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Compound Detail

CHEMBL7568

QUINACRINE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)cc12

Basic Information

ChEMBL ID CHEMBL7568
Name QUINACRINE
Phase Approved
Structure Type MOL
InChI Key GPKJTRJOBQGKQK-UHFFFAOYSA-N

Known Names

Atabrine GNF-Pf-5448 Mepacrina Mepacrine Quinacrine
58
Targets
145
Activities
4
Assay Types
8
PK Parameters
20
Publications
5
Known Names
6
Indications

Molecular Properties

400.0
MW (Da)
5.97
ALogP
4
HBA
1
HBD
37.4
PSA (Ų)
0.45
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product
USAN Stem -crine

Extended Properties

Molecular Formula C23H30ClN3O
MW 399.97
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.99

Indications

Amebiasis Carcinoma, Renal Cell Creutzfeldt-Jakob Syndrome Prostatic Neoplasms, Castration-Resistant Carcinoma, Non-Small-Cell Lung Colorectal Neoplasms

ATC Classification

P01AX05
mepacrine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Drug Warnings

Withdrawn
General Warning
questions about the safety of the drug
Country: India   Year: 1998

Activity Summary

IC50 83 meas. best 7.89
EC50 38 meas. best 8.3
Ki 22 meas. best 6.58
Kd 2 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
EC50 8.3 7.8733 5.0 9
Plasmodium falciparum
CHEMBL364
IC50 7.89 7.1863 13.0 8
Major prion protein
CHEMBL3698
IC50 7.02 7.02 95.1 1
UV4
CHEMBL612800
IC50 6.85 6.85 140.0 1
Plasmodium yoelii
CHEMBL612889
IC50 6.78 6.78 165.7 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.64 6.1123 230.0 13
U2OS
CHEMBL615023
EC50 6.6 6.6 250.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.58 6.58 266.0 1
Riboflavin-binding protein
CHEMBL1944489
Kd 6.58 6.58 264.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.56 6.56 277.0 1
ScN2a
CHEMBL613872
EC50 6.52 6.3067 300.0 3
Major prion protein
CHEMBL4869
EC50 6.52 6.52 300.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.46 6.46 343.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.45 6.45 359.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.35 6.35 448.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.25 6.25 560.0 1
Unchecked
CHEMBL612545
Ki 6.14 6.02 719.0 4
Unchecked
CHEMBL612545
IC50 6.13 5.3486 739.0 7
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.12 6.12 761.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.08 6.08 833.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.07 6.07 855.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 6.02 6.02 964.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.99 5.99 1015.0 1
Ebolavirus
CHEMBL4434621
IC50 5.98 5.98 1050.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.96 5.96 1100.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 5.9 5.9 1255.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.88 5.88 1318.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.83 5.83 1489.0 1
CHO-AA8
CHEMBL614555
IC50 5.77 5.77 1700.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.74 5.74 1825.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 5.72 5.72 1890.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.7 5.7 1983.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.68 5.68 2065.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.64 5.64 2280.0 1
Zika virus
CHEMBL4296612
EC50 5.64 5.64 2270.0 1
U2OS
CHEMBL615023
IC50 5.6 5.6 2500.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.58 5.58 2663.0 1
Acetylcholinesterase
CHEMBL220
IC50 5.57 5.57 2667.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 5.57 5.57 2684.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.54 5.54 2872.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.54 5.54 2896.0 1
MDA-MB-231
CHEMBL400
IC50 5.49 5.49 3250.0 2
Aldehyde oxidase
CHEMBL3257
IC50 5.48 5.48 3300.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 5.48 5.48 3300.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 5.47 5.47 3414.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.46 5.46 3476.0 1
Histamine H2 receptor
CHEMBL1941
IC50 5.45 5.45 3535.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 5.43 5.43 3736.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.41 5.41 3857.0 1
MDA-MB-468
CHEMBL614335
IC50 5.4 5.4 3960.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 5.1 mL.min-1.kg-1 Homo sapiens
Fu 0.103 - -
Fu 0.0002 - -
Fu 0.103 - Homo sapiens
Fu 0.13 - Homo sapiens
Ka 7.0 10^3/M Homo sapiens
MRT 150.0 hr Homo sapiens
T1/2 120.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 5.0 nM 8.3 Effective concentration for Plasmodium falciparum 3D7 15686903
Plasmodium falciparum EC50 = 8.0 nM 8.1 Effective concentration against Plasmodium falciparum W2 15686903
Plasmodium falciparum EC50 = 8.0 nM 8.1 Effective concentration for Plasmodium falciparum 3D7 15686903
Plasmodium falciparum EC50 = 8.13 nM 8.09 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 11.0 nM 7.96 Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum 3D7 a... 17371810
Plasmodium falciparum IC50 = 13.0 nM 7.89 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... -
Plasmodium falciparum EC50 = 14.22 nM 7.85 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum IC50 = 18.0 nM 7.75 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 29.0 nM 7.54 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum IC50 = 29.0 nM 7.54 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum EC50 = 32.0 nM 7.5 Effective concentration against Plasmodium falciparum W2 15686903
Plasmodium falciparum EC50 = 33.0 nM 7.48 Antimalarial activity against blood stage Plasmodium falciparum 3D7 assessed as ... 36736152
Plasmodium falciparum EC50 = 33.0 nM 7.48 Antimicrobial activity against chloroquine-resistant Plasmodium falciparum W2 af... 17371810
Plasmodium falciparum IC50 = 43.0 nM 7.37 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 aft... 18395298
Plasmodium falciparum IC50 = 43.0 nM 7.37 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 ass... -
Major prion protein IC50 = 95.1 nM 7.02 Synergistic anti-prion activity of mouse ScN2a cells infected with RML prion ass... 35771181
UV4 IC50 = 140.0 nM 6.85 In vitro cytotoxicity against transformed chinese hamster fibroblast line UV4. 2319563
Plasmodium yoelii IC50 = 165.7 nM 6.78 NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ... 22096101
NON-PROTEIN TARGET EC50 = 230.0 nM 6.64 Antiprion activity against scrapie prion protein RML infected mouse ScN2a cells ... 18556207

Literature References

Data from ChEMBL 36 via Core Engine