Cisatracurium besylate

Bezeichnung:Cisatracurium besylate

CAS-Nr96946-42-8

Englisch Name:Cisatracurium besylate

CBNumberCB7855410

SummenformelC53H72N2O12.2C6H5O3S

Molgewicht1243.49

MOL-Datei96946-42-8.mol

Cisatracurium besylate physikalisch-chemischer Eigenschaften

Schmelzpunkt	90-93°C
storage temp.	Sealed in dry,Store in freezer, under -20°C
Löslichkeit	H2O: soluble1mg/mL
Aggregatzustand	Powder
Farbe	white
InChIKey	XXZSQOVSEBAPGS-UHFFFAOYSA-L

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-36
S-Sätze:	45
RIDADR	UN 2811 6.1 / PGIII
WGK Germany	3
HS Code	29145090

Gefahreninformationscode (GHS)

Cisatracurium besylate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
White Solid
Originator
Glaxo Wellcome (United Kingdom)
Verwenden
An enantiomer of Atracurium Besylate (A794500). A neuromuscular blocking agent. It could be used in liver transplant patient with safety.
Verwenden
Cisatracurium Besylate is a nondepolarizing neuromuscular blocking agent, antagonizing the action of acetylcholine by inhibiting neuromuscular transmission.
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.
Trademarks
Nimbex (Abbott).
Therapeutic Function
Neuromuscular blocker

Cisatracurium besylate Upstream-Materialien And Downstream Produkte

Cisatracurium besylate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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