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Compound Detail

CHEMBL1648

ISRADIPINE
💊 Approved Drug
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💊 Approved Drug
COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc2nonc12

Basic Information

ChEMBL ID CHEMBL1648
Name ISRADIPINE
Phase Approved
Structure Type MOL
InChI Key HMJIYCCIJYRONP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Dynacirc Dynacirc cr Isradipine Isradipino Isrodipine NSC-759892 PN 200-110 PN-200-110 Prescal
11
Targets
11
Activities
2
Assay Types
7
PK Parameters
20
Publications
9
Known Names
8
Indications
1
Mechanisms

Molecular Properties

371.4
MW (Da)
2.58
ALogP
8
HBA
1
HBD
103.5
PSA (Ų)
0.82
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -dipine; -pine
USAN Year 1987

Extended Properties

Molecular Formula C19H21N3O5
MW 371.39
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.87

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 Parkinson Disease Bipolar Disorder Opioid-Related Disorders Substance-Related Disorders Smoking Cessation Tobacco Use Disorder

ATC Classification

C08CA03
isradipine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 10 meas. best 8.66
EC50 1 meas. best 6.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 8.66 8.66 2.2 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2830
IC50 6.97 6.97 107.0 1
Voltage-dependent L-type calcium channel subunit alpha-1D
CHEMBL4132
IC50 6.66 6.66 221.0 1
Onchocerca gutturosa
CHEMBL613143
EC50 6.05 6.05 890.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.44 5.44 3660.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.32 5.32 4790.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 5.3 5.3 5000.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.68 4.68 20800.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 4.55 4.55 28300.0 1
Bile salt export pump
CHEMBL6020
IC50 4.55 4.55 28000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.3 4.3 50118.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 0.197 uM.hr Homo sapiens
CL 26.0 mL.min-1.kg-1 Homo sapiens
CL 26.0 mL.min-1.kg-1 Homo sapiens
CL 300.0 mL.min-1.g-1 Homo sapiens
Fu 0.04 - Homo sapiens
MRT 1.0 hr Homo sapiens
T1/2 3.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 2.2 nM 8.66 Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in... 22761000
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 107.0 nM 6.97 Antagonist activity at rabbit voltage-dependent L-type calcium channel Cav1.2alp... 23688558
Voltage-dependent L-type calcium channel subunit alpha-1D IC50 = 221.0 nM 6.66 Antagonist activity at rat voltage-dependent L-type calcium channel Cav1.3alpha-... 23688558
Onchocerca gutturosa EC50 = 890.0 nM 6.05 AntiOnchocerca activity O. gutturosa adult males: EC50 (uM) -
Cytochrome P450 2C9 IC50 = 3660.0 nM 5.44 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate aft... 22328583
Cytochrome P450 2D6 IC50 = 4790.0 nM 5.32 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 22328583
Cytochrome P450 2C8 IC50 = 5000.0 nM 5.3 Inhibition of CYP2C8 in human liver microsomes using paclitaxel as substrate aft... 22328583
Trypanosoma cruzi IC50 = 20800.0 nM 4.68 Antitrypanosomal activity against epimastigotes of Trypanosoma cruzi 20934347
Cytochrome P450 1A2 IC50 = 28300.0 nM 4.55 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate aft... 22328583
Bile salt export pump IC50 = 28000.0 nM 4.55 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 50118.72 nM 4.3 Inhibition of human ERG 21185626

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 HEK-293T 320
- 10.6019/CHEMBL5724801 U2OS 320
- 10.6019/CHEMBL5724801 Fibroblast 320
31158845 10.1038/s41586-019-1291-3 ADMET 68
- 10.5281/zenodo.13943903 ADMET 63
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
- 10.6019/CHEMBL5303304 U2OS 7
- 10.6019/CHEMBL5303304 Fibroblast 4
18426954 10.1124/dmd.108.020479 ADMET 4
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL3832761 Onchocerca gutturosa 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 Voltage-dependent L-type calcium channel subunit alpha-1C 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine