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Compound Detail

CHEMBL170

QUININE
💊 Approved Drug
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💊 Approved Drug
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12

Basic Information

ChEMBL ID CHEMBL170
Name QUININE
Phase Approved
Structure Type MOL
InChI Key LOUPRKONTZGTKE-WZBLMQSHSA-N
Therapeutic ✓ Yes

Known Names

(8s,9r)-6'-methoxycinchonan-9-ol Chininum purum NSC-192949 Quinine Rezquin WR297608
26
Targets
405
Activities
4
Assay Types
13
PK Parameters
20
Publications
6
Known Names
5
Indications

Molecular Properties

324.4
MW (Da)
3.17
ALogP
4
HBA
1
HBD
45.6
PSA (Ų)
0.88
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem sal-
USAN Year 1980

Extended Properties

Molecular Formula C20H24N2O2
MW 324.42
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.83

Indications

Malaria Malaria, Falciparum Chronic Pain Immunologic Deficiency Syndromes Severe Acute Respiratory Syndrome

ATC Classification

M09AA72
quinine, combinations with psycholeptics
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: OTHER DRUGS FOR DISORDERS OF THE MUSCULO-SKELETAL SYSTEM
P01BC01
quinine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 378 meas. best 9.15
Ki 13 meas. best 6.03
EC50 12 meas. best 6.96
Kd 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.15 6.7115 0.7 314
Cytochrome P450 2D6
CHEMBL289
IC50 8.0 6.6533 10.0 3
Cytochrome P450 2D26
CHEMBL2483
IC50 7.03 7.03 94.0 1
Plasmodium falciparum
CHEMBL364
EC50 6.96 6.62 110.0 6
Solute carrier family 22 member 1
CHEMBL2073664
IC50 6.55 6.55 280.0 1
Solute carrier family 22 member 1
CHEMBL2073670
IC50 6.05 5.8 900.0 3
Solute carrier family 22 member 1
CHEMBL2073670
Ki 6.03 5.7 930.0 2
Cytochrome P450 2D4
CHEMBL4982
IC50 5.77 5.77 1700.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 5.77 4.6525 1700.0 4
Solute carrier family 22 member 2
CHEMBL2073662
IC50 5.55 5.55 2800.0 1
Solute carrier family 22 member 2
CHEMBL1743122
Ki 5.47 5.47 3400.0 1
Unchecked
CHEMBL612545
IC50 5.46 4.5233 3500.0 9
Solute carrier organic anion transporter family member 1A4
CHEMBL1781860
Ki 5.42 5.42 3810.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 5.36 5.36 4400.0 1
Cytochrome P450 2D6
CHEMBL289
Ki 5.34 4.984 4600.0 5
Leishmania major
CHEMBL612879
EC50 5.03 5.025 9410.0 2
ScN2a
CHEMBL613872
IC50 5.0 5.0 10000.0 1
Cytochrome P450 2D3
CHEMBL3057
IC50 4.92 4.92 12000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
Ki 4.92 4.92 12000.0 1
Solute carrier family 22 member 2
CHEMBL1770032
IC50 4.89 4.655 13000.0 2
ADMET
CHEMBL612558
IC50 4.69 4.69 20250.0 1
Trypanosoma brucei brucei
CHEMBL612851
IC50 4.67 4.67 21200.0 1
Solute carrier family 22 member 1
CHEMBL5685
Ki 4.64 4.64 22900.0 1
MES-SA/Dx5
CHEMBL613827
IC50 4.37 4.27 43000.0 2
Cytochrome P450 2D1
CHEMBL2475
IC50 4.33 4.33 46500.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.29 4.29 51600.0 1
Solute carrier family 22 member 2
CHEMBL1770032
Ki 4.26 4.26 55000.0 1
Heme
CHEMBL4651321
IC50 4.19 4.19 65000.0 1
Solute carrier organic anion transporter family member 1A1
CHEMBL1781859
Ki 4.12 4.12 76700.0 1
MES-SA
CHEMBL614343
IC50 4.04 4.035 91000.0 2
Bile salt export pump
CHEMBL6020
IC50 4.0 4.0 98830.0 1
FM3A
CHEMBL614297
EC50 4.0 4.0 100000.0 4

Pharmacokinetic Data

Parameter Value Units Species
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 80.0 % Homo sapiens
Fu 0.3 - Homo sapiens
Fu 0.3 - Homo sapiens
Fu 0.082 - Rattus norvegicus
Ka 0.2 10^5/M -
MRT 16.0 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
Vd 43.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.7 nM 9.15 Antiplasmodial against chloroquine-sensitive Plasmodium falciparum 3D7 assessed ... 23064162
Plasmodium falciparum IC50 = 5.8 nM 8.24 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCM29 ... 19908867
Plasmodium falciparum IC50 = 6.7 nM 8.17 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum IMT K2... 19908867
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of human CYP2D6 preincubated for 5 mins followed by NADPH addition an... 31734022
Plasmodium falciparum IC50 = 11.0 nM 7.96 Antimalarial activity against Plasmodium falciparum D6 in MSF assay 18023189
Plasmodium falciparum IC50 = 12.0 nM 7.92 Antimalarial activity against Plasmodium falciparum K1 19084293
Plasmodium falciparum IC50 = 15.4 nM 7.81 Antimicrobial activity against Plasmodium falciparum harboring mdr1 N86Y/D1246Y/... 20065051
Plasmodium falciparum IC50 = 18.0 nM 7.75 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 28800458
Plasmodium falciparum IC50 = 18.0 nM 7.75 Antiplasmodial activity against CQ-sensitive Plasmodium falciparum 3D7 25593097
Plasmodium falciparum IC50 = 18.0 nM 7.75 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 28800458
Plasmodium falciparum IC50 = 18.0 nM 7.75 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 29360043
Plasmodium falciparum IC50 = 18.7 nM 7.73 Antiplasmodial against chloroquine-rsistant Plasmodium falciparum W2 after 2 day... 23064162
Plasmodium falciparum IC50 = 18.67 nM 7.73 Antiplasmodial activity against chloroquine-resistant ring stage Plasmodium falc... 24287561
Plasmodium falciparum IC50 = 20.0 nM 7.7 Antimalarial activity against Plasmodium falciparum isolate 8973 20516285
Plasmodium falciparum IC50 = 20.4 nM 7.69 Antiplasmodial against chloroquine-rsistant Plasmodium falciparum K1 assessed as... 23064162
Plasmodium falciparum IC50 = 22.0 nM 7.66 Antimalarial activity against Plasmodium falciparum isolate AK022 D-28 20516285
Plasmodium falciparum IC50 = 22.0 nM 7.66 Antimalarial activity against CQ-sensitive Plasmodium falciparum NF54 34655985
Plasmodium falciparum IC50 = 23.38 nM 7.63 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 i... 9917283
Plasmodium falciparum IC50 = 27.1 nM 7.57 Antimalarial activity against Plasmodium falciparum 3D7 20516285
Plasmodium falciparum IC50 = 27.8 nM 7.56 Antimalarial activity against Plasmodium falciparum isolate 8948 20516285

Literature References

PubMed DOI Target Context # Activities
20643902 10.1128/aac.00321-10 Plasmodium falciparum 76
20516285 10.1128/aac.00325-10 Plasmodium falciparum 45
19273668 10.1128/aac.01243-08 Plasmodium falciparum 27
20329733 10.1021/jm9018383 Plasmodium falciparum 24
20547801 10.1128/aac.00183-10 Plasmodium falciparum 23
8450319 10.1021/np50091a005 Unchecked 22
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
19734910 10.1038/nchembio.215 Plasmodium falciparum 14
19908867 10.1021/jm901357n Plasmodium falciparum 11
18024584 10.1073/pnas.0709695104 H4 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23586757 10.1021/jm400282d Unchecked 11
17371812 10.1128/aac.01607-06 Plasmodium falciparum 10
6195312 10.1021/np50028a027 CHO 8
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20017491 10.1021/jm900672t Plasmodium berghei 7
11716514 10.1006/bbrc.2001.6000 ATP-dependent translocase ABCB1 7
17116669 10.1128/aac.01023-06 Plasmodium falciparum 7
7009867 10.1021/jm00134a002 Plasmodium berghei 7

Data from ChEMBL 36 via Core Engine