amlodipine   Click here for help

GtoPdb Ligand ID: 6981

Synonyms: amlodipine besylate | amlodipine maleate | Copalia® (amlodipine + valsartan) | Katerzia® (amlodipine oral suspension, 1 mg/mL) | Norvasc® | UK-4834011
Approved drug
amlodipine is an approved drug (FDA (1992), EMA (2007))
Compound class: Synthetic organic
Comment: Amlodipine is a long-acting dihydropyridine class calcium channel blocker.
Amlodipine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 99.88
Molecular weight 408.15
XLogP 3.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCCOCC1=C(C(=O)OCC)C(C(=C(N1)C)C(=O)OC)c1ccccc1Cl
Isomeric SMILES NCCOCC1=C(C(=O)OCC)C(C(=C(N1)C)C(=O)OC)c1ccccc1Cl
InChI InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3
InChI Key HTIQEAQVCYTUBX-UHFFFAOYSA-N
Bioactivity Comments
Due to the complex nature of this drug's MMOA, and the paucity of (human) affinity data, we do not tag a primary drug target.

Amlodipine has been described as a gating modifier of Cav channels [1].
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Cav1.2 Oc Gating inhibitor - 9.3 pIC50 - 2
pIC50 9.3 [2]
Description: Determined in vascular smooth muscle.
Cav1.3 Hs Gating inhibitor Inhibition 7.2 pIC50 - 3
pIC50 7.2 (IC50 6.01x10-8 M) [3]
Description: Recombinant Cav1.3 calcium channel complexes expressed in tsA-cells