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Compound Detail

CHEMBL1726

NISOLDIPINE
💊 Approved Drug
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💊 Approved Drug
COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1c1ccccc1[N+](=O)[O-]

Basic Information

ChEMBL ID CHEMBL1726
Name NISOLDIPINE
Phase Approved
Structure Type MOL
InChI Key VKQFCGNPDRICFG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BAY K 5552 BAY-K-5552 Baymycard Geomatrix 16e Nisocor Nisoldipin Nisoldipine Nisoldipine (stn) Nisoldipino NSC-759106 Sular Syscor mr 10 +2 more
14
Targets
25
Activities
4
Assay Types
15
PK Parameters
20
Publications
14
Known Names
2
Indications
1
Mechanisms

Molecular Properties

388.4
MW (Da)
3.20
ALogP
7
HBA
1
HBD
107.8
PSA (Ų)
0.45
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -dipine; -pine
USAN Year 1981

Extended Properties

Molecular Formula C20H24N2O6
MW 388.42
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness -0.75

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Voltage-gated L-type calcium channel blocker BLOCKER Voltage-gated L-type calcium channel

Indications

Cardiovascular Diseases Hypertension

ATC Classification

C08CA07
nisoldipine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 15 meas. best 9.13
Ki 5 meas. best 9.32
EC50 4 meas. best 5.1
Kd 1 meas. best 7.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.32 7.7167 0.5 3
Unchecked
CHEMBL612545
IC50 9.13 7.6233 0.7 3
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 8.52 8.52 3.0 1
Rattus norvegicus
CHEMBL376
Kd 7.75 7.75 18.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
IC50 7.1 6.62 80.0 2
Cytochrome P450 1A2
CHEMBL3356
IC50 6.0 6.0 1000.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.64 5.64 2278.0 1
Adenosine receptor A2a
CHEMBL251
IC50 5.39 5.39 4058.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.39 5.39 4024.0 1
Adenosine receptor A3
CHEMBL256
IC50 5.15 5.15 7120.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 5.1 5.0 7900.0 3
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.78 4.78 16500.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.64 4.64 23000.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 4.58 4.58 26000.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL2146315
EC50 4.5 4.5 31600.0 1
Bile salt export pump
CHEMBL6020
IC50 4.48 4.48 33000.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 4.36 4.36 44100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 52.05 ng.hr.mL-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 300.0 mL.min-1.g-1 Homo sapiens
Cmax 12.9 nM Homo sapiens
Excretion 60.0 % Homo sapiens
F 5.0 % Homo sapiens
Fu 0.003 - Homo sapiens
Fu 0.003 - Homo sapiens
MRT 6.5 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 13.7 hr Homo sapiens
Tmax 9.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.476 nM 9.32 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Unchecked IC50 = 0.741 nM 9.13 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Unchecked Ki = 2.208 nM 8.66 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 2.484 nM 8.61 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 3.0 nM 8.52 Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in... 22761000
Rattus norvegicus Kd = 18.0 nM 7.75 Equilibrium dissociation constant based on membrane concentration in rat smooth ... 2002467
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 80.0 nM 7.1 Inhibition of L-type calcium channel measured using whole-cell patch clamp in gu... 22761000
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 730.0 nM 6.14 Inhibition of L-type calcium channel measured using whole-cell patch clamp in gu... 22761000
Cytochrome P450 1A2 IC50 = 1000.0 nM 6.0 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Adenosine receptor A2a Ki = 2278.0 nM 5.64 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -
Adenosine receptor A3 Ki = 4024.0 nM 5.39 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Adenosine receptor A2a IC50 = 4058.0 nM 5.39 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -
Unchecked Ki = 6709.0 nM 5.17 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Adenosine receptor A3 IC50 = 7120.0 nM 5.15 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Unchecked IC50 = 7354.0 nM 5.13 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Nuclear receptor subfamily 1 group I member 2 EC50 = 7900.0 nM 5.1 Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay 20966043
Nuclear receptor subfamily 1 group I member 2 EC50 = 10000.0 nM 5.0 Activation of human PXR expressed in human HepG2 (DPX-2) cells after 24 hrs by l... 20966043
Nuclear receptor subfamily 1 group I member 2 EC50 = 12600.0 nM 4.9 Activation of human PXR expressed in human HepG2 (DPX-2) cells assessed as induc... 20966043
ATP-binding cassette sub-family C member 4 IC50 = 16500.0 nM 4.78 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 23000.0 nM 4.64 Inhibitory concentration against IKr potassium channel 15324906

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 428
16472241 10.2174/1570163043334794 Hepatotoxicity 18
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
16019946 10.1080/00498250400028197 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
22761000 10.1002/jat.2784 Voltage-dependent L-type calcium channel subunit alpha-1C 3
20014752 10.1021/tx900326k Hepatotoxicity 3
23956101 10.1093/toxsci/kft176 Unchecked 2
22931300 10.1021/tx300075j Liver microsomes 2
25036789 10.1016/j.ejmech.2014.06.078 Indoleamine 2,3-dioxygenase 1 2
24799086 10.1002/hep.27206 Homo sapiens 2
19445515 10.1021/jm900403j Homo sapiens 2
2002467 10.1021/jm00107a001 Rattus norvegicus 2
- 10.6019/CHEMBL3301361 No relevant target 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2

Data from ChEMBL 36 via Core Engine