Felodipine

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Felodipine
(±)-Felodipine formulae V.1.svg
Felodipine-from-xtal-1989-3D-balls.png
Systematic (IUPAC) name
(RS)-3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Clinical data
Trade names Plendil
AHFS/Drugs.com monograph
MedlinePlus a692016
Pregnancy cat.
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 15% [1]
Metabolism Hepatic
Half-life ??
Excretion Renal
Identifiers
CAS number 72509-76-3 YesY
ATC code C08CA02
PubChem CID 3333
IUPHAR ligand 4190
DrugBank DB01023
ChemSpider 3216 YesY
UNII OL961R6O2C YesY
KEGG D00319 YesY
ChEBI CHEBI:585948 YesY
ChEMBL CHEMBL1480 YesY
Chemical data
Formula C18H19Cl2NO4 
Mol. mass 384.259 g/mol
 YesY (what is this?)  (verify)

Felodipine is a calcium channel blocker (calcium antagonist), a drug used to control hypertension (high blood pressure). It is marketed under the brand name Plendil by AstraZeneca and Renedil by Sanofi-Aventis. The formulation patent for the substance expired in 2007.

AstraZeneca dropped Plendil from its support and AZ&Me free Rx access program in October 2008.

Interactions[edit]

Studies dating back to 1989 have suggested that felodipine in combination with grapefruit juice can cause toxic effects. Oral administration of felodipine is first metabolized in the gastrointestinal tract and liver by the enzyme CYP3A4. Grapefruit juice contains bergamottin which is found to have an inhibiting effect over this enzyme and as a result the bioavailability of the drug increases, raising the risk for abnormal side effects.[2]

Contraindications and cautions[edit]

Contraindicated with allergy to felodipine or other calcium channel blockers, sick sinus syndrome, heart block (second and third degree), lactation. Use cautiously with pregnancy, impaired hepatic function.

Synthesis[edit]

Felodipine syn.png

Berntsson, P. B.; Carlsson, A. I.; Gaarder, J. O.; Ljung, B. R.; 1981, U.S. Patent 4,264,611.

References[edit]

  1. ^ AstraZeneca MI Department, 16th April 2010.
  2. ^ Jawad Kiani, Sardar Z Imam (October 30, 2007). "Medicinal importance of grapefruit juice and its interaction with various drugs". Nutr J. 6 (33): 33. doi:10.1186/1475-2891-6-33. PMC 2147024. PMID 17971226. Retrieved 2008-04-09. .