Felodipine

HCID 178793668CAS 1346602-65-0

Grundinformationen

Standard-SMILES
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl
InChIKey
RZTAMFZIAATZDJ-UHFFFAOYSA-N
Summenformel
C18H19Cl2NO4
Durchschnittliche Molmasse
384,2 g/mol

Überblick

Felodipine is the mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris. It has a role as a vasodilator agent, an antihypertensive agent, an anti-arrhythmia drug and a calcium channel blocker. It is a dichlorobenzene, an ethyl ester, a methyl ester and a dihydropyridine.

Namen und Bezeichner

Bevorzugter Name
Felodipine
IUPAC
5-O-ethyl 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Englischer Name
RZTAMFZIAATZDJ-GCWKZCQISA-N
Summenformel
C18H19Cl2NO4
Molmasse
384.25

Namen und Synonyme

felodipine72509-76-3PlendilFlodilModipFelodipinaPreslowFelodipinumDTXSID4023042H 154/82Felodipino4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester
Weitere Namen anzeigen
RZTAMFZIAATZDJ-GCWKZCQISA-N
NSC-760343OL961R6O2CC08CA02(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylateDTXCID3030423,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl esterCHEBI:585948

Datenbank-Bezeichner

CAS
1346602-65-0
ChEMBL
CHEMBL1480、CHEMBL3196476
ChEBI
CHEBI:585948
UNII
OL961R6O2C
EC Number
620-472-7
Nikkaji
J11.263A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,9
Polarare Oberfläche (TPSA)
64,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
6
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals
LogP · 2 Einträge

3.8

3.65

Solubility7.15e-03 g/L
Human Drugs · 4 Einträge

Breast Feeding; Lactation; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point145 °C
Physical DescriptionSolid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (93.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 59 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (93.2%)

Toxikologische Informationen

Adverse EffectsThe adverse effects of felodipine are classified as either dose-dependent or dose-independent.
Toxicity Summary · 1 Eintrag

A mild-to-moderate overdose of felodipine can result in hypotension secondary to peripheral vasodilation and reflex tachycardia. However, a severe overdose of felodipine can cause life-threatening profound hypotension and bradycardia. Case fatality due to profound, refractory circulatory collapse overdose has been reported in the literature. The risk of overdose increases in elderly individuals, patients with liver impairment, and concomitant administration of felodipine with beta blockers. Overdose symptoms can include lightheadedness, syncope, altered mental status, and shock secondary to profound hypotension. The insulin release from the pancreas depends on calcium influx through the L-type channels. Felodipine blocks these calcium channels and results in hyperglycemia because of decreased insulin release.

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Felodipine

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

C08CA02

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding99%, primarily to the albumin fraction.
Pharmacodynamics · 1 Eintrag

Felodipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. It was widely accepted that CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction; however, some studies have shown that felodipine also binds to and inhibits T-type calcium channels. T-type calcium channels are most commonly found on neurons, cells with pacemaker activity and on osteocytes. The pharmacologic significance of T-type calcium channel blockade is unknown. Felodipine also binds to calmodulin and inhibits calmodulin-dependent calcium release from the sarcoplasmic reticulum. The effect of this interaction appears to be minor. Another study demonstrated that felodipine attenuates the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase (CaMPDE) by binding to the PDE-1B1 and PDE-1A2 enzyme subunits. CaMPDE is one of the key enzymes involved in cyclic nucleotides and calcium second messenger systems. Felodipine also acts as an antagonist to the mineralcorticoid receptor by competing with aldosterone for binding and blocking aldosterone-induced coactivator recruitment of the mineralcorticoid receptor. Felodipine is able to bind to skeletal and cardiac muscle isoforms of troponin C, one of the key regulatory proteins in muscle contraction. Though felodipine exhibits binding to many endogenous molecules, its vasodilatory effects are still thought to be brought about primarily through inhibition of voltage-gated L-type calcium channels. Similar to other DHP CCBs, felodipine binds directly to inactive calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives felodipine additional arterial selectivity. At therapeutic sub-toxic concentrations, felodipine has little effect on cardiac myocytes and conduction cells.

Mechanism of Action · 1 Eintrag

Felodipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through voltage-gated L-type calcium channels. It reversibly competes against nitrendipine and other DHP CCBs for DHP binding sites in vascular smooth muscle and cultured rabbit atrial cells. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium decreases the contractile activity of arterial smooth muscle cells and results in vasodilation. The vasodilatory effects of felodipine result in an overall decrease in blood pressure. Felodipine may be used to treat mild to moderate essential hypertension.

Biological Half-Life17.5-31.5 hours in hypertensive patients; 19.1-35.9 hours in elderly hypertensive patients; 8.5-19.7 in healthy volunteers.
Metabolism/MetabolitesHepatic metabolism primarily via cytochrome P450 3A4. Six metabolites with no appreciable vasodilatory effects have been identified.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationPharmaceuticals

Anwendungen

VerwendenA labelled dihydropyridine calcium channel blocker.

Anbieter2 Anbieter

安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
南京世洲生物科技有限公司17301488900 · [email protected]

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