Bevantolol hydrochloride

Base Information

• Chemical Name: Bevantolol hydrochloride
• CAS No.: 42864-78-8
• Molecular Formula: C20H27NO4^.HCl
• Molecular Weight: 381.9
• Hs Code.: 2922299090
• European Community (EC) Number: 834-176-2
• UNII: 4VB9HU07BC
• DSSTox Substance ID: DTXSID5048633
• Wikidata: Q27114262
• NCI Thesaurus Code: C142952
• ChEMBL ID: CHEMBL2106060
• Mol file: 42864-78-8.mol

Synonyms:bevantolol;bevantolol hydrochloride;CI 775;CI-775

Chemical Property of Bevantolol hydrochloride

Chemical Property:

• Vapor Pressure: 1.44E-11mmHg at 25°C
• Melting Point: 137-138°
• Boiling Point: 518.3 °C at 760 mmHg
• Flash Point: 267.3 °C
• PSA: 59.95000
• LogP: 3.77710
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 381.1706861
• Heavy Atom Count: 26
• Complexity: 355

Purity/Quality:

99% ^*data from raw suppliers

Bevantolol Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)OCC(CNCCC2=CC(=C(C=C2)OC)OC)O.Cl
• Recent ClinicalTrials: Efficacy and Safety on SOM3355 in Huntington's Disease Chorea
• Recent EU Clinical Trials: Phase IIb, randomized, double-blind, placebo-controlled study in parallel groups assessing the efficacy and safety of two doses of SOM3355 in patients suffering from Huntington’s Disease with choreic movements.
• Description: Bevantolol hydrochloride is a cardioselective (β1) adrenergic blocker, devoid of intrinsic sympathomimetic and local anesthetic activities. As with other agents of this category, it is useful in the treatment of hypertension and angina. Bevantolol is an antagonist of the β1-adrenergic receptor (β1-AR; Ki = 14.79 nM in rat cortical membranes). It is selective for β1- over β2-ARs (Ki = 588.84 nM), as well as α2-ARs up to 100 μM, but is an antagonist of α1-ARs (Ki = 125.89 nM). Bevantolol inhibits low voltage-activated calcium currents (LVA-ICa) in dissociated rat ventro-medial hypothalamic neurons (IC50 = 40 μM). It inhibits norepinephrine-induced contraction of isolated rabbit thoracic aorta (pA2 = 4.77), isoprenaline-induced inotropic effects in isolated guinea pig right atria (pA2 = 7.74), and isoprenaline-induced relaxation of isolated guinea pig trachea (pA2 = 6.69). Bevantolol (250 mg/kg per day) prevents immobilization stress-induced increases in systolic blood pressure in a rat model of stress-induced hypertension.
• Uses: Bevantolol is a cardioselective β-adrenergic blocker. Bevantolol is used as an antianginal, antihypertensive, antiarrhythmic.

Technology Process of Bevantolol hydrochloride

There total 3 articles about Bevantolol hydrochloride 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: 75.8%

→ bevantolol hydrochloride (42864-78-8)

Guidance literature:

Reference yield: 54.0%

m-tolyl glycidyl ether (2186-25-6) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → bevantolol hydrochloride (42864-78-8)

Guidance literature:

m-tolyl glycidyl ether; 2-(3,4-dimethoxyphenyl)-ethylamine; In ethanol; at 25 - 30 ℃; for 24h;

With hydrogenchloride; In ethyl acetate;

DOI:10.1016/j.tetasy.2016.03.012

Reference yield:

3-methyl-phenol (108-39-4) → bevantolol hydrochloride (42864-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water / 2 h / 60 °C

2: ethanol / 24 h / 25 - 30 °C

With sodium hydroxide; In ethanol; water;

DOI:10.1016/j.tetasy.2016.03.012

upstream raw materials:

m-tolyl glycidyl ether

2-(3,4-dimethoxyphenyl)-ethylamine

3-methyl-phenol

Downstream raw materials:

2-[(Z)-Hydroxyimino]-3-m-tolyloxy-propionaldehyde oxime

2-[(E)-Hydroxyimino]-3-m-tolyloxy-propionaldehyde oxime

1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-one oxime

1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-one oxime

Refernces

• 1、 Bredikhina, Zemfira A.,Zakharychev, Dmitry V.,Gubaidullin, Aidar T.,Bredikhin, Alexander A.. "One more chiral drug prone to spontaneous resolution: Binary phase diagram, absolute configuration, and crystal packing of bevantolol hydrochloride". experimental part. p. 171 - 176. Retrieved 2010/03/26.