Atracurium besylate

Base Information

• Chemical Name: Atracurium besylate
• CAS No.: 64228-81-5
• Molecular Formula: C53H72N2O12^.2(C6H5O3S)
• Molecular Weight: 1243.5
• Hs Code.: 29334900
• Mol file: 64228-81-5.mol

Synonyms:Tracrium;Atracurii besilas [INN-Latin];Atracurium Besilate injection;Besilate datracurium [INN-French];Isoquinolinium, 2,2-(1,5-pentanediylbis(oxy(3-oxo-3,1-propanediyl)))bis(1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, dibenzenesulfonate;Atracurium besilate;Track detectorsTracrium;BW 33A;Tracrium (TN);Besilato de atracurio [INN-Spanish];Atracurium besylate (USP);Atracurii besilas;Atracurium besy;

Chemical Property of Atracurium besylate

Chemical Property:

• Appearance/Colour: White to yellowish-white powder
• Melting Point: 85-90 °C
• PSA: 257.60000
• LogP: 11.32610
• Storage Temp.: 2-8°C
• Solubility.: H2O: ~27 mg/mL

Purity/Quality:

98% up ^*data from raw suppliers

Atracurium besylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1. It is a kind of non-depolarizing muscle relaxants with the 2.5 times of effect as high as tubocurarine 2.5 times but with a short duration. It is used for a variety of surgical procedures, especially for intubation and caesarean section. 2. It is a skeletal muscle relaxant for general anesthesia. A neuromuscular blocking agent antibacterial
• Therapeutic Function: Neuromuscular blocker
• Biological Functions: Atracurium besylate (Tracrium) is a benzylisoquinolinium compound like d-tubocurarine. Its actions are similar to those of d-tubocurarine, but its duration of action is shorter (45 minutes) because of spontaneous degradation of the molecule (Hofmann elimination). Because of this, atracurium is useful in patients with low or atypical plasma cholinesterase and in patients with renal or hepatic impairment.
• Clinical Use: Atracurium Besylate is metabolized rapidly and nonenzymatically to yield laudanosineand a smaller quaternary compound ,which do not have neuromuscular blocking activity. In vitroexperiments show that atracurium besylate breaks down atpH 7.4 and 37°C by a Hoffman elimination reaction.Atracurium besylate undergoes enzymatic decompositionof its ester function to yield an inactive quaternary alcoholand quaternary acid. AChE inhibitors such as neostigmine,edrophonium, and pyridostigmine antagonize paralysis byatracurium besylate.
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: effects enhanced by ketamine; enhanced effect with volatile liquid general anaesthetics. Anti-arrhythmics: procainamide enhances muscle relaxant effect. Antibacterials: aminoglycosides, clindamycin, polymyxin and piperacillin enhance effect of atracurium. Antiepileptics: muscle relaxant effects antagonised by carbamazepine; effects reduced by long-term use of phenytoin but might be increased by acute use. Atracurium enhances the neuromuscular block produced by botulinum toxin (risk of toxicity)

Technology Process of Atracurium besylate

There total 12 articles about Atracurium besylate 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: 85.4%

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine (64228-84-8) + Methyl benzenesulfonate (80-18-2) → cisatracurium besylate (64228-81-5,96946-42-8,96946-44-0,96946-46-2,96946-48-4,96946-50-8,96946-52-0,96946-54-2,96946-56-4,96946-58-6,96946-60-0)

Guidance literature:

In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 24h;

Reference yield: 85.0%

pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4) + Methyl benzenesulfonate (80-18-2) → atracurium besylate (64228-81-5)

Guidance literature:

In acetonitrile; for 48h; Ambient temperature;

Reference yield:

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → atracurium besylate (64228-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / 2 h / 190 - 210 °C

2: phosphoryl chloride / toluene / 3 h / Heating

3: 71 percent / sodium borohydride / 19 h / Ambient temperature

4: 51 percent / benzene / 48 h / Heating

5: 85 percent / acetonitrile / 48 h / Ambient temperature

With sodium tetrahydroborate; trichlorophosphate; In toluene; acetonitrile; benzene;

upstream raw materials:

pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate

Methyl benzenesulfonate

(3,4-Dimethoxyphenyl)acetic acid

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF CISATRACURIUM BESYLATE". Page/Page column 8; 12. . Retrieved 2010/11/18.
• 2、 Stenlake,Waigh,Dewar,et al.. "Biodegradable neuromuscular blocking agents. Part 4. Atracurium besylate and related polyalkylene di-esters". . p. 515 - 524. Retrieved 2007/10/02.