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Compound Detail

CHEMBL652

FLECAINIDE
💊 Approved Drug
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💊 Approved Drug
O=C(NCC1CCCCN1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL652
Name FLECAINIDE
Phase Approved
Structure Type MOL
InChI Key DJBNUMBKLMJRSA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Flecainida Flecainide FLECAINIDE COMPONENT OF THN-102 Flecainide component of thn102 NSC-719273
5
Targets
10
Activities
1
Assay Types
14
PK Parameters
20
Publications
5
Known Names
3
Indications

Molecular Properties

414.4
MW (Da)
3.44
ALogP
4
HBA
2
HBD
59.6
PSA (Ų)
0.67
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning
USAN Year 1977

Extended Properties

Molecular Formula C17H20F6N2O3
MW 414.35
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness -0.90

Indications

Arrhythmias, Cardiac Atrial Fibrillation Arrhythmogenic Right Ventricular Dysplasia

ATC Classification

C01BC04
flecainide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

IC50 10 meas. best 5.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.41 5.41 3890.4 4
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 5.19 5.19 6500.0 1
A-type voltage-gated potassium channel KCND2
CHEMBL1075227
 IC50 5.0 5.0 10100.0 1
Voltage-gated L-type calcium channel
CHEMBL2095229
 IC50 4.57 4.57 27100.0 1
Potassium voltage-gated channel subfamily A member 5
CHEMBL4306
 IC50 4.29 4.29 51000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.39 - -
Fu 0.031 - -
Fu 0.39 - Homo sapiens
Fu 0.52 - Homo sapiens
Fu 0.52 - Homo sapiens
MRT 21.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3890.45 nM 5.41 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3890.45 nM 5.41 Inhibitory concentration against potassium channel HERG 15911273
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3890.45 nM 5.41 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3890.45 nM 5.41 Inhibition of human ERG 21185626
Sodium channel protein type 5 subunit alpha IC50 = 6500.0 nM 5.19 Inhibition of human heart sodium channel Nav1.5 by patch-clamp method 17506538
A-type voltage-gated potassium channel KCND2 IC50 = 10100.0 nM 5.0 Inhibition of rat potassium channel Kv4.2 by patch-clamp method 17506538
Voltage-gated L-type calcium channel IC50 = 27100.0 nM 4.57 Inhibition of Cav1.2 current measured using QPatch automatic path clamp system i... 23812503
Potassium voltage-gated channel subfamily A member 5 IC50 = 51000.0 nM 4.29 Inhibition of human potassium channel Kv1.5 by patch-clamp method 17506538

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17506538 10.1021/jm0604528 Rattus norvegicus 7
2299628 10.1021/jm00164a025 Canis familiaris 6
12061889 10.1021/jm0200409 ADMET 5
- 10.6019/CHEMBL3301361 ADMET 5
2299628 10.1021/jm00164a025 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
8230126 10.1021/jm00074a017 Cavia porcellus 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3

Data from ChEMBL 36 via Core Engine