1217757-71-5

Basic information

• Product Name: (R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL
• Synonyms: (R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL;(R)-(+)-M4;(R)-(+)-BM 140830;(R)-3-[2-[[3-(9H-Carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]-4-methoxyphenol;(R)-5-Hydroxycarvedilol;3-[2-[[(2R)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]-4-methoxyphenol
• CAS NO: 1217757-71-5
• Molecular Formula: C24H26N2O5
• Molecular Weight: 422.47
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 1217757-71-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 205-207°C
• Boiling Point: 702.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.305±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• PKA: 10.06±0.18(Predicted)
• CAS DataBase Reference: (R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL(1217757-71-5)
• EPA Substance Registry System: (R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL(1217757-71-5)

Safety Data

• Hazardous Substances Data: 1217757-71-5(Hazardous Substances Data)

Usage

Description

(R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL is an optically active metabolite of Carvedilol, a multiple-action, neurohormonal antagonist used in the treatment of hypertension. It is characterized by its off-white powder form and possesses unique chemical properties due to its optical activity.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL is used as a pharmaceutical compound for the treatment of hypertension. As an optically active metabolite of Carvedilol, it contributes to the drug's efficacy in managing blood pressure levels.
Used in Cardiovascular Applications:
(R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL is used as a nonselective β-adrenergic blocker with α1-blocking activity. This dual action allows it to be effective in treating various cardiovascular conditions, such as hypertension, by modulating the sympathetic nervous system and reducing the workload on the heart.
Used in Drug Development:
(R)-(+)-5'-HYDROXYPHENYL-CARVEDILOL is used as a key component in the development of new drugs targeting cardiovascular diseases. Its unique properties and activity as a metabolite of Carvedilol make it a valuable candidate for research and development in the pharmaceutical industry.

Upstream product

• 219685-46-8 3-(2-bromoethoxy)-4-methoxy benzaldehyde 
• 621-59-0 isovanillin 
• 1262778-72-2 3-(2-bromoethoxy)-4-methoxyphenol 
• 1262778-73-3 4-methoxy-3-(2-phthalimidoethoxy)phenol 
• 1262778-75-5 3-(2-aminoethoxy)-4-methoxyphenol hydrochloride 
• 51997-51-4 4-(2,3-epoxypropoxy)carbazole 
• 1262778-71-1 formic acid 3-(2-bromoethoxy)-4-methoxyphenyl ester 
• 52602-39-8 9H-carbazol-4-ol 
• 1076198-81-6 C₉H₁₃NO₃ 

Relevant articles and documents

Suppression of store overload-induced calcium release by hydroxylated metabolites of carvedilol

Carvedilol is a drug widely used in the treatment of heart failure and associated cardiac arrhythmias. A unique action of carvedilol is its suppression of store overload-induced calcium release (SOICR) through the cardiac ryanodine receptor (RyR2), which can trigger ventricular arrhythmias. Since the effects of carvedilol metabolites on SOICR have not yet been investigated, three carvedilol metabolites hydroxylated at the 3-, 4′ and 5′-positions were synthesized and assayed for SOICR inhibition in mutant HEK 293 cells expressing the RyR2 mutant R4496C. This cell line is especially prone to SOICR and calcium release through the defective RyR2 channel was measured with a calcium-sensitive fluorescent dye. These results revealed that the 3- and 4′-hydroxy derivatives are slightly more effective than carvedilol in suppressing SOICR, while the 5′-analog proved slightly less active. Metabolic deactivation of carvedilol via these hydroxylation pathways is therefore insignificant.