ISRADIPINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1990)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C08CA03
UNII: YO1UK1S598

Structure
InChI Key HMJIYCCIJYRONP-UHFFFAOYSA-N
Smile COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc2nonc12
InChI
InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H21N3O5
Molecular Weight 371.39
AlogP 2.58
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 103.55
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0

Pharmacology

Action Mechanism of Action Reference
BLOCKER Voltage-gated L-type calcium channel blocker
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 28300 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 5000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 3660 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 4790 - - -
Enzyme Hydrolase
- - - - 0.6075
Enzyme Transferase
- - - - 5.45
Enzyme
- 28300 - - 0.6075
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -0.75-21.86
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 50118.72 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 107 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 12
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 28000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension 4 D006973 ClinicalTrials
Parkinson Disease 3 D010300 ClinicalTrials
Bipolar Disorder 2 D001714 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Smoking Cessation 1 D016540 ClinicalTrials
Tobacco Use Disorder 1 D014029 ClinicalTrials
Opioid-Related Disorders 1 D009293 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache
Nervous system disorders Headache 13.7
Nervous system disorders Headache 9.4
Cardiac disorders Dizziness 8.2
Cardiac disorders Dizziness 7.3
General disorders and administration site conditions Oedema 7.2
General disorders and administration site conditions Asthenia 6.3
General disorders and administration site conditions Fatigue 6.3
Cardiac disorders Dizziness
Cardiac disorders Palpitations 4.0
Gastrointestinal disorders Abdominal discomfort 3.9
General disorders and administration site conditions Asthenia 3.9
General disorders and administration site conditions Fatigue 3.9
Gastrointestinal disorders Nausea 3.1
General disorders and administration site conditions Oedema
Cardiac disorders Chest pain 2.9
General disorders and administration site conditions Oedema 2.9
General disorders and administration site conditions Flushing 2.6
Cardiac disorders Chest pain
Cardiac disorders Chest pain 2.4
Cardiac disorders Dyspnoea 2.2
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 1.9
Cardiac disorders Dyspnoea 1.8
Gastrointestinal disorders Nausea 1.8
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Abdominal discomfort 1.7
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Dermatitis 1.5
Cardiac disorders Palpitations 1.5
Renal and urinary disorders Pollakiuria 1.5
Skin and subcutaneous tissue disorders Rash 1.5
Cardiac disorders Tachycardia 1.5
Cardiac disorders Palpitations
General disorders and administration site conditions Asthenia 1.2
General disorders and administration site conditions Flushing 1.2
Gastrointestinal disorders Diarrhoea 1.1
Gastrointestinal disorders Vomiting 1.1
Cardiac disorders Dyspnoea
Renal and urinary disorders Pollakiuria 1.0
Skin and subcutaneous tissue disorders Dermatitis 0.7
Skin and subcutaneous tissue disorders Rash 0.7
Cardiac disorders Tachycardia 0.5
General disorders and administration site conditions Asthenia
Skin and subcutaneous tissue disorders Dermatitis
General disorders and administration site conditions Fatigue
Skin and subcutaneous tissue disorders Rash
Cardiac disorders Tachycardia
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
33.33
Cardiac disorders
21.21
Respiratory, thoracic and mediastinal disorders
9.09
Vascular disorders
9.09
Immune system disorders
6.06
Injury, poisoning and procedural complications
6.06
Investigations
6.06
Gastrointestinal disorders
3.03
Nervous system disorders
3.03
Psychiatric disorders
3.03

Cross References

Resources Reference
CAS NUMBER 75695-93-1
ChEBI 6073
ChEMBL CHEMBL1648
DrugBank DB00270
DrugCentral 1511
EPA CompTox DTXSID4023179
FDA SRS YO1UK1S598
Human Metabolome Database HMDB14415
Guide to Pharmacology 4488
KEGG D00349
PharmGKB PA450131
PubChem 3784
SureChEMBL SCHEMBL34555
ZINC ZINC22001248
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