105618-03-9

Basic information

• Product Name: (S)-Felodipine
• Synonyms: (S)-(-)-Felodipine;(S)-Felodipine;3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (4S)-;3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (S)-;(4S)-4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester;(4S)-4β-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl ester
• CAS NO: 105618-03-9
• Molecular Formula: C₁₈H₁₉Cl₂NO₄
• Molecular Weight: 384.25
• Product Categories: Dihydropyridine Class Chemicals;Intermediates & Fine Chemicals;Pharmaceuticals;Dihydropyridine;Dihydropyridine, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 105618-03-9.mol

Chemical Properties

• Boiling Point: 471.5°Cat760mmHg
• Flash Point: 239°C
• Appearance: /
• Density: 1.277g/cm³
• Vapor Pressure: 4.62E-09mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: (S)-Felodipine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Felodipine(105618-03-9)
• EPA Substance Registry System: (S)-Felodipine(105618-03-9)

Safety Data

• Hazardous Substances Data: 105618-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Felodipine is used as a calcium channel blocker for the treatment of hypertension (high blood pressure). It helps to relax the blood vessel walls, allowing for better blood flow and a reduction in blood pressure.
Additionally, (S)-Felodipine is used as a calcium channel blocker for the management of angina pectoris, a condition characterized by chest pain due to insufficient blood supply to the heart. By relaxing the blood vessels, it improves blood flow to the heart and reduces the frequency and severity of angina attacks.
Furthermore, (S)-Felodipine is utilized as a calcium channel blocker for treating certain types of arrhythmias (irregular heartbeats). It can help regulate the heart's rhythm by controlling the electrical signals within the heart.

InChI:InChI=1/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/t15-/m0/s1

Upstream product

• 1352187-22-4 C₂₆H₂₇Cl₂NO₇S 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 1215080-66-2 (R)-3-ethyl 5-((R)-1-hydroxy-3-(phenylthio)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 1215080-64-0 (4S)-3-ethyl 5-(1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 1215080-63-9 (2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl 2-(2,3-dichlorobenzylidene)-3-oxobutanoate 
• 127634-11-1 (R)-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 
• 105580-46-9 (R)-(+)-4-(2,3-dichlorophenyl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylic acid 
• 164263-06-3 (S)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid 
• 72509-76-3 ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate 
• 64-17-5 ethanol 
• 127634-13-3 (S)-4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoethyl 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.

A facile synthesis of (S)-felodipine

A short and facile synthesis of (S)-felodipine was developed starting from (R)-glycidol as the source of the chiral auxiliary. 2-Hydroxyethyl esters were found to undergo selective transesterification reactions in the presence of other esters. This selective transesterification reaction was applied to the synthesis of (S)-felodipine through selective substitution of the 2-hydroxyethyl group possessing chiral ester with sodium methoxide.

Enantioselective retention of 4-aryl-1,4-dihydropyridine calcium-channel blockers on human serum albumin and α1-acid glycoprotein HPLC columns: Relationships with different scales of lipophilicity

The enantioselective retention of eight 4-aryl-1,4-dihydropyridine (DHP) calcium-channel blockers on HPLC stationary phases supporting human serum albumin (HSA) or α1-acid glycoprotein (AGP) was investigated. All chiral neutral DHPs were resolved on the AGP column, whereas, on the HSA column, only isradipine showed a split chromatographic peak. Analyses performed on AGP with eluents containing dimethyloctylamine (DMOA) as thc displacer demonstrated that the protein has at least two binding sites for DHPs. The first family of binding sites is enantioselective, binds exclusively to the (R)-forms, and presumably interacts competitively with DMOA. The second family of binding sites appears to be non-enantioselective and is affected by a cooperative interaction with DMOA. For the selected set of DHPs, the lipophilicity scale in octan-1-ol/H2O (log P) was not collinear with log k(w)(IAM) values obtained with immobilized artificial membranes (IAM-HPLC) due to the inclusion of both neutral and basic congeners. Only for the neutral DHPs did log k(w)(IAM) behave as a better descriptor than log P for retention date on HSA and AGP. In fact, the behavior of the basic DHPs amlodipine and nicardipine on both proteins correlated better with the octan- 1-ol/H2O log P values. We, therefore, infer that the amphipathic nature of the IAM phase only mimics the interaction of non-ionizable compounds with serum proteins. In contrast, the IAM-HPLC retention data of protonated bases encode additional interaction mechanisms that are specific for phospholipids and not involved in ligand-protein interactions.

Determination of the absolute configuration of biologically active (S)-(-)-NB 818 and its structural correlation with the stereoselectivity of the channel blocking action

The absolute configuration of 4-(2,3-dichlorophenyl)-1,4-dihydropyridines was established by chemical correlation with (S)-(-)-felodipine, the absolute configuration of which had been determined by X-ray analysis.

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