Amlodipine besylate

Amlodipine

Clinical data
Pronunciation	/æmˈloʊdəˌpin/
Trade names	Norvasc, others
AHFS/Drugs.com	Monograph
MedlinePlus	a692044
License data	EU EMA: by INN US DailyMed: Amlodipine US FDA: Amlodipine
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	C08CA01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	64–90%
Protein binding	93%
Metabolism	Liver
Metabolites	Various inactive pyrimidine metabolites
Onset of action	Highest availability 6–12 hours after oral dose
Biological half-life	30–50 hours
Duration of action	At least 24 hours
Excretion	Urine
Identifiers
IUPAC name (RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number	88150-42-9 Y
PubChem CID	2162
IUPHAR/BPS	6981
DrugBank	DB00381 Y
ChemSpider	2077 Y
UNII	1J444QC288
KEGG	D07450 Y
ChEBI	CHEBI:2668 Y
ChEMBL	CHEMBL1491 Y
PDB ligand	6UB (PDBe, RCSB PDB)
ECHA InfoCard	100.102.428
Chemical and physical data
Formula	C20H25ClN2O5
Molar mass	408.879 g/mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES Clc1ccccc1C2C(=C(/N/C(=C2/C(=O)OCC)COCCN)C)\C(=O)OC
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 Y Key:HTIQEAQVCYTUBX-UHFFFAOYSA-N Y

Amlodipine, sold under the brand name Norvasc among others, is a medication used to treat high blood pressure and coronary artery disease. While calcium channel blockers are not typically recommended in heart failure, amlodipine may be used if other medications are not sufficient for high blood pressure or heart related chest pain. Amlodipine is taken by mouth and has an effect for at least a day.

Common side effects include: swelling, feeling tired, abdominal pain, and nausea. Serious side effects may include low blood pressure or a heart attack. It is unclear if use is safe during pregnancy or breastfeeding. Doses should be decreased in people with liver problems and in elderly individuals. Amlodipine is a long acting calcium channel blocker of the dihydropyridine type. It works partly by increasing the size of arteries.

Amlodipine was first patented in 1986 with commercial sale beginning in 1990. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. Wholesale cost in the developing world is 0.003 to 0.066 USD per day for a typical dose as of 2015. In the United States, a month's supply costs less than 25 USD.

Amlodipine is used in the management of hypertension and coronary artery disease in people with either stable angina (where chest pain occurs mostly after physical or emotional stress) or vasospastic angina (where it occurs in cycles) and without heart failure. It can be used as either monotherapy or combination therapy for the management of hypertension or coronary artery disease. Amlodipine can be administered to adults and children 6–17 years of age.