Levonebivolol

Base Information

• Chemical Name: Levonebivolol
• CAS No.: 118457-16-2
• Molecular Formula: C22H25 F2 N O4
• Molecular Weight: 405.442
• European Community (EC) Number: 601-527-4
• UNII: GMK2E335DQ
• Nikkaji Number: J330.677A
• Wikidata: Q27132969
• NCI Thesaurus Code: C91033
• Metabolomics Workbench ID: 63091
• ChEMBL ID: CHEMBL2365658
• Mol file: 118457-16-2.mol

Synonyms:Levonebivolol;118457-16-2;l-nebivolol;(-)-Nebivolol;Levonebivolol [INN];UNII-GMK2E335DQ;118457-14-0;(-)-SSSR-nebivolol;(R,S,S,S)-nebivolol;R 67145;GMK2E335DQ;Bystolic;CHEBI:64020;Vasoxen;Nebivolol Impurity A;(1S,1'S)-2,2'-iminobis{1-[(2R,2'S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]ethanol};(S)-1-((R)-6-fluorochroman-2-yl)-2-(((S)-2-((S)-6-fluorochroman-2-yl)-2-hydroxyethyl)amino)ethan-1-ol;[2R,alphaS,2'S,alpha'S]-alpha,alpha'-[imino-bis(methylene)]bis[6-fluoro-3,4-dehydro-2H-1-benzopyran-2-methanol];Nebivolol (USAN/INN);R-67145;rel-Nebivolol;(1S)-1-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-[[(2S)-2-[(2R)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]amino]ethanol;l-Nebivolol;alpha,alpha'-(iminodi-methylene)bis[6-fluoro-2-chromanmethanol];LEVONEBIVOLOL [WHO-DD];SCHEMBL7919700;CHEMBL2365658;KOHIRBRYDXPAMZ-YHDSQAASSA-N;HMS3886O20;(alpha R,-alpha'R,2R,2'S)-rel-alpha,-alpha'-[Iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol];HY-B0203;s5739;AKOS040752538;AT27091;CS-O-31133;D05127;R67145;Q27132969;(+/-)[R*,S*,S*,S*]-alpha,alpha'-[imino-bis (methylene)] bis [6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol];(|AS,|A inverted exclamation markaS,2R,2 inverted exclamation markaS)-|A,|A inverted exclamation marka-[Iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol];(1S)-2-(((2S)-2-((2R)-6-FLUORO-3,4-DIHYDRO-2H-CHROMEN-2-YL)-2-HYDROXYETHYL)AMINO)-1-((2S)-6-FLUORO-3,4-DIHYDRO-2H-CHROMEN-2-YL)ETHANOL;2H-1-Benzopyran-2-methanol, alpha,alpha'-(iminobis(methylene))bis(6-fluoro-3,4-dihydro-, (2S-(2R*(R*(R*(S*)))))-

Chemical Property of Levonebivolol

Chemical Property:

• Vapor Pressure: 2.88E-15mmHg at 25°C
• Melting Point: 135-137°C
• Boiling Point: 600.5°Cat760mmHg
• PKA: 14.29±0.20(Predicted)
• Flash Point: 316.9°C
• PSA: 70.95000
• Density: 1.309g/cm³
• LogP: 2.75450
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 405.17516460
• Heavy Atom Count: 29
• Complexity: 483

Purity/Quality:

98%Min ^*data from raw suppliers

(-)-Nebivolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC(=C2)F)OC1C(CNCC(C3CCC4=C(O3)C=CC(=C4)F)O)O
• Isomeric SMILES: C1CC2=C(C=CC(=C2)F)O[C@H]1[C@H](CNC[C@@H]([C@@H]3CCC4=C(O3)C=CC(=C4)F)O)O
• Recent EU Clinical Trials: Effects of nebivolol on the cardiovascular functions, thermoregulation and blood flow during real and simulated conditions of microgravity
• Uses: (-)-Nebivolol is a β1-Adrenergic blocker. Used as an antihypertensive.

Technology Process of Levonebivolol

There total 13 articles about Levonebivolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

→ nebivolol (118457-16-2,118457-14-0,118457-15-1,119365-25-2,119365-23-0,1360598-84-0)

Guidance literature:

Reference yield: 67.0%

l-(R,S,S,S)-benzyl nebivolol hydrochloride (1224567-85-4) → nebivolol (118457-16-2,118457-14-0,118457-15-1,119365-25-2,119365-23-0,1360598-84-0)

Guidance literature:

l-(R,S,S,S)-benzyl nebivolol hydrochloride; With sodium hydroxide; In water; iso-butanol; at 25 ℃; Inert atmosphere;

With formic acid; 5% Pd(II)/C(eggshell); In iso-butanol; at 70 ℃; for 4h;

With sodium hydroxide; In water; iso-butanol;

Reference yield: 62.0%

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 (682359-63-3) → nebivolol (118457-16-2,118457-14-0,118457-15-1,119365-25-2,119365-23-0,1360598-84-0)

Guidance literature:

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; With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In ethanol; water; at 50 - 55 ℃; for 16h; under 2250.23 Torr;

With sodium hydrogencarbonate; In water; pH=8;

upstream raw materials:

nebivolol

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

(2S)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene

2-amino-1-[6-fluoro-(2R)-3H,4H-2-chromenyl]-(1S)-ethan-1-ol

Downstream raw materials:

nebivolol hydrochloride

Refernces

• 1、 -. "A process for the preparation of nebivolol and wherein the intermediate compound". Paragraph 0088; 0089. . Retrieved 2016/11/17.
• 2、 -. "PREPARATION OF NEBIVOLOL". . . Retrieved 2011/10/19.