Levalbuterol

Base Information

• Chemical Name: Levalbuterol
• CAS No.: 34391-04-3
• Molecular Formula: C13H21NO3
• Molecular Weight: 239.315
• Hs Code.: 2922509090
• European Community (EC) Number: 608-983-3
• UNII: EDN2NBH5SS
• DSSTox Substance ID: DTXSID80187964
• Nikkaji Number: J428.072E
• Wikipedia: Levosalbutamol
• Wikidata: Q408709
• NCI Thesaurus Code: C74196
• RXCUI: 237159
• Pharos Ligand ID: RJYK5TFF2UX8
• Metabolomics Workbench ID: 37943
• ChEMBL ID: CHEMBL1002
• Mol file: 34391-04-3.mol

Synonyms:Hydrochloride, Levalbuterol;Hydrochloride, Levosalbutamol;Levalbuterol;Levalbuterol Hydrochloride;Levosalbutamol Hydrochloride;Xopenex

Chemical Property of Levalbuterol

Chemical Property:

• Vapor Pressure: 2.78E-08mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 433.478 °C at 760 mmHg
• PKA: 9.99±0.31(Predicted)
• Flash Point: 159.519 °C
• PSA: 72.72000
• Density: 1.153 g/cm³
• LogP: 1.69690
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 239.15214353
• Heavy Atom Count: 17
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

LEVALBUTEROL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=CC(=C(C=C1)O)CO)O
• Isomeric SMILES: CC(C)(C)NC[C@@H](C1=CC(=C(C=C1)O)CO)O
• Recent ClinicalTrials: A Pilot Study to Determine the Most Effective Dose of Arformoterol for Treating Acute Asthmatic Patients
• Recent EU Clinical Trials: A proof of concept study to evaluate rebound trough airway hyper-responsiveness after single and chronic dosing with levosalbutamol and racemic salbutamol in persistent asthmatics
• Description: Salbutamol is a bronchodilator medication that eases muscle tension in the airways adjoining with the lungs and enhances the flow of air circulating through the lungs. It is a short-acting medication that is used in the treatment of acute bronchopulmonary disorders which may include chronic obstructive pulmonary disorders (COPD), and chronic instances of bronchospasm resultant of acute bronchitis and bronchial asthma. It can also be used for the prophylactic treatment of training-induced bronchospasm. Salbutamol indicates 29 times more selectivity for beta2 receptors as compared to beta1 receptors, which gives it a higher specificity for adrenergic receptors positioned in the heart. Salbutamol comprises a racemic combination of Sand Risomers, where the R-isomer illustrates a higher affinity (about 150 times more) than the S-isomer, which is directly linked to increased toxicity. This has also influenced the development of levalbuterol. Levalbuterol was launched in the US for the treatment or prevention of bronchospasm in patients with reversible obstructive airway disease. It is the single R-enantiomer version of racemic albuterol (salbutamol) marketed for more than 30 years as a mainstay in the treatment of asthma. The R-isomer can be obtained with an excellent optical purity by enantiomeric purification based on the separation of diastereomeric tartrates. This isomer retains solely the desired bronchodilating effect of the racemic mixture due to a potent agonistic effect on β2-adrenoceptors, with a lower incidence of β- mediated side effects such as pulse rate increase, tremor and decrease in blood glucose and potassium levels. A pivotal clinical trial with two doses of levalbuterol and racemic albuterol, given by nebulization, demonstrated a greater improvement in lung function for the pure enantiomer levalbuterol.
• Indications: Salbutamol is indicated for the treatment of chronic asthma, maintenance of asthma, bronchitis, chronic obstructive pulmonary disease and uncomplicated preterm labor. Salbutamol is an adrenergic bronchodilator, which is a class of medications that are inhaled through the mouth to ease tension in the bronchial tubes and the lungs. Such drugs also relieve shortness of breath, coughs, breathing complications, and wheezing by enhancing the circulation of air through the air passages.
• Drug Interactions: Salbutamol may be prescribed alongside other medications depending on the condition of the patient and the effectiveness of the drug combination. However, Salbutamol may enhance the occurrence of certain side effects if it is combined with Trimipramine, Tianeptine, Opipramol, Protriptyline, Nortriptyline, Melitracen, Lofepramine, Levalbuterol, Imipramine, Doxepin, Dibenzepin, Desipramine, Clomipramine, Atomoxetine, Amoxapine, Amitriptylinoxide, Amitriptyline and Amineptine. This list is not all-inclusive hence one should also consult their doctor for dose adjustments.
• Uses: (R)-Salbutamol is used in composition and methods to reduce beta-agonist-mediated tachyphylaxis. Salbutamol is the β2-agonist used most commonly for the prevention and treatment of bronchospasm. I t is most commonly administered in its inhaled form by metered-dose inhaler (1–2 puffs of 100μg each) or via nebuliser in more severe cases of bronchospasm (2.5–5mg). In patients with lifethreatening asthma it may be administered i.v. as both a bolus (250μg) and infusion (3–20μgmin –1). Intravenous administration requires cardiac monitoring as tachyarrhythmias may be significant. Salbutamol may also be used in the management of hyperkalaemia, temporarily driving K+ intracellularly via stimulation of the Na+–K+ ATPase pump.
• Therapeutic Function: Bronchodilator
• Clinical Use: Beta2 -adrenoceptor agonist: Reversible airways disease
• Drug interactions: Potentially hazardous interactions with other drugs Increased risk of hypokalaemia when diuretics, theophylline or large doses of corticosteroids are given with high doses of salbutamol. Antihypertensives: acute hypotension with IV infusion of salbutamol and methyldopa.

Technology Process of Levalbuterol

There total 15 articles about Levalbuterol 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: 99.0%

(R)-2-(N-tert-butylamino)-1-(2,2-dimethyl-4H-benzo[3,4-e]1,3-dioxin-6-yl)ethanol (238762-31-7) → Levalbuterol (34391-04-3,34271-50-6)

Guidance literature:

With sulfuric acid; In methanol; at 21 ℃;

Reference yield: 92.5%

(R)-α1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol D-dibenzoyltartrate (348135-26-2) → Levalbuterol (34391-04-3,34271-50-6)

Guidance literature:

With hydrogenchloride; In methanol; ethyl acetate; at -2 - 2 ℃; for 1.25h; Product distribution / selectivity;

Reference yield: 92.3%

methanol (67-56-1) + (R)-α1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol D-dibenzoyltartrate (348135-26-2) → N-(tert-butyl)-2-methoxy-2-(4-hydroxy-3-(hydroxymethyl)phen-1-yl)-ethanamine (870076-72-5) + SLB-OMe prim (18910-70-8) + Levalbuterol (34391-04-3,34271-50-6)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at -2 - 2 ℃; for 1.25 - 2h; Product distribution / selectivity;

upstream raw materials:

(R)-2-(N-tert-butylamino)-1-(2,2-dimethyl-4H-benzo[3,4-e]1,3-dioxin-6-yl)ethanol

(R)-α1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol D-dibenzoyltartrate

methanol

tert-butylamine

Downstream raw materials:

levosalbutamol hydrochloride

Refernces

• 1、 -. "Preparing method of levalbuterol". Paragraph 0106; 0107; 0108; 0109; 0110; 0111; 0112; 0113-14. . Retrieved 2017/04/29.
• 2、 Wang, Zhaokun,Zhang, Qiongwen,Luo, Linda,Sun, Tiemin,Guo, Xingjie. "Comparison of three S-β-CDs with different degrees of substitution for the chiral separation of 12 drugs in capillary electrophoresis". . p. 558 - 565. Retrieved 2017/08/26.