119945-59-4

Basic information

• Product Name: (R)-Felodipine
• Synonyms: (R)-Felodipine;3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (4R)-;3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (R)-;(4R)-4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester;(4R)-4α-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl ester
• CAS NO: 119945-59-4
• Molecular Formula: C₁₈H₁₉Cl₂NO₄
• Molecular Weight: 384.25
• Product Categories: Dihydropyridine Class Chemicals;Intermediates & Fine Chemicals;Pharmaceuticals;Dihydropyridine;Dihydropyridine, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 119945-59-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (R)-Felodipine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Felodipine(119945-59-4)
• EPA Substance Registry System: (R)-Felodipine(119945-59-4)

Safety Data

• Hazardous Substances Data: 119945-59-4(Hazardous Substances Data)

Usage

Description

(R)-Felodipine, the enantiomer R of Felodipine, is a dihydropyridine calcium channel blocker. It is a pharmaceutical compound that selectively blocks the movement of calcium ions across cell membranes, particularly in the heart and blood vessels. This action results in the relaxation of blood vessel walls, leading to a decrease in blood pressure and improved blood flow.

Uses

Used in Pharmaceutical Industry:
(R)-Felodipine is used as a dihydropyridine calcium channel blocker for the treatment of hypertension (high blood pressure) and angina pectoris (chest pain due to insufficient blood supply to the heart). By blocking calcium channels, it helps to relax the smooth muscles in the walls of blood vessels, leading to vasodilation and a reduction in peripheral vascular resistance. This, in turn, lowers blood pressure and alleviates the symptoms of angina.
Additionally, (R)-Felodipine may be used in other applications within the pharmaceutical industry, such as for the treatment of other cardiovascular conditions or as a component in drug delivery systems to enhance the efficacy and targeted delivery of other medications.

Upstream product

• 127634-14-4 (R)-4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoethyl ester 
• 74-88-4 methyl iodide 
• 72509-76-3 ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate 
• 127634-12-2 (S)-4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-[(R)-1-hydroxymethyl-2-(toluene-4-sulfonyl)-ethyl] ester 

Relevant articles and documents

Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography

Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak IC (250?×?4.6?mm i.d., 5?μm) column. Then the influence of the mobile phase including an alcohol-modifying agent and alkaline additive on the enantioseparation were investigated and optimized. The optimal mobile phase conditions and maximum resolution for every analyte were as follows respectively: n-hexane/isopropanol (85:15, v/v) for nimodipine (R?=?5.80) and cinildilpine (R?=?5.65); n-hexane/isopropanol (92:8, v/v) for nicardipine (R?=?1.76) and nisoldipine (R?=?1.92); and n-hexane/isopropanol/ethanol (97:2:1, v/v/v) for felodipine (R?=?1.84) and lercanidipine (R?=?1.47). Relative separation mechanisms are discussed based on the separation results, and indicate that the achiral parts in the analytes' structure showed an important influence on the separation of the chiral column.

SYNTHESIS OF THE ENANTIOMERS OF FELODIPINE AND DETERMINATION OF THEIR ABSOLUTE CONFIGURATION

The pure enantiomers of felodipine, 1, have been synthesized by chromatographic separation of diastereomeric esters with (R)-1-(p-toluenesulfonyl)-3-trityloxypropan-2-ol, 3, as an easily removable chiral auxiliary.Absolute configurations have been deduced