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HomeProduct name listCisatracurium besylate

Cisatracurium besylate

Synonym(s):Cisatracurium besylate

  • CAS NO.:96946-42-8
  • Empirical Formula: C53H72N2O12.2C6H5O3S
  • Molecular Weight: 1243.49
  • MDL number: MFCD00871018
  • EINECS: 620-579-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Cisatracurium besylate  Structural

What is Cisatracurium besylate ?

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.

Chemical properties

White Solid

Originator

Glaxo Wellcome (United Kingdom)

The Uses of Cisatracurium besylate

Cisatracurium Besylate is a nondepolarizing neuromuscular blocking agent, antagonizing the action of acetylcholine by inhibiting neuromuscular transmission.

The Uses of Cisatracurium besylate

An enantiomer of Atracurium Besylate (A794500). A neuromuscular blocking agent. It could be used in liver transplant patient with safety.

What are the applications of Application

Cisatracurium besylate is a neuromuscular blocking agent

Definition

ChEBI: The (1R,1'R,2R,2'R)-diastereoisomer of atracurium besylate. Commercial preparations of atracurium are mixtures of 10 stereoisomers, of which cisatracurium generally constitutes about 15%. isatracurium besylate is about 3 times more potent than the mixture of atracurium isomers as a neuromuscular blocking agent, and is used as a muscle relaxant for endotracheal intubation, to aid controlled ventilation, and in general anaesthesia.

Manufacturing Process

Acryloyl chloride (0.2 mole) in dry benzene (60 ml) was added over 0.5 hour to pentane-1,5-diol (0.1 mole), triehylamine (0.2 mole) and pyrogallol (0.1 g) in dry benzene (100 ml). Further dry benzene (100 ml) was added followed by triehylamine (10 ml), and the mixture stirred at 50°C for 0.5 hour. The triehylamine hydrochloride was filtered off and the solvent removed in vacuo to leave yellow oil which was distilled in the presence of a trace of pmethoxyphenol, excluding light, to give 1,5-pentamethylene diacrylate (12.9
g, 61%, b.p. 90-95°C/0.01 mm Hg). A solution of tetrahydropapaverine (4.43 g) and 1,5-pentamethylene diacrylate (1.30 g) in dry benzene (15 ml) was stirred under reflux for 48 hours, excluding light. The solvent was removed in vacuo and the residual pale red oil dissolved in chloroform (10 ml). Addition of ether (ca. 400 ml), followed by saturated ethereal oxalic acid solution (ca. 500 ml) gave a flocculent white precipitate, which was filtered off, washed with ether and dried. Crystallization (twice) from ethanol gave N,N'-4,10-dioxa-3,11- dioxodecylene-1,13-bis-tetrahydropapaverine dioxalate as a white powder (3.5 g, 51%, m.p. 117-121°C).
The free base N,N'-4,10-dioxa-3,11-dioxodecylene-1,13-bistetrahydropapaverine was obtained by basifying an aqueous solution of the dioxalate with sodium bicarbonate solution, followed by extraction with toluene and evaporation of the solvent, to give a colorless viscous oil.
Scrupulously dried base in spectroscopically pure acetonitrile was treated with benzenesulfonic acid at room temperature for 22 hours. The filtered reaction mixture was added dropwise to dry ether (ca. 450 ml). The flocculent white precipitate was filtered off, washed with dry ether, and dried in vacuo over P2O5 at 50°C to yield N,N'-4,10-dioxa-3,11-dioxodecylene-1,13-bistetrahydropapaverine dimesylate, a white powder with m.p. 104-112°C.

brand name

Nimbex (Abbott).

Therapeutic Function

Neuromuscular blocker

Properties of Cisatracurium besylate

Melting point: 90-93°C
storage temp.  Sealed in dry,Store in freezer, under -20°C
solubility  H2O: soluble1mg/mL
form  Powder
color  white

Safety information for Cisatracurium besylate

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for Cisatracurium besylate

InChIKey XXZSQOVSEBAPGS-UHFFFAOYSA-L

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