99200-09-6

Basic information

• Product Name: Nebivolol
• Synonyms: NEBIVOLOL-D4;1-(6-fluorochroman-2-yl)-2-[[2-(6-fluorochroman-2-yl)-2-hydroxy-ethyl]amino]ethanol;Nibivolol;R-65824;α,α'-(Iminobismethylene)bis(6-fluoro-2-chromanmethanol);Nebivolol;1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-[[2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl]amino]ethanol;1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-[[2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxy-ethyl]amino]ethanol
• CAS NO: 99200-09-6
• Molecular Formula: C₂₂H₂₅F₂NO₄
• Molecular Weight: 405.43
• Product Categories: Antihypertensive
• Mol File: 99200-09-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 600.455 °C at 760 mmHg
• Flash Point: 316.944 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 2.88E-15mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.29±0.20(Predicted)
• CAS DataBase Reference: Nebivolol(CAS DataBase Reference)
• NIST Chemistry Reference: Nebivolol(99200-09-6)
• EPA Substance Registry System: Nebivolol(99200-09-6)

Safety Data

• Hazardous Substances Data: 99200-09-6(Hazardous Substances Data)

Usage

Description

Nebivolol, marketed under the brand name Nebilet, is a selective β1-adrenergic receptor antagonist with vasodilating properties via the nitric oxide pathway. It is used as an antihypertensive agent and is prepared through a five-step synthesis process starting with 6-fluoro-4-oxobenzopyran-2-carboxylic acid. Nebivolol is a member of the chromanes class, specifically 2,2'-iminodiethanol, with a 6-fluorochroman-2-yl group replacing one hydrogen attached to each hydroxy-bearing carbon.

Uses

Used in Pharmaceutical Industry:
Nebivolol is used as an antihypertensive agent for the treatment of hypertension. It selectively targets β1-adrenergic receptors, making it 50 times less potent at β2-receptors, and helps in reducing blood pressure. The immediate fall in blood pressure upon administration, along with improvements in left ventricular systolic and diastolic function and lowering of peripheral blood resistance, make it an effective treatment option.
Additionally, Nebivolol is used as an internal standard for the quantification of Nebivolol by GCor LC-mass spectrometry, ensuring accurate measurements and analysis in pharmaceutical research and development.
Compared to atenolol, Nebilet (Nebivolol) does not influence insulin sensitivity or lipid profiles, making it a safer choice for patients with concerns related to these factors. While 50 mg of atenolol and 10 mg of Nebilet are equipotent, Nebilet has a longer duration of action due to the accumulation of the drug and increasing plasma levels of active metabolites.

InChI:InChI=1/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2

Upstream product

• 682359-63-3 N-[(S,S)-1-hydroxy-2-(6-fluoro-chroman-4-one-2-yl)]-N-[(R,S)-1-hydroxy-2-(6-fiuoro-chroman-4-one-2-yl)]-amine 
• 797054-41-2 N-benzyl-N-[(R,R)-1-hydroxy-2-(6-fluoro-chroman-4-one-2-yl)]-N-[(S,R)-1-hydroxy-2-(6-fluoro-chroman-4-one-2-yl)]-amine 
• 129050-27-7 (S*,R*)-(±)-α-[(benzylamino)methyl](6-fluoro-2-chromanyl)methanol 
• 103-49-1 dibenzylamine 
• 100-46-9 benzylamine 
• 99199-90-3 6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran 
• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 409346-73-2 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde 
• 129050-27-7 (R*,R*)-(±)-α-[(benzylamino)methyl](6-fluoro-2-chromanyl)methanol 
• 99199-60-7 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid 
• 99199-62-9 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol 
• 929706-85-4 α,α'-[[(phenylmethyl)imino]bismethylene]bis-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] 
• 99199-59-4 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid 
• 99199-91-4 6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol 

Downstream Products

• 118457-14-0 (+)-Nebivolol 
• 118457-16-2 nebivolol 
• 152520-56-4 DL-nebivolol hydrochloride 
• 169293-50-9 nebivolol hydrochloride 
• 9920-09-6 α,α'-iminobis(methylene)bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride 
• 920299-33-8 (R)-1-((R)-6-Fluoro-chroman-2-yl)-2-[(S)-2-((R)-6-fluoro-chroman-2-yl)-2-hydroxy-ethylamino]-ethanol; hydrochloride 
• 152520-56-4 nebivolol hydrochloride 

Relevant articles and documents

Preparation method and application of Smo inhibitor based on Nebivolol

The invention discloses a preparation method and an application of a Smo inhibitor based on Nebivolol. The structural formula of the Smo inhibitor is as shown in a formula (I). The invention further discloses a synthetic method and an application of the Smo inhibitor. According to the Smo inhibitor, a beta-receptor retardant Nebivolol with inhibitory activity for Smo proteins serves as a lead compound, and optimization reconstruction is implemented based on the beta-receptor retardant Nebivolol to obtain the Smo inhibitor with good inhibitory activity.

PREPARATION OF NEBIVOLOL

Processes for the synthesis of pharmacologically active 2,2-iminobisethanol derivatives, e.g., 2H-1-benzopyran-2 methanol-α,α′-iminobis(methylene)]bis-[6-fluoro-3,4-dihydro-[2R*[R*[R*(S*)]]]], and their pharmaceutically acceptable salts.

PROCESS FOR PREPARING NEBIVOLOL

The present invention relates to a process for preparing Nebivolol and, more particularly, to an improved method of debenzylation of a compound of formula (II) useful for preparing nebivolol endowed with high purity.