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Compound Detail

CHEMBL640

PROCAINAMIDE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCNC(=O)c1ccc(N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL640
Name PROCAINAMIDE
Phase Approved
Structure Type MOL
InChI Key REQCZEXYDRLIBE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Novocainamide NSC-27461 Procainamida Procainamide Sp 100 (pharmaceutical)
8
Targets
27
Activities
3
Assay Types
17
PK Parameters
20
Publications
5
Known Names
6
Indications

Molecular Properties

235.3
MW (Da)
1.34
ALogP
3
HBA
2
HBD
58.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C13H21N3O
MW 235.33
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -1.40

Indications

Arrhythmias, Cardiac Atrial Fibrillation Death, Sudden, Cardiac Heart Failure Myocardial Infarction Ventricular Fibrillation

ATC Classification

C01BA02
procainamide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

IC50 16 meas. best 6.3
Ki 9 meas. best 6.0
EC50 2 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.85 7.85 14.0 2
Acetylcholinesterase
CHEMBL4768
 IC50 6.3 6.3 500.0 1
Acetylcholinesterase
CHEMBL220
 IC50 6.0 6.0 1000.0 2
Acetylcholinesterase
CHEMBL220
 Ki 6.0 6.0 1000.0 2
Acetylcholinesterase
CHEMBL4768
 Ki 6.0 6.0 1000.0 1
Solute carrier family 22 member 1
CHEMBL2073664
 IC50 5.41 5.41 3900.0 1
Solute carrier family 22 member 1
CHEMBL2073670
 IC50 5.16 5.0633 7000.0 3
Solute carrier family 22 member 1
CHEMBL2073670
 Ki 4.89 4.61 13000.0 2
Solute carrier family 22 member 2
CHEMBL1770032
 Ki 4.44 4.44 36000.0 1
Solute carrier family 22 member 2
CHEMBL1743122
 Ki 4.3 4.3 50000.0 1
Solute carrier family 22 member 1
CHEMBL5685
 Ki 4.13 4.13 73900.0 1
Solute carrier family 22 member 2
CHEMBL1770032
 IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 10.0 mL.min-1.kg-1 Homo sapiens
CL 5.5 mL.min-1.kg-1 Homo sapiens
CL 10.0 mL.min-1.kg-1 Homo sapiens
CL 10.0 mL.min-1.kg-1 Homo sapiens
CL 0.000413 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 0.413 uL/min Homo sapiens
F 79.0 % Homo sapiens
F 83.0 % Homo sapiens
Fu 0.84 - -
Fu 0.186 - -
Fu 0.84 - Homo sapiens
Fu 0.84 - Homo sapiens
Fu 0.84 - Homo sapiens
MRT 3.7 hr Homo sapiens
T1/2 3.1 hr Homo sapiens
T1/2 3.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET EC50 = 14.0 nM 7.85 Negative inotropic activity against potassium-induced contraction in guinea pig ... 20509610
NON-PROTEIN TARGET EC50 = 14.0 nM 7.85 Negative inotropic activity assessed as decrease in developed tension in isolate... 17228875
Acetylcholinesterase IC50 = 500.0 nM 6.3 Inhibition of Acetylcholinesterase activity of calf forebrain 9301662
Acetylcholinesterase IC50 = 1000.0 nM 6.0 Inhibition of Acetylcholinesterase from human red blood cells 9301662
Acetylcholinesterase IC50 = 1000.0 nM 6.0 Inhibition of Acetylcholinesterase activity from octopus brain 9301662
Acetylcholinesterase Ki = 1000.0 nM 6.0 Binding affinity against Acetylcholinesterase of purified Octopus brain (OB) 9301662
Acetylcholinesterase Ki = 1000.0 nM 6.0 Binding affinity against Acetylcholinesterase of human RBC 9301662
Acetylcholinesterase Ki = 1000.0 nM 6.0 Binding affinity against Acetylcholinesterase of purified calf forebrain (CFB) 9301662
Solute carrier family 22 member 1 IC50 = 3900.0 nM 5.41 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 1 uM) in Xenopus laevis oocytes 12176030
Solute carrier family 22 member 1 IC50 = 7000.0 nM 5.16 TP_TRANSPORTER: inhibition of TEA uptake (in the presence of bicarbonate) (TEA: ... 12438515
Solute carrier family 22 member 1 IC50 = 7700.0 nM 5.11 TP_TRANSPORTER: inhibition pramipexole uptake in rOCT1-injected oocytes 15640376
Solute carrier family 22 member 1 IC50 = 12000.0 nM 4.92 TP_TRANSPORTER: inhibition of TEA uptake (in the absence of bicarbonate) (TEA: 2... 12438515
Solute carrier family 22 member 1 Ki = 13000.0 nM 4.89 TP_TRANSPORTER: inhibition of TEA uptake in Xenopus laevis oocytes 7990927
Solute carrier family 22 member 2 Ki = 36000.0 nM 4.44 TP_TRANSPORTER: inhibition of TEA uptake in OCT2-expressing MDCK cells 11758759
Solute carrier family 22 member 1 Ki = 47000.0 nM 4.33 TP_TRANSPORTER: inhibition of TEA uptake in OCT1-expressing MDCK cells 11758759
Solute carrier family 22 member 2 Ki = 50000.0 nM 4.3 TP_TRANSPORTER: inhibition of TEA uptake in Xenopus laevis oocytes 9260930
Solute carrier family 22 member 1 Ki = 73900.0 nM 4.13 TP_TRANSPORTER: inhibition of TEA uptake in OCT1-expressing HeLa cells 9655880
Solute carrier family 22 member 2 IC50 = 90000.0 nM 4.05 TP_TRANSPORTER: inhibition of TEA uptake (in the presence of bicarbonate) (TEA: ... 12438515

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 224
3385724 10.1021/jm00402a006 Canis familiaris 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2918518 10.1021/jm00123a033 Canis familiaris 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
845875 10.1021/jm00213a021 Canis familiaris 10
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
9301662 10.1021/jm970141k Acetylcholinesterase 6
12061889 10.1021/jm0200409 ADMET 5
3385724 10.1021/jm00402a006 Rattus norvegicus 5
18426954 10.1124/dmd.108.020479 ADMET 4
20509610 10.1021/jm100298d NON-PROTEIN TARGET 4
17228875 10.1021/jm060878m NON-PROTEIN TARGET 3
20014752 10.1021/tx900326k Hepatotoxicity 3
3385724 10.1021/jm00402a006 Unchecked 3
21467212 10.1124/dmd.111.039180 Liver microsome 3
- 10.6019/CHEMBL3301361 No relevant target 3
24249037 10.1007/s11095-013-1232-z No relevant target 3

Data from ChEMBL 36 via Core Engine