Cisatracurium besylate

Base Information

• Chemical Name: Cisatracurium besylate
• CAS No.: 96946-42-8
• Molecular Formula: 2C₆H₅O₃S*C₅₃H₇₂N₂O₁₂
• Molecular Weight: 1243.5
• Hs Code.: 29145090
• Mol file: 96946-42-8.mol

Synonyms:(1R,2R)-2-(2-Carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium benzenesulfonate, pentamethylene ester;51W89;Nimbex (TN);Cisatracurium besylate [USAN:BAN];benzenesulfonate; 5-[3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propanoyloxy]pentyl 3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propanoate;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-,(1R,1'R,2R,2'R)-,dibenzenesulfonate;Nimbex;Atracurium besylate 1R-cis,1R-cis form;Cisatracurium besylate (USAN);Cisatracurium Besilate(96946-42-8);1R-cis,1R′-cis (Cisatracurium Besylate);

Chemical Property of Cisatracurium besylate

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 90-93 °C
• PSA: 257.60000
• LogP: 11.32610
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: soluble1mg/mL

Purity/Quality:

99%min ^*data from raw suppliers

CisatracuriumBesylate(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Interactions: 1. when combined with a variety of anesthetics, ganglion blockers (such as six methylamine), potent diuretics, antiarrhythmic drugs, and other polypeptide antibiotics tetracycline, the muscle relaxation effect can be extended or strengthened. 2. Drug which can interfere with potassium, magnesium, lithium salt balance, and potassium releasing hormones can change the muscle relaxing effect of this product. 3. the application of succinylcholine can cause that the drug’s effect can’t be antagonized by neostigmine.
• Description: Cisatracurium besylate is a new intermediate-duration non-depolarizing muscle relaxant launched in the U.S.A. for intubation and maintenance of muscle relaxation during surgery and intensive care. Cisatracurium besylate is the single 1 R cis-1'R cis isomer of the commercial preparation of atracurium, a mixture of 10 isomers. It is 3 to 5 times more potent than the mixture with similar onset and duration of action. The single isomer was also reported to have reduced propensity to release histamine and have a stable cardiovascular profile. Similar to structurally related mivacurium, cisatracurium has distinct advantages of rapid degradation, enzymatic metabolism that is independent of liver or kidney resulting in short duration of action and fast, complete recovery.
• Uses: Cisatracurium Besylate is a nondepolarizing neuromuscular blocking agent, antagonizing the action of acetylcholine by inhibiting neuromuscular transmission. An enantiomer of Atracurium Besylate (A794500). A neuromuscular blocking agent. It could be used in liver transplant patient with safety.

Technology Process of Cisatracurium besylate

There total 5 articles about Cisatracurium 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:

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4) + 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:

With sodium hydrogencarbonate; In acetonitrile; at 20 - 25 ℃; for 48h;

Reference yield:

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride (5884-22-0) → 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:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; zinc(II) chloride; (2S,3S)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid / tetrahydrofuran / 21 h / 20 °C / Inert atmosphere; Reflux

2.1: acetic acid / toluene / 4 h / 80 °C

2.2: 1 h / 20 °C

3.1: sodium hydroxide / water; dichloromethane / 0.25 h / 20 °C / pH 9 - 10

3.2: 2 h / 8 - 12 °C / 760.05 Torr

4.1: acetic acid; cobalt(II) chloride hexahydrate / acetonitrile / 12 h / 60 °C

5.1: dichloromethane; dimethyl sulfoxide / 24 h / 20 °C

With sodium tetrahydroborate; (2S,3S)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid; cobalt(II) chloride hexahydrate; acetic acid; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;

upstream raw materials:

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate

Methyl benzenesulfonate

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF CISATRACURIUM BESYLATE". Page/Page column 8; 12. . Retrieved 2010/11/18.