinone]
CHEMBL3959
 IC50 5.12 5.12 7500.0 1
SW-620
CHEMBL612262
 IC50 5.04 5.04 9200.0 1
HCT-116
CHEMBL394
 IC50 4.7 4.69 20000.0 2
Leishmania major
CHEMBL612879
 EC50 4.56 4.42 27730.0 2
NCI-H460
CHEMBL396
 IC50 4.52 4.52 30000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.49 4.42 32700.0 3
HEK-293T
CHEMBL3706568
 IC50 4.42 4.42 37640.0 1
Caco-2
CHEMBL614058
 IC50 4.32 4.32 48000.0 1
Leishmania infantum
CHEMBL612848
 IC50 4.26 4.26 54900.0 1
Chloroquine resistance transporter
CHEMBL1795182
 IC50 4.17 4.17 68000.0 1
HT-29
CHEMBL384
 IC50 4.16 4.16 69700.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.12 4.12 75700.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 4.03 4.03 94500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 442.97 ng.hr.mL-1 Homo sapiens
AUC 1256.0 ng.hr.mL-1 Mus musculus
AUC 1314.0 ng.hr.mL-1 Mus musculus
AUC 27450.0 ng.hr.mL-1 Mus musculus
AUC 27665.0 ng.hr.mL-1 Mus musculus
AUC 1256.0 ng.hr.mL-1 Mus musculus
AUC 1314.0 ng.hr.mL-1 Mus musculus
AUC 27450.0 ng.hr.mL-1 Mus musculus
AUC 27665.0 ng.hr.mL-1 Mus musculus
CL 5.8 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 273.58 mL.min-1.kg-1 Mus musculus
CL 12.07 mL.min-1.kg-1 Mus musculus
Cmax 2047.43 nM Mus musculus
Cmax 31417.0 nM Mus musculus
Cmax 2047.43 nM Mus musculus
Cmax 31417.0 nM Mus musculus
F 79.0 % Homo sapiens
Ka 4.2 10^5/M Homo sapiens
Ka 7.0 10^3/M Homo sapiens
MRT 11.0 hr Homo sapiens
MRT 2.3 hr Mus musculus
MRT 4.5 hr Mus musculus
MRT 2.3 hr Mus musculus
MRT 4.5 hr Mus musculus
T1/2 336.0 hr Homo sapiens
T1/2 336.0 hr Homo sapiens
t1/2 - - -
T1/2 7.1 hr Homo sapiens
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 6.17 nM 8.21 Antiplasmodial activity against Plasmodium falciparum F32 assessed as suppressio... 19667291
Plasmodium falciparum IC50 = 7.14 nM 8.15 Antiplasmodial activity against Plasmodium falciparum W2 assessed as suppression... 19667291
Sodium-dependent serotonin transporter Ki = 8.405 nM 8.07 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Plasmodium falciparum IC50 = 8.9 nM 8.05 Antiplasmodial activity against Plasmodium falciparum W2 gametocytes assessed as... 19667291
Plasmodium falciparum IC50 = 8.9 nM 8.05 Antiplasmodial activity against Plasmodium falciparum FcB1/Columbia assessed as ... 19667291
Sodium-dependent serotonin transporter IC50 = 16.0 nM 7.8 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Plasmodium yoelii yoelii IC50 = 75.7 nM 7.12 Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian... 18212104
Plasmodium yoelii IC50 = 75.0 nM 7.12 Antimalarial activity against liver stages of Plasmodium yoelii 265 BY infected ... 22122518
Plasmodium yoelii yoelii IC50 = 75.7 nM 7.12 Antimalarial activity against liver stages of Plasmodium yoelii yoelii 22122518
Cytochrome P450 1A2 IC50 = 182.4 nM 6.74 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Plasmodium falciparum IC50 = 326.0 nM 6.49 Antiplasmodial activity against multidrug-resistant Plasmodium falciparum VS/1 b... 19364853
Plasmodium falciparum IC50 = 326.0 nM 6.49 Antiplasmodial activity against Plasmodium falciparum 3D7 by [3H]hypoxanthine in... 19364853
Plasmodium falciparum IC50 = 400.0 nM 6.4 Antiplasmodial activity against Plasmodium falciparum FCR-3 sporozoites infected... 29754074
Plasmodium falciparum IC50 = 400.0 nM 6.4 Antiplasmodial activity against GFP-harboring Plasmodium falciparum sporozoites ... 30199706
Serine hydroxymethyltransferase, mitochondrial IC50 = 436.52 nM 6.36 Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli B... -
Plasmodium falciparum IC50 = 460.0 nM 6.34 Antimicrobial activity against chloroquine-resistant Plasmodium falciparum K1 25461328
Plasmodium falciparum IC50 = 460.0 nM 6.34 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum 3D7 25461328
Plasmodium falciparum IC50 = 460.0 nM 6.34 Antimicrobial activity against Plasmodium falciparum Dd2 25461328
Plasmodium yoelii yoelii IC50 = 640.0 nM 6.19 Antimalarial activity against Plasmodium yoelii 265 sporozoites in primary mice ... 18456502
Plasmodium falciparum IC50 = 643.0 nM 6.19 Antimalarial activity against Plasmodium falciparum K1 assessed as inhibition of... 24900574

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 227
- 10.5281/zenodo.13943903 ADMET 85
31158845 10.1038/s41586-019-1291-3 ADMET 47
32390431 10.1021/acs.jmedchem.0c00539 ADMET 16
30852885 10.1021/acs.jmedchem.8b01961 ADMET 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
3528491 10.1021/jm00159a034 Mus musculus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
7131489 10.1021/jm00351a018 Mus musculus 6
15689174 10.1021/jm0494624 Unchecked 6
33166927 10.1016/j.bmc.2020.115832 Plasmodium gallinaceum 6
6770089 10.1021/jm00179a023 Mus musculus 6
7131488 10.1021/jm00351a017 Mus musculus 6
19799426 10.1021/jm900738c Pneumocystis carinii 5
27614409 10.1016/j.ejmech.2016.08.021 Staphylococcus aureus 5
18653332 10.1016/j.bmcl.2008.07.013 Plasmodium falciparum 5
2666665 10.1021/jm00128a010 Mus musculus 5
6750123 10.1021/jm00350a016 Mus musculus 5
4068013 10.1021/jm00150a035 Mus musculus 4

Data from ChEMBL 36 via Core Engine