Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL475534

NITRENDIPINE
🧪 Phase III
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase III
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1

Basic Information

ChEMBL ID CHEMBL475534
Name NITRENDIPINE
Phase Phase III
Structure Type MOL
InChI Key PVHUJELLJLJGLN-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(+/-)-BAY-E-5009 BAY E 5009 BAY-E-5009 Bayotensin Baypress Deiten Nidrel Nitrendipine Nitrendipino Nitrepin NSC-758466
30
Targets
60
Activities
4
Assay Types
16
PK Parameters
20
Publications
11
Known Names
2
Indications
1
Mechanisms

Molecular Properties

360.4
MW (Da)
2.57
ALogP
7
HBA
1
HBD
107.8
PSA (Ų)
0.49
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

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

Extended Properties

Molecular Formula C18H20N2O6
MW 360.37
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness -0.95

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

C08CA08
nitrendipine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 42 meas. best 9.82
Ki 8 meas. best 9.61
EC50 5 meas. best 9.5
Kd 5 meas. best 9.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated L-type calcium channel
CHEMBL2095229
IC50 9.82 8.95 0.1 4
Unchecked
CHEMBL612545
Ki 9.61 9.27 0.2 3
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
Ki 9.6 9.6 0.2 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
Kd 9.59 9.59 0.3 1
ADMET
CHEMBL612558
Kd 9.59 8.4633 0.3 3
Molecular identity unknown
CHEMBL612546
EC50 9.5 8.95 0.3 2
Unchecked
CHEMBL612545
IC50 9.42 8.736 0.4 5
Oryctolagus cuniculus
CHEMBL374
IC50 9.0 9.0 1.0 1
Voltage-gated L-type calcium channel
CHEMBL2095177
IC50 8.89 8.89 1.3 1
Rattus norvegicus
CHEMBL376
IC50 8.51 8.51 3.1 1
PC-12
CHEMBL612556
IC50 8.0 8.0 10.0 1
Rattus norvegicus
CHEMBL376
EC50 7.55 7.55 28.0 1
Aorta
CHEMBL613606
EC50 7.52 7.52 30.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 6.52 6.52 300.0 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C
CHEMBL4619
IC50 5.73 5.73 1850.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.52 5.52 3000.0 1
Transient receptor potential cation channel subfamily A member 1
CHEMBL1075310
EC50 5.42 5.42 3800.0 1
Unchecked
CHEMBL612545
Kd 5.31 5.31 4897.8 1
Plasmodium falciparum
CHEMBL364
IC50 5.1 5.0 7943.3 7
Adenosine receptor A3
CHEMBL256
Ki 5.08 5.08 8300.0 1
Adenosine receptor A1
CHEMBL318
Ki 5.05 5.05 8960.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.0 5.0 10000.0 5
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.68 4.68 21100.0 1
Bile salt export pump
CHEMBL6020
IC50 4.65 4.625 22500.0 2
Adenosine receptor A2a
CHEMBL302
Ki 4.64 4.64 23000.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.57 4.57 26880.0 1
Leishmania major
CHEMBL612879
IC50 4.48 4.48 33270.0 1
Sodium channel alpha subunit
CHEMBL2331043
IC50 4.44 4.44 36000.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 4.44 4.44 36000.0 1
Leishmania amazonensis
CHEMBL612877
IC50 4.42 4.42 38320.0 1
Leishmania braziliensis
CHEMBL612878
IC50 4.41 4.41 39040.0 1
Leishmania chagasi
CHEMBL612790
IC50 4.36 4.275 43840.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 4.17 4.17 68200.0 1
Platelet-activating factor receptor
CHEMBL5136
Ki 4.13 4.13 73310.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 21.0 mL.min-1.kg-1 -
CL 16.5 mL.min-1.kg-1 Rattus norvegicus
CL 21.7 mL.min-1.kg-1 Canis lupus familiaris
CL 18.7 mL.min-1.kg-1 Homo sapiens
CL 25.0 mL.min-1.kg-1 Homo sapiens
CL 25.0 mL.min-1.kg-1 Homo sapiens
CL 166.3 mL.min-1.g-1 Homo sapiens
CL 75.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 85.0 mL.min-1.g-1 Homo sapiens
F 20.0 % Homo sapiens
Fu 0.02 - Homo sapiens
MRT 4.1 hr Homo sapiens
T1/2 0.1233 hr Canis lupus familiaris
T1/2 4.0 hr -
T1/2 8.2 hr Homo sapiens
Vd 3.8 L.kg-1 -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated L-type calcium channel IC50 = 0.15 nM 9.82 Inhibition of [3H]nitrendipine binding to L-type calcium channel of guinea pig i... 2840498
Unchecked Ki = 0.246 nM 9.61 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Voltage-dependent L-type calcium channel subunit alpha-1C Ki = 0.25 nM 9.6 Inhibition of [3H]nitrendipine binding to L-type calcium channel dihydropyridine... 2435904
Voltage-dependent L-type calcium channel subunit alpha-1C Kd = 0.26 nM 9.59 Inhibition of [3H]nitrendipine binding to L-type calcium channel in guinea pig v... 2329573
ADMET Kd = 0.26 nM 9.59 Dissociation constant for high affinity binding sites in intact cultured cardiac... 6304312
Molecular identity unknown EC50 = 0.3162 nM 9.5 Vasodilative activity in isolated Sprague-Dawley rat Superior mesenteric arteria... 26546216
Voltage-gated L-type calcium channel IC50 = 0.35 nM 9.46 Inhibition of voltage-gated L-type Ca channel (species unknown) 21300721
Unchecked IC50 = 0.383 nM 9.42 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Unchecked Ki = 0.46 nM 9.34 Displacement of [3H]Nitrendipine from L-type calcium channel dihydropyridine bin... 23403082
Unchecked IC50 = 0.72 nM 9.14 Displacement of [3H]Nitrendipine from L-type calcium channel dihydropyridine bin... 23403082
Voltage-gated L-type calcium channel IC50 = 1.0 nM 9.0 In vitro vasorelaxant activity (calcium channel blocking activity) was determine... 2391701
Oryctolagus cuniculus IC50 = 1.0 nM 9.0 Vasorelaxant potency in isolated potassium (K(+)-depolarized rabbit thoracic aor... 2329573
Voltage-gated L-type calcium channel IC50 = 1.3 nM 8.89 Inhibition of rat L-type Ca2+ channel dihydropyridine site 20875743
Unchecked Ki = 1.391 nM 8.86 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 1.565 nM 8.8 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 3.0 nM 8.52 Inhibition of human voltage-dependent L-type calcium channel subunit alpha1C/alp... 22694270
Rattus norvegicus IC50 = 3.1 nM 8.51 Dose-dependent inhibition of calcium contraction in depolarized rat aortic strip... 2435904
Molecular identity unknown EC50 = 3.981 nM 8.4 Vasodilative activity in isolated Sprague-Dawley rat mesenteric arterial ring as... 25466182
PC-12 IC50 = 10.0 nM 8.0 Ability to block depolarization induced 45Ca uptake into pheochromocytoma PC12 c... 6304312
ADMET Kd = 10.0 nM 8.0 Dissociation constant for binding to isolated membranes from clonal cell line 6304312

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 523
31158845 10.1038/s41586-019-1291-3 ADMET 344
- 10.5281/zenodo.13943903 ADMET 59
- 10.6019/CHEMBL4295262 Unchecked 44
31158845 10.1038/s41586-019-1291-3 Nitroreductase domain-containing protein 25
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
3172124 10.1021/jm00118a004 Cavia porcellus 10
2299629 10.1021/jm00164a028 Homo sapiens 10
- 10.6019/CHEMBL5303304 U2OS 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
11602674 - ATP-dependent translocase ABCB1 8
31158845 10.1038/s41586-019-1291-3 Diguanylate cyclase 7
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
2299629 10.1021/jm00164a028 Rattus norvegicus 6
31158845 10.1038/s41586-019-1291-3 NADH dehydrogenase/NAD(P)H nitroreductase 6
- 10.1007/s00044-010-9477-0 Rattus norvegicus 6
- 10.6019/CHEMBL5303304 HEK-293T 5
31158845 10.1038/s41586-019-1291-3 Nitroreductase-like protein 5
- 10.6019/CHEMBL3301361 ADMET 5
20451399 10.1016/j.bmc.2010.04.027 Aorta 4

Data from ChEMBL 36 via Core Engine