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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1992), EMA (2007))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
O3-ethyl O5-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
International Nonproprietary Names Click here for help
INN number INN
5729 amlodipine
Synonyms Click here for help
amlodipine besylate | amlodipine maleate | Copalia® (amlodipine + valsartan) | Katerzia® (amlodipine oral suspension, 1 mg/mL) | Norvasc® | UK-4834011
Database Links Click here for help
CAS Registry No. 88150-42-9 (source: Scifinder)
ChEMBL Ligand CHEMBL1491
DrugBank Ligand DB00381
DrugCentral Ligand 183
GtoPdb PubChem SID 178103560
PubChem CID 2162
Search Google for chemical match using the InChIKey HTIQEAQVCYTUBX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HTIQEAQVCYTUBX
Search PubMed clinical trials amlodipine
Search PubMed titles amlodipine
Search PubMed titles/abstracts amlodipine
UniChem Compound Search for chemical match using the InChIKey HTIQEAQVCYTUBX-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HTIQEAQVCYTUBX-UHFFFAOYSA-N
Wikipedia Amlodipine