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Compound Detail

CHEMBL1428

NIMODIPINE
💊 Approved Drug
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💊 Approved Drug
COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1

Basic Information

ChEMBL ID CHEMBL1428
Name NIMODIPINE
Phase Approved
Structure Type MOL
InChI Key UIAGMCDKSXEBJQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Admon BAY E 9736 BAY-E-9736 Nemotan Nimodipine Nimodipine ap Nimodipino Nimotop NSC-758476 Nymalize Periplum
32
Targets
51
Activities
4
Assay Types
25
PK Parameters
20
Publications
11
Known Names
11
Indications
2
Mechanisms

Molecular Properties

418.4
MW (Da)
2.97
ALogP
8
HBA
1
HBD
117.0
PSA (Ų)
0.30
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1988
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -dipine; -pine
USAN Year 1979

Extended Properties

Molecular Formula C21H26N2O7
MW 418.45
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness -1.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mineralocorticoid receptor antagonist ANTAGONIST Mineralocorticoid receptor
Voltage-gated L-type calcium channel blocker BLOCKER Voltage-gated L-type calcium channel

Indications

Cardiovascular Diseases Poisoning Subarachnoid Hemorrhage Cocaine-Related Disorders Infertility Muscle Cramp Neuroma, Acoustic Stroke Intracranial Aneurysm Cerebrovascular Disorders Schizophrenia

ATC Classification

C08CA06
nimodipine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CALCIUM CHANNEL BLOCKERS

Drug Warnings

Black Box Warning
misuse
Country: United States

Activity Summary

IC50 39 meas. best 9.62
Ki 7 meas. best 9.81
EC50 4 meas. best 6.41
Kd 1 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.81 8.3 0.2 3
Unchecked
CHEMBL612545
IC50 9.62 8.075 0.2 4
Cavia porcellus
CHEMBL369
IC50 7.83 7.83 14.9 1
L-type calcium channel alpha-1c/beta-2/alpha2delta-1
CHEMBL4106164
IC50 7.53 7.53 29.8 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 6.96 6.96 110.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
IC50 6.52 6.52 300.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 6.41 6.41 390.0 1
Unchecked
CHEMBL612545
EC50 6.28 6.28 520.0 1
Rattus norvegicus
CHEMBL376
Kd 6.16 6.16 690.0 1
Transient receptor potential cation channel subfamily A member 1
CHEMBL1075310
EC50 6.1 6.1 800.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 6.0 5.885 1000.0 2
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C
CHEMBL4619
IC50 5.91 5.91 1243.0 2
Cannabinoid receptor 1
CHEMBL218
Ki 5.86 5.86 1371.0 1
Cannabinoid receptor 1
CHEMBL218
IC50 5.76 5.76 1736.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.75 5.75 1780.0 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A
CHEMBL3421
IC50 5.7 5.7 2000.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.66 5.53 2170.0 2
Cytochrome P450 2J2
CHEMBL3491
IC50 5.47 5.47 3380.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.3 5.0571 5011.9 7
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
IC50 5.15 5.15 7150.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.14 5.14 7200.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.07 5.07 8470.0 1
Bile acid receptor
CHEMBL2047
IC50 5.05 5.05 8960.0 1
Bile salt export pump
CHEMBL6020
IC50 5.0 5.0 10100.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.86 4.86 13700.0 1
Voltage-gated calcium channel
CHEMBL2363032
IC50 4.85 4.85 14000.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 4.74 4.74 18300.0 1
Adenosine receptor A1
CHEMBL318
Ki 4.7 4.7 20100.0 1
Leishmania chagasi
CHEMBL612790
IC50 4.67 4.375 21620.0 2
Leishmania major
CHEMBL612879
IC50 4.51 4.51 31040.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.49 4.49 32310.0 1
Leishmania braziliensis
CHEMBL612878
IC50 4.37 4.37 42800.0 1
Adenosine receptor A2a
CHEMBL302
Ki 4.35 4.35 44300.0 1
LLC-MK2
CHEMBL614691
IC50 4.02 4.02 96190.0 1
PC-12
CHEMBL612556
EC50 4.01 4.01 97300.0 1

Pharmacokinetic Data

Parameter Value Units Species
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 56.0 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 33.0 mL.min-1.kg-1 Macaca
CL 34.0 mL.min-1.kg-1 Canis lupus familiaris
CL 300.0 mL.min-1.g-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
Cmax 195.0 nM Homo sapiens
F 20.0 % Homo sapiens
F 13.0 % Homo sapiens
Fu 0.016 - Homo sapiens
Fu 0.016 - Homo sapiens
Fu 0.008 - Homo sapiens
Fu 0.009 - Macaca fascicularis
Fu 0.007 - Canis lupus familiaris
Fu 0.007 - Cavia porcellus
Fu 0.007 - Mus musculus
Fu 0.009 - Rattus norvegicus
Fu 0.01 - Rattus norvegicus
MRT 1.2 hr Homo sapiens
T1/2 1.3 hr Homo sapiens
T1/2 1.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.156 nM 9.81 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Unchecked IC50 = 0.242 nM 9.62 DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:... -
Unchecked Ki = 1.86 nM 8.73 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 2.093 nM 8.68 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 8.0 nM 8.1 Inhibition of voltage-gated calcium channel in Wistar rat synaptoneurosomes afte... 26832222
Cavia porcellus IC50 = 14.9 nM 7.83 Calcium channel antagonist activity against carbachol-induced contractile respon... 8917646
L-type calcium channel alpha-1c/beta-2/alpha2delta-1 IC50 = 29.8 nM 7.53 Inhibition of human alpha1c/beta2a/alpha2delta1 Cav1.2 expressed in HEK293 cells... 35666471
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 110.0 nM 6.96 Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in... 22761000
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 300.0 nM 6.52 Inhibition of L-type calcium channel measured using whole-cell patch clamp in gu... 22761000
Nuclear receptor subfamily 1 group I member 2 EC50 = 390.0 nM 6.41 Agonist activity at PXR (unknown origin) expressed in human HepG2 cells assessed... 23688559
Unchecked Ki = 433.0 nM 6.36 DRUGMATRIX: Sodium/nucleoside co-transporter radioligand binding (ligand: nitrob... -
Unchecked EC50 = 520.0 nM 6.28 Antagonist activity at New Zealand rabbit L-type calcium channel assessed as dil... 28720331
Rattus norvegicus Kd = 690.0 nM 6.16 Equilibrium dissociation constant based on membrane concentration in rat smooth ... 2002467
Transient receptor potential cation channel subfamily A member 1 EC50 = 800.0 nM 6.1 Agonist activity at mouse TRPA1 channel expressed in CHO cells assessed as incre... 20356305
Cytochrome P450 2C9 IC50 = 1000.0 nM 6.0 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C IC50 = 1243.0 nM 5.91 Inhibition of PDE1C (147 to 531 residues) (unknown origin) expressed in Escheric... 35666471
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C IC50 = 1243.0 nM 5.91 Inhibition of PDE1C (unknown origin) 38000211
Unchecked IC50 = 1266.0 nM 5.9 DRUGMATRIX: Sodium/nucleoside co-transporter radioligand binding (ligand: nitrob... -
Cannabinoid receptor 1 Ki = 1371.0 nM 5.86 DRUGMATRIX: Cannabinoid CB1 radioligand binding (ligand: [3H] SR141716A) -
Cytochrome P450 2C9 IC50 = 1690.0 nM 5.77 Inhibition of CYP2C9 in human liver microsomes using tolbutamide substrate by LC... 23033255

Literature References

Data from ChEMBL 36 via Core Engine