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Details

Stereochemistry RACEMIC
Molecular Formula C18H19Cl2NO4
Molecular Weight 384.254
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELODIPINE

SMILES

CCOC(=O)C1=C(C)NC(C)=C(C1C2=CC=CC(Cl)=C2Cl)C(=O)OC

InChI

InChIKey=RZTAMFZIAATZDJ-UHFFFAOYSA-N
InChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C18H19Cl2NO4
Molecular Weight 384.254
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, felodipine prevents calcium-dependent myocyte contraction and vasoconstriction. Felodipine is the most potent CCB in use and is unique in that it exhibits fluorescent activity. In addition to binding to L-type calcium channels, felodipine binds to a number of calcium-binding proteins, exhibits competitive antagonism of the mineralcorticoid receptor, inhibits the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase, and blocks calcium influx through voltage-gated T-type calcium channels. Felodipine is used to treat mild to moderate essential hypertension.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Hemodynamic effects of felodipine at rest and during exercise in exertional angina pectoris.
1983 Sep 1
Haemodynamic effects of single-dose felodipine in normal man.
1985
Effects of felodipine on resistance and capacitance vessels in patients with essential hypertension.
1985
Comparative trial of felodipine and nifedipine in refractory hypertension.
1985
Antihypertensive effect of felodipine combined with beta-blockade. A comparison between 2 and 3 daily dosages.
1985
Renal and antihypertensive effects of felodipine in hypertensive patients.
1985 Dec
Renal and cardiovascular effects of acute and chronic administration of felodipine to SHR.
1985 Jul 11
Felodipine compared to nifedipine as "third-line drug" in resistant hypertension.
1986 Nov
Baroreflex control of renin release in spontaneously hypertensive rats after administration of felodipine.
1987
Felodipine, a new calcium antagonist, as monotherapy in mild or moderate hypertension. Cooperative study group.
1987
Monotherapy with felodipine, a new calcium antagonist, in mild and moderate hypertension.
1987
Catecholamines, renin-angiotensin-aldosterone, and cardiovascular response during exercise following acute and long-term calcium antagonism with felodipine in essential hypertension.
1987 Oct
A double-blind comparison of felodipine and hydrochlorothiazide added to metoprolol to control hypertension.
1988
Antihypertensive effect of felodipine or hydralazine when added to beta-blocker therapy.
1988 Jul
Felodipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension.
1988 Oct
The efficacy and tolerability of long-term felodipine treatment in hypertension. The Scandinavian Multicenter Group.
1990 Jun
Felodipine ER formulation in the treatment of mild hypertension: efficacy and tolerability vs placebo.
1990 Oct
The influence of infusion rate on the hemodynamic effects of felodipine.
1990 Sep
Felodipine in combination with a beta-adrenoceptor blocker as an effective substitute for triple therapy in severe hypertension. The Australian Felodipine Multicentre Study Group.
1991
Felodipine clinical pharmacokinetics.
1991 Dec
Acute effects on exercise tolerance of felodipine and diltiazem, alone and in combination, in stable effort angina.
1991 Jan
Extended release felodipine in essential hypertension. Variations in blood pressure during whole-day continuous ambulatory recording.
1991 Jan
Beta-adrenergic receptors and reflex tachycardia after single and repeated felodipine administration in essential hypertension.
1991 Jun
Felodipine: a new dihydropyridine calcium-channel antagonist.
1991 Nov
Long-term effects of felodipine in patients with reduced renal function.
1992 May
A multicenter comparison of isradipine and felodipine in the treatment of mild-to-moderate hypertension. The Physician's Study Group.
1993 Mar
Comparison of effects of felodipine versus hydrochlorothiazide on arterial diameter and pulse-wave velocity in essential hypertension.
1993 Oct 1
Efficacy and tolerability of extended-release felodipine and extended-release nifedipine in patients with mild-to-moderate essential hypertension.
1994 Jul-Aug
Mono- and combination therapy with felodipine or enalapril in elderly patients with systolic hypertension.
1994 Mar
Isradipine. An update of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in the treatment of mild to moderate hypertension.
1995 Apr
Global efficacy and tolerability of losartan, an angiotensin II subtype 1-receptor antagonist, in the treatment of hypertension.
1996
Losartan potassium: a review of its pharmacology, clinical efficacy and tolerability in the management of hypertension.
1996 May
Felodipine in the treatment of severe refractory hypertension.
1996 Sep
Effect of the calcium antagonist felodipine as supplementary vasodilator therapy in patients with chronic heart failure treated with enalapril: V-HeFT III. Vasodilator-Heart Failure Trial (V-HeFT) Study Group.
1997 Aug 5
Calcium antagonists, a useful additional therapy in treatment resistant hypertension: comparison of felodipine ER and nifedipine Retard by 24-h ambulatory blood pressure monitoring.
1997 Jan
Cardiovascular effects of a low-dose combination of ramipril and felodipine in spontaneously hypertensive rats.
1997 Jun
A comparison of nisoldipine coat-core and felodipine in the treatment of mild-to-moderate hypertension.
1998 Jun
Improved tolerability of felodipine compared with amlodipine in elderly hypertensives: a randomised, double-blind study in 535 patients, focusing on vasodilatory adverse events. The International Study Group.
1998 Sep
Examination of 209 drugs for inhibition of cytochrome P450 2C8.
2005 Jan
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study.
2007 Apr 17
Structure-activity relationship of 1,4-dihydropyridines as potentiators of the cystic fibrosis transmembrane conductance regulator chloride channel.
2007 Jul
Lercanidipine in the treatment of hypertension.
2007 Mar
Molecular mechanisms of felodipine suppressing atherosclerosis in high-cholesterol-diet apolipoprotein E-knockout mice.
2008 Feb
Felodipine reduces cardiac expression of IL-18 and perivascular fibrosis in fructose-fed rats.
2008 Jul-Aug
Chloride channels as drug targets.
2009 Feb
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010 Feb 23
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Evaluation of in vitro cytochrome P450 induction and inhibition activity of deoxyelephantopin, a sesquiterpene lactone from Elephantopus scaber L.
2013 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hypertension Initial dose: 5 mg orally once a day Maintenance dose: 2.5 to 10 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
the maximum contraction to NA in rat vessels exposed to felodipine (0.1 umol/L) was reduced by 37%, and the contraction to K+ (62 mmol/L) was reduced by 84% compared with vehicle-treated arteries.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:24:57 UTC 2019
Edited
by admin
on Tue Oct 22 00:24:57 UTC 2019
Record UNII
OL961R6O2C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FELODIPINE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
PLENDIL
Brand Name English
FELODIPINE [USP-RS]
Common Name English
FELODIPINE [MART.]
Common Name English
FELODIPINE [EP]
Common Name English
FELODIPINE [VANDF]
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-, ETHYL METHYL ESTER, (+/-)-
Common Name English
FELODIPINE [WHO-DD]
Common Name English
FELODIPINE [ORANGE BOOK]
Common Name English
FELODIPINE [USAN]
Common Name English
FELODIPINE [MI]
Common Name English
LEXXEL COMPONENT FELODIPINE
Common Name English
FELODIPINE COMPONENT OF LEXXEL
Common Name English
H-154/82
Code English
C08CA02
Code English
H 154/82
Code English
FELODIPINE [INN]
Common Name English
(+/-)-ETHYL METHYL 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE
Systematic Name English
FELODIPINE [JAN]
Common Name English
FELODIPINE [USP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
WHO-ATC C08CA02
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
WHO-VATC QC09BB05
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
WHO-VATC QC08CA02
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
NDF-RT N0000007556
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
LIVERTOX 402
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
NDF-RT N0000175421
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
NDF-RT N0000000069
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
WHO-ATC C09BB05
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
Code System Code Type Description
CAS
72509-76-3
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
MERCK INDEX
M5257
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
FELODIPINE
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
DRUG BANK
DB01023
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
RXCUI
4316
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY RxNorm
MESH
D015736
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
PUBCHEM
3333
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
EPA CompTox
72509-76-3
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
EVMPD
SUB11963MIG
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
LactMed
72509-76-3
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
INN
4877
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
IUPHAR
4190
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
ChEMBL
CHEMBL1480
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
NCI_THESAURUS
C29046
Created by admin on Tue Oct 22 00:24:57 UTC 2019 , Edited by admin on Tue Oct 22 00:24:57 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC