isradipine   Click here for help

GtoPdb Ligand ID: 4488

Synonyms: (±)-isradipine | DynaCirc® | PN-200-110 | Prescal®
Approved drug
isradipine is an approved drug (FDA (1990))
Compound class: Synthetic organic
Comment: The approved drug isradipine is a racemic mixture of (+)-isradipine and (-)-isradipine. We show the non-stereo molecule to represent the mixture.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: isradipine

isradipine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 103.55
Molecular weight 371.15
XLogP 4.95
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)C1=C(C)NC(=C(C1c1cccc2c1non2)C(=O)OC(C)C)C
Isomeric SMILES COC(=O)C1=C(C)NC(=C(C1c1cccc2c1non2)C(=O)OC(C)C)C
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
InChI Key HMJIYCCIJYRONP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baumann L, Gerstner A, Zong X, Biel M, Wahl-Schott C. (2004)
Functional characterization of the L-type Ca2+ channel Cav1.4alpha1 from mouse retina.
Invest Ophthalmol Vis Sci, 45 (2): 708-13. [PMID:14744918]
2. Koschak A, Reimer D, Huber I, Grabner M, Glossmann H, Engel J, Striessnig J. (2001)
alpha 1D (Cav1.3) subunits can form l-type Ca2+ channels activating at negative voltages.
J Biol Chem, 276 (25): 22100-6. [PMID:11285265]
3. Koschak A, Reimer D, Walter D, Hoda JC, Heinzle T, Grabner M, Striessnig J. (2003)
Cav1.4alpha1 subunits can form slowly inactivating dihydropyridine-sensitive L-type Ca2+ channels lacking Ca2+-dependent inactivation.
J Neurosci, 23 (14): 6041-9. [PMID:12853422]
4. Ortner NJ, Bock G, Dougalis A, Kharitonova M, Duda J, Hess S, Tuluc P, Pomberger T, Stefanova N, Pitterl F et al.. (2017)
Lower Affinity of Isradipine for L-Type Ca2+ Channels during Substantia Nigra Dopamine Neuron-Like Activity: Implications for Neuroprotection in Parkinson's Disease.
J Neurosci, 37 (28): 6761-6777. [PMID:28592699]
5. Sinnegger-Brauns MJ, Hetzenauer A, Huber IG, Renström E, Wietzorrek G, Berjukov S, Cavalli M, Walter D, Koschak A, Waldschütz R et al.. (2004)
Isoform-specific regulation of mood behavior and pancreatic beta cell and cardiovascular function by L-type Ca 2+ channels.
J Clin Invest, 113 (10): 1430-9. [PMID:15146240]
6. Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J. (2009)
Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms.
Mol Pharmacol, 75 (2): 407-14. [PMID:19029287]