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Compound Detail

CHEMBL517

DISOPYRAMIDE
💊 Approved Drug
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💊 Approved Drug
CC(C)N(CCC(C(N)=O)(c1ccccc1)c1ccccn1)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL517
Name DISOPYRAMIDE
Phase Approved
Structure Type MOL
InChI Key UVTNFZQICZKOEM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(rs)-disopyramide Dicorantil Disopiramida Disopyramide Dl-disopyramide H-3292 Isorythm Lispine Ritmilen Rythmodan p SC-7031 Searle-703
8
Targets
15
Activities
3
Assay Types
16
PK Parameters
20
Publications
12
Known Names
3
Indications

Molecular Properties

339.5
MW (Da)
3.36
ALogP
3
HBA
1
HBD
59.2
PSA (Ų)
0.80
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C21H29N3O
MW 339.48
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.74

Indications

Arrhythmias, Cardiac Atrial Fibrillation Heart Failure

ATC Classification

C01BA03
disopyramide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

IC50 11 meas. best 5.82
Kd 2 meas. best 6.44
Ki 2 meas. best 4.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cavia porcellus
CHEMBL369
 Kd 6.44 6.245 363.1 2
Cavia porcellus
CHEMBL369
 IC50 5.82 5.82 1500.0 1
Solute carrier family 22 member 2
CHEMBL1743122
 IC50 5.54 5.54 2900.0 1
Unchecked
CHEMBL612545
 IC50 5.41 5.41 3900.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.92 4.216 12000.0 5
Solute carrier family 22 member 2
CHEMBL1770032
 Ki 4.52 4.52 30000.0 1
Solute carrier family 22 member 1
CHEMBL2073670
 Ki 4.21 4.21 62000.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
 IC50 4.18 4.18 66000.0 1
Solute carrier family 22 member 1
CHEMBL5685
 IC50 4.09 4.09 81700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.9 mL.min-1.kg-1 Homo sapiens
CL 0.4 mL.min-1.kg-1 Homo sapiens
CL 0.9 mL.min-1.kg-1 Homo sapiens
CL 0.9 mL.min-1.kg-1 Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Macaca
CL 29.0 mL.min-1.kg-1 Canis lupus familiaris
CL 34.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 7950.0 nM Homo sapiens
F 80.0 % Homo sapiens
Fu 0.16 - Homo sapiens
Fu 0.16 - Homo sapiens
Fu 0.669 - Rattus norvegicus
Fu 0.491 - Rattus norvegicus
MRT 9.6 hr Homo sapiens
T1/2 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cavia porcellus Kd = 363.08 nM 6.44 Anticholinergic activity is assessed in guinea pig ileum at 3 uM 6384519
Cavia porcellus Kd = 891.25 nM 6.05 Antimuscarinic activity in guinea pig ileum 4032431
Cavia porcellus IC50 = 1500.0 nM 5.82 Inhibitory concentration of guinea pig ileum longitudinal muscle strips to antag... 7241519
Solute carrier family 22 member 2 IC50 = 2900.0 nM 5.54 Inhibition of human OCT2 expressed in HEK-293-Flp-In cells incubated for 3 mins ... 21599003
Unchecked IC50 = 3900.0 nM 5.41 Inhibition of human OCT2 A270S mutant expressed in HEK-293-Flp-In cells incubate... 21599003
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 12000.0 nM 4.92 Inhibitory concentration against IKr potassium channel 15324906
Solute carrier family 22 member 2 Ki = 30000.0 nM 4.52 TP_TRANSPORTER: inhibition of TEA uptake in OCT2-expressing MDCK cells 11758759
Solute carrier family 22 member 1 Ki = 62000.0 nM 4.21 TP_TRANSPORTER: inhibition of TEA uptake in OCT1-expressing MDCK cells 11758759
Multidrug and toxin extrusion protein 1 IC50 = 66000.0 nM 4.18 Inhibition of human MATE1 expressed in HEK-293-Flp-In cells incubated for 3 mins... 21599003
Solute carrier family 22 member 1 IC50 = 81700.0 nM 4.09 Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT... 18788725
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 91201.08 nM 4.04 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 91201.08 nM 4.04 Inhibitory concentration against potassium channel HERG 15911273
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 91201.08 nM 4.04 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 91201.08 nM 4.04 Inhibition of human ERG 21185626

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1384
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 57
- 10.6019/CHEMBL4295262 Unchecked 44
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
15920768 10.1002/jps.20373 ADMET 8
7205883 10.1021/jm00134a007 Canis familiaris 8
7420355 10.1021/jm00184a008 Canis familiaris 7
6147415 10.1021/jm00375a010 Canis familiaris 6
6147415 10.1021/jm00375a010 Mus musculus 5
21599003 10.1021/jm2001629 ADMET 5
4032431 10.1021/jm00147a029 Canis familiaris 4
1992110 10.1021/jm00105a003 Canis familiaris 4
18426954 10.1124/dmd.108.020479 ADMET 4
33619967 10.1021/acs.jmedchem.0c02011 ADMET 4
16019946 10.1080/00498250400028197 ADMET 4

Data from ChEMBL 36 via Core Engine