nifedipine   

GtoPdb Ligand ID: 2514

Synonyms: Adalat® | BAY-A-1040 | Procardia®
nifedipine is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: One of the dihydropyridine class of drugs.
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2D Structure
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Physico-chemical Properties
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
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 7.7 pIC50 - 7-8
pIC50 7.7 There was a 100-fold difference for nifedipine on smooth (pIC50 8.5) versus cardiac (pIC50 6.5) cells in vitro (Perez-Vizcaino et al. 1993). [7-8]
Voltage: -80.0 mV
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 1x10-7 - 1x10-4 5
pIC50 6.3 Conc range: 1x10-7 - 1x10-4 M [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 - - - -
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Pregnane X receptor Hs Agonist Agonist - - - 1
[1]