nifedipine   Click here for help

GtoPdb Ligand ID: 2514

Synonyms: Adalat® | BAY-A-1040 | Procardia®
Approved drug PDB Ligand
nifedipine is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: One of the dihydropyridine class of drugs.
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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

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View more information in the IUPHAR Pharmacology Education Project: nifedipine

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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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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 CDK toolkit. 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 107.77
Molecular weight 346.12
XLogP 3.31
No. Lipinski's rules broken 0
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.

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Canonical SMILES COC(=O)C1=C(C)NC(=C(C1c1ccccc1[N+](=O)[O-])C(=O)OC)C
Isomeric SMILES COC(=O)C1=C(C)NC(=C(C1c1ccccc1[N+](=O)[O-])C(=O)OC)C
InChI InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
InChI Key HYIMSNHJOBLJNT-UHFFFAOYSA-N
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
CYP3A4 3
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv1.2 Rn Channel blocker Pore blocker 4.7 pKd - 2
⤷ pKd 4.7 (Kd 1.8x10-5 M) [2]
Kv1.5 Hs Channel blocker - 4.1 pKd - 2
⤷ pKd 4.1 [2]
Cav1.2 Rn Gating inhibitor Antagonist 8.1 – 8.7 pIC50 - 7-8
⤷ pIC50 8.1 – 8.7 (IC50 8.9x10-9 – 2x10-9 M) 100-fold difference for nifedipine on rat smooth (pIC50 8.5) versus cardiac (pIC50 6.5) cells in vitro (Perez-Vizcaino et al. 1993). [7-8]
Voltage: -40.0 mV
Description: guinea pig, human stem cell-derived cardiomyocytes
Cav1.3 Hs Gating inhibitor Antagonist 7.7 pIC50 - 9
⤷ pIC50 7.7 (IC50 2.01x10-8 M) [9]
Description: Recombinant Cav1.3 calcium channel complexes expressed in tsA-cells
Cav1.1 Rn Gating inhibitor Antagonist 6.3 pIC50 - 5
⤷ pIC50 6.3 [5]
Voltage: -90.0 mV
Cav1.4 Hs Gating inhibitor Antagonist 6.0 pIC50 - 6
⤷ pIC50 6.0 [6]
Voltage: -100.0 mV
glycine receptor α1 subunit Hs Antagonist Antagonist 5.5 pIC50 -
⤷ pIC50 5.5 (IC50 3.3x10-6 M)
glycine receptor β subunit Hs Antagonist Antagonist 4.9 – 5.9 pIC50 -
⤷ pIC50 5.9 (IC50 1.2x10-6 M) when co-expressed with the α1 subunit
pIC50 4.9 (IC50 1.14x10-5 M) when co-expressed with the α3 subunit
Kv1.7 Mm Channel blocker - 4.9 pIC50 - 4
⤷ pIC50 4.9 [4]
glycine receptor α3 subunit Hs Antagonist Antagonist 4.5 pIC50 -
⤷ pIC50 4.5 (IC50 2.92x10-5 M)
Kv1.1 Mm Channel blocker - 4.0 pIC50 - 2
⤷ pIC50 4.0 [2]
Kv3.1 Mm Channel blocker - 3.9 pIC50 - 2
⤷ pIC50 3.9 [2]
TRPM3 Hs Activator - - - -
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Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Pregnane X receptor Hs Agonist Agonist - - - 1
⤷ [1]