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Compound Detail

CHEMBL1294

QUINIDINE
💊 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 CHEMBL1294
Name QUINIDINE
Phase Approved
Structure Type MOL
InChI Key LOUPRKONTZGTKE-LHHVKLHASA-N
Therapeutic ✓ Yes

Known Names

(8r,9s)-quinidine .beta.-quinidine Conquinine Kinidin Pitayine Quinidine
36
Targets
166
Activities
4
Assay Types
30
PK Parameters
20
Publications
6
Known Names
15
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 1950
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

Extended Properties

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

Indications

Arrhythmias, Cardiac Amyotrophic Lateral Sclerosis Atrial Fibrillation Death, Sudden, Cardiac Multiple Sclerosis Myocardial Infarction Ventricular Fibrillation Depressive Disorder Depressive Disorder, Major Migraine Disorders Constipation Hepatitis B, Chronic Non-alcoholic Fatty Liver Disease Respiratory Syncytial Virus Infections Severe Acute Respiratory Syndrome

ATC Classification

C01BA01
quinidine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C01BA51
quinidine, combinations excl. psycholeptics
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C01BA71
quinidine, combinations with psycholeptics
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

IC50 136 meas. best 8.7
Ki 18 meas. best 8.01
EC50 11 meas. best 8.02
Kd 1 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2D6
CHEMBL289
IC50 8.7 7.3052 2.0 69
Plasmodium falciparum
CHEMBL364
IC50 8.4 7.0656 4.0 9
Plasmodium falciparum
CHEMBL364
EC50 8.02 7.735 9.6 2
Cytochrome P450 2D6
CHEMBL289
Ki 8.01 7.4367 9.8 6
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.52 6.2429 300.0 7
ATP-dependent translocase ABCB1
CHEMBL4302
Ki 6.37 5.628 430.0 5
Cavia porcellus
CHEMBL369
Kd 6.0 6.0 1000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 6.0 5.1863 1000.0 8
Cholinesterase
CHEMBL1914
IC50 5.91 5.91 1230.0 1
A-type voltage-gated potassium channel KCND2
CHEMBL1075227
IC50 5.66 5.66 2200.0 1
Cytochrome P450 2D26
CHEMBL2483
IC50 5.55 5.55 2800.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 5.5 5.5 3200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.47 5.3129 3380.0 7
ScN2a
CHEMBL613872
IC50 5.3 5.3 5000.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL3762
IC50 5.25 5.125 5600.0 2
Solute carrier family 22 member 1
CHEMBL2073670
Ki 5.22 5.03 6000.0 2
Voltage-gated L-type calcium channel
CHEMBL2095229
IC50 5.19 5.19 6400.0 1
Sodium channel protein type 5 subunit alpha
CHEMBL1980
IC50 5.16 4.97 6900.0 2
Potassium voltage-gated channel subfamily A member 5
CHEMBL4306
IC50 5.14 5.14 7300.0 1
Cholinesterase
CHEMBL5763
IC50 5.13 5.13 7370.0 1
Solute carrier organic anion transporter family member 1A1
CHEMBL1781859
Ki 5.03 5.03 9270.0 1
ATP-dependent translocase ABCB1
CHEMBL3467
IC50 5.0 5.0 10000.0 2
Unchecked
CHEMBL612545
EC50 4.99 4.99 10260.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 4.95 4.95 11200.0 1
Solute carrier family 22 member 1
CHEMBL2073670
IC50 4.9 4.9 12700.0 1
ATP-dependent translocase ABCB1
CHEMBL2573
IC50 4.89 4.89 13000.0 2
Solute carrier family 22 member 2
CHEMBL1770032
IC50 4.84 4.84 14600.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
IC50 4.81 4.81 15600.0 2
Potassium channel subfamily T member 1
CHEMBL4739688
IC50 4.8 4.45 15800.0 2
Solute carrier family 22 member 1
CHEMBL5685
Ki 4.76 4.76 17500.0 1
Solute carrier family 22 member 2
CHEMBL1770032
Ki 4.72 4.72 19100.0 1
Cytochrome P450 2D1
CHEMBL2475
IC50 4.7 4.7 19900.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 4.7 4.7 19820.0 1
Unchecked
CHEMBL612545
IC50 4.64 4.64 23000.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.63 4.63 23400.0 1
Heme
CHEMBL4651321
IC50 4.62 4.62 24000.0 1
Trypanosoma brucei brucei
CHEMBL612851
IC50 4.58 4.58 25990.0 1
Cytochrome P450 2D3
CHEMBL3057
IC50 4.57 4.57 26900.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.55 4.55 28000.0 1
Cytochrome P450 2C9
CHEMBL3397
Ki 4.5 4.5 32000.0 1
ADMET
CHEMBL612558
IC50 4.46 4.46 34810.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.34 4.34 45800.0 1
Cytochrome P450 2D4
CHEMBL4982
IC50 4.33 4.33 47200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1880.0 ng.hr.mL-1 Rattus norvegicus
AUC 1850.0 ng.hr.mL-1 Rattus norvegicus
AUC 304.0 ng.hr.mL-1 Rattus norvegicus
AUC 302.0 ng.hr.mL-1 Rattus norvegicus
AUC 5310.0 ng.hr.mL-1 Rattus norvegicus
AUC 4920.0 ng.hr.mL-1 Rattus norvegicus
CL 5.33 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 3.4 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.5 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 13.0 mL.min-1.kg-1 Macaca
CL 34.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.17 uL.min-1.(10^6cells)-1 Homo sapiens
CL 72.44 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 33.3 mL.min-1.kg-1 Homo sapiens
CL 13.5 uL.min-1.(10^6cells)-1 Homo sapiens
CL 20.3 uL.min-1.(10^6cells)-1 Homo sapiens
CL 4.02 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
F 75.0 % Homo sapiens
Fu 0.13 - -
Fu 0.019 - -
Fu 0.13 - Homo sapiens
Fu 0.26 - Homo sapiens
Fu 0.26 - Homo sapiens
Fu 0.09 - Rattus norvegicus
Fu 0.251 - Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2D6 IC50 = 2.0 nM 8.7 Inhibition of human recombinant microsomal CYP2D6 using {3-[2-(N,N-diethyl-N-met... 24050112
Cytochrome P450 2D6 IC50 = 3.3 nM 8.48 Inhibition of MAMC O-dealkylation mediated by human Cytochrome P450 2D6 expresse... 12502361
Plasmodium falciparum IC50 = 4.0 nM 8.4 In vitro inhibition of parasite development of Plasmodium falciparum W2 in human... 11992775
Cytochrome P450 2D6 IC50 = 6.9 nM 8.16 Inhibition of human recombinant CYP2D6 using luciferin as substrate preincubated... 28797771
Cytochrome P450 2D6 IC50 = 7.3 nM 8.14 Inhibition of CYP2D6 (unknown origin) expressed in insect cell microsomes using ... 32573250
Cytochrome P450 2D6 IC50 = 8.1 nM 8.09 Inhibition of human recombinant CYP2D6 30721053
Cytochrome P450 2D6 IC50 = 9.0 nM 8.05 Fluorescent High Throughput P450 Assays: The interaction of SC12 with cytochrome... -
Cytochrome P450 2D6 IC50 = 9.0 nM 8.05 Fluorescent High Throughput P450 Assay: The interaction of SC12 with cytochrome ... -
Cytochrome P450 2D6 IC50 = 9.0 nM 8.05 Fluorescent High Throughput P450 Assays: The interaction of SC12 with cytochrome... -
Cytochrome P450 2D6 IC50 = 9.0 nM 8.05 Fluorescent High Throughput P450 Assay: The interaction of SC12 with cytochrome ... -
Cytochrome P450 2D6 IC50 = 9.0 nM 8.05 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 26962886
Plasmodium falciparum EC50 = 9.59 nM 8.02 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Cytochrome P450 2D6 Ki = 9.8 nM 8.01 Inhibition of human CYP2D6 by Lineweaver-Burke plot 19117415
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of human CYP2D6 21189020
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of human CYP2D6 by fluorescence method 31693857
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of human CYP2D6 in presence of NADPH by luciferase reporter gene assa... 30615444
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibitory concentration against cytochrome P450 2D6 15481972
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of CYP2D6 after 30 mins by fluorometric assay 21138310
Cytochrome P450 2D6 IC50 = 10.0 nM 8.0 Inhibition of CYP2D6 (unknown origin) using beetle D-luciferin as substrate by C... 30568756
Cytochrome P450 2D6 IC50 = 11.0 nM 7.96 Inhibition of human CYP2D6 18324762

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1381
3681896 10.1021/jm00395a014 Canis familiaris 49
- 10.6019/CHEMBL4295262 Unchecked 40
24637077 10.1016/j.ejmech.2014.02.048 Rattus norvegicus 22
17228875 10.1021/jm060878m Heart 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
845875 10.1021/jm00213a021 Canis familiaris 13
20509610 10.1021/jm100298d NON-PROTEIN TARGET 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7205883 10.1021/jm00134a007 Canis familiaris 11
20509610 10.1021/jm100298d Molecular identity unknown 10
12699389 10.1021/jm021012t ATP-dependent translocase ABCB1 10
6167716 10.1021/jm00135a006 ADMET 10
3572966 10.1021/jm00388a005 Rattus norvegicus 10
17506538 10.1021/jm0604528 Rattus norvegicus 9
15920768 10.1002/jps.20373 ADMET 8
9927403 10.1161/01.cir.99.4.552 ATP-dependent translocase ABCB1 8
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8

Data from ChEMBL 36 via Core Engine