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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: amlodipine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
References
1. Christopoulos A, Changeux JP, Catterall WA, Fabbro D, Burris TP, Cidlowski JA, Olsen RW, Peters JA, Neubig RR, Pin JP et al.. (2014)
International union of basic and clinical pharmacology. XC. multisite pharmacology: recommendations for the nomenclature of receptor allosterism and allosteric ligands.
Pharmacol Rev, 66 (4): 918-47. [PMID:25026896]
2. Hughes AD, Wijetunge S. (1993)
The action of amlodipine on voltage-operated calcium channels in vascular smooth muscle.
Br J Pharmacol, 109 (1): 120-5. [PMID:8388295]
3. 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]