95094-00-1

Basic information

• Product Name: (S)-(-)-CARVEDILOL
• Synonyms: (-)-1-(9H-CARBAZOL-4-YLOXY)-3-[[2-(2-METHOXYPHENOXY)ETHYL]AMINO]-2-PROPANOL;(S)-(-)-CARVEDILOL;2-Propanol, 1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-, (2S)-;2-Propanol, 1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-, (S)-;(2S)-1-(9H-Carbazole-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]propane-2-ol;(S)-1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol;[S,(-)]-1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol;Carvedilol S-IsoMer
• CAS NO: 95094-00-1
• Molecular Formula: C₂₄H₂₆N₂O₄
• Molecular Weight: 406.47
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles;API
• Mol File: 95094-00-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 114-115°C
• Boiling Point: 655.2 °C at 760 mmHg
• Flash Point: 350.1 °C
• Appearance: Colourless crystalline solid
• Density: 1.25 g/cm³
• Vapor Pressure: 4.63E-18mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: -20°C Freezer
• PKA: 13.90±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-CARVEDILOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-CARVEDILOL(95094-00-1)
• EPA Substance Registry System: (S)-(-)-CARVEDILOL(95094-00-1)

Safety Data

• Hazardous Substances Data: 95094-00-1(Hazardous Substances Data)

Usage

Uses

(S)-(-)-CARVEDILOL is the optically active isomer of Carvedilol, a nonselective -adrenergic blocker with a1-blocking activity. It is an antihypertensive used in the treatment of congestive heart failure.

InChI:InChI=1/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3/t17-/m1/s1

Upstream product

• 293738-17-7 N-[2-(2-methoxyphenoxy)ethyl]acetamide 
• 90-05-1 2-methoxy-phenol 
• 591-20-8 3-Bromophenol 
• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 
• 95093-95-1 S-(+)-4-(oxiranylmethoxy)-9H-carbazole 
• 52602-39-8 9H-carbazol-4-ol 
• 72956-09-3 carvedilol 
• 180988-02-7 C₂₅H₂₄N₂O₅ 
• 95093-96-2 (R)-4-(oxiran-2-ylmethoxy)-9H-carbazole 
• 180988-03-8 C₂₅H₂₄N₂O₅ 

Relevant articles and documents

In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation

In this work, the phase-transitioned BSA (PTB) film using the mild and fast fabrication process adhered to the capillary inner wall uniformly, and the fabricated PTB film-coated capillary column was applied to realize open tubular capillary electrochromatography (OT-CEC) enantioseparation. The enantioseparation ability of PTB film-coated capillary was evaluated with eight pairs of chiral analytes including drugs and neurotransmitters, all achieving good resolution and symmetrical peak shape. For three consecutive runs, the relative standard deviations (RSD) of migration time for intra-day, inter-day, and column-to-column repeatability were in the range of 0.3%–3.5%, 0.2%–4.9% and 2.1%–7.7%, respectively. Moreover, the PTB film-coated capillary column ran continuously over 300 times with high separation efficiency. Therefore, the coating method based on BSA self-assembly supramolecular film can be extended to the preparation of other proteinaceous capillary columns.

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

Preparation of a β-cyclodextrin-based open-tubular capillary electrochromatography column and application for enantioseparations of ten basic drugs

An open-tubular capillary electrochromatography column was prepared by chemically immobilized β-cyclodextrin modified gold nanoparticles onto new surface with the pre-derivatization of (3-mercaptopropyl)-trimethoxysilane. The synthesized nanoparticles and the prepared column were characterized by transmission electron microscopy, scanning electron microscopy, infrared spectroscopy and ultraviolet visible spectroscopy. When the column was employed as the chiral stationary phase, no enantioselectivity was observed for ten model basic drugs. So β-cyclodextrin was added to the background electrolyte as chiral additive to expect a possible synergistic effect occurring and resulting in a better separation. Fortunately, significant improvement in enantioselectivity was obtained for ten pairs of drug enantiomers. Then, the effects of β-cyclodextrin concentration and background electrolyte pH on the chiral separation were investigated. With the developed separation mode, all the enantiomers (except for venlafaxine) were baseline separated in resolutions of 4.49, 1.68, 1.88, 1.57, 2.52, 2.33, 3.24, 1.63 and 3.90 for zopiclone, chlorphenamine maleate, brompheniramine maleate, dioxopromethazine hydrochloride, carvedilol, homatropine hydrobromide, homatropine methylbromide, venlafaxine, sibutramine hydrochloride and terbutaline sulfate, respectively. Further, the possible separation mechanism involved was discussed.