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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View more information in the IUPHAR Pharmacology Education Project: amlodipine

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
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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
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Summary of Clinical Use Click here for help
Used in the treatment of hypertension and chronic stable angina.
Amlodipine is a component of the fixed-ratio drug Caduet® (marketed as Envacar® in some countries) which also contains the HMG-CoA inhibitor atorvastatin. Caduet® was first approved by the US FDA in 2004.
Amlodipine is also a component of Prestalia®, a mixture of amlodipine and perindopril, a drug approved (by the US FDA in 2015) for the treatment of hypertension. EMA approvals are for fixed-dose combinations of amlodipine and the AT1 receptor antagonist valsartan.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
For an overview of the mechanism of action of amlodipine, please use the DrugBank link on the Summary tab.