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Compound Detail

CHEMBL43128

PRIMAQUINE PHOSPHATE
💊 Approved Drug
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💊 Approved Drug
COc1cc(NC(C)CCCN)c2ncccc2c1.O=P(O)(O)O.O=P(O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL43128
Name PRIMAQUINE PHOSPHATE
Phase Approved
Structure Type MOL
InChI Key GJOHLWZHWQUKAU-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL506
Active Moiety CHEMBL506

Known Names

Camden Malquine NSC-149765 Primaquine diphosphate Primaquine phosphate Primaquini diphosphas WR 2975
13
Targets
21
Activities
1
Assay Types
2
PK Parameters
20
Publications
7
Known Names
2
Indications
1
Mechanisms

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

Extended Properties

Molecular Formula C15H27N3O9P2
MW 455.34
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Malaria, Falciparum Malaria

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 21 meas. best 6.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 6.38 6.04 415.0 6
MCF7
CHEMBL387
 IC50 5.3 5.18 5000.0 2
A2780
CHEMBL614004
 IC50 5.3 5.3 5000.0 1
Plasmodium berghei
CHEMBL612653
 IC50 5.13 5.13 7400.0 1
NCI-H460
CHEMBL396
 IC50 5.0 4.85 10000.0 2
HEK293
CHEMBL614818
 IC50 4.96 4.96 10960.0 1
HL-60
CHEMBL383
 IC50 4.95 4.95 11360.0 1
K562
CHEMBL385
 IC50 4.92 4.92 12040.0 1
HCT-116
CHEMBL394
 IC50 4.85 4.6 13990.0 2
SW-620
CHEMBL612262
 IC50 4.85 4.85 14000.0 1
CAPAN-1
CHEMBL614536
 IC50 4.85 4.85 14240.0 1
L6
CHEMBL614793
 IC50 4.22 4.22 59500.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 4.1 10^5/M Homo sapiens
Ka 8.0 10^5/M Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 415.0 nM 6.38 Antimalarial activity against blood stage chloroquine-sensitive Plasmodium falci... 39149112
Plasmodium falciparum IC50 = 464.0 nM 6.33 Antimalarial activity against blood stage chloroquine-resistant Plasmodium falci... 39149112
Plasmodium falciparum IC50 = 794.0 nM 6.1 HARVARD: Inhibition of blood stage Plasmodium falciparum Dd2 infection 22586124
Plasmodium falciparum IC50 = 1300.0 nM 5.89 Antiplasmodial activity against asexual chloroquine sensitive blood stage Plasmo... 31431364
Plasmodium falciparum IC50 = 1500.0 nM 5.82 Antiplasmodial activity against erythrocytic stage of Plasmodium falciparum NF54... 29407988
Plasmodium falciparum IC50 = 1900.0 nM 5.72 Antiplasmodial activity against asexual chloroquine resistant blood stage Plasmo... 31431364
MCF7 IC50 = 5000.0 nM 5.3 Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs... 29407988
A2780 IC50 = 5000.0 nM 5.3 Cytotoxicity against human A2780 cells assessed as growth inhibition after 72 hr... 29407988
Plasmodium berghei IC50 = 7400.0 nM 5.13 HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells 22586124
MCF7 IC50 = 8730.0 nM 5.06 Antiproliferative activity against human MCF7 cells measured after 72 hrs by MTT... 31431364
NCI-H460 IC50 = 10000.0 nM 5.0 Cytotoxicity against human NCI-H460 cells assessed as growth inhibition after 72... 29407988
HEK293 IC50 = 10960.0 nM 4.96 Antiproliferative activity against human HEK293 cells measured after 72 hrs by M... 31431364
HL-60 IC50 = 11360.0 nM 4.95 Cytotoxicity against human HL60 cells assessed as growth inhibition after 72 hrs... 29407988
K562 IC50 = 12040.0 nM 4.92 Cytotoxicity against human K562 cells assessed as growth inhibition after 72 hrs... 29407988
SW-620 IC50 = 14000.0 nM 4.85 Cytotoxicity against human SW620 cells assessed as growth inhibition after 72 hr... 29407988
CAPAN-1 IC50 = 14240.0 nM 4.85 Cytotoxicity against human Capan1 cells assessed as growth inhibition after 72 h... 29407988
HCT-116 IC50 = 13990.0 nM 4.85 Antiproliferative activity against human HCT116 cells measured after 72 hrs by M... 31431364
NCI-H460 IC50 = 19840.0 nM 4.7 Antiproliferative activity against human H460 cells measured after 72 hrs by MTT... 31431364
HCT-116 IC50 = 44220.0 nM 4.35 Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 h... 29407988
L6 IC50 = 59500.0 nM 4.22 Cytotoxicity against rat L6 cells assessed as reduction in cell viability after ... 29407988

Literature References

PubMed DOI Target Context # Activities
7205891 10.1021/jm00134a019 Mus musculus 12
7131488 10.1021/jm00351a017 Mus musculus 7
4067985 10.1021/jm00149a004 Mus musculus 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
409843 10.1021/jm00220a025 Plasmodium cynomolgi 4
39149112 10.1039/d4md00007b Plasmodium falciparum 4
7131488 10.1021/jm00351a017 Plasmodium cynomolgi 3
29407988 10.1016/j.ejmech.2018.01.062 MCF7 3
31431364 10.1016/j.bmcl.2019.08.018 Plasmodium falciparum 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
22586124 10.1073/pnas.1118370109 Plasmodium berghei 1
22586124 10.1073/pnas.1118370109 Plasmodium falciparum 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
29407988 10.1016/j.ejmech.2018.01.062 Unchecked 1
29407988 10.1016/j.ejmech.2018.01.062 L6 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
29407988 10.1016/j.ejmech.2018.01.062 NCI-H460 1
39149112 10.1039/d4md00007b Erythrocyte 1
29407988 10.1016/j.ejmech.2018.01.062 SW-620 1
18289858 10.1016/j.bmc.2008.01.053 Unchecked 1

Data from ChEMBL 36 via Core Engine