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Vecuronium bromide

Basic information Description References Safety Supplier Related

Vecuronium bromide Basic information

Product Name:
Vecuronium bromide
Synonyms:
  • norcuron
  • [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetoxy-10,13-dimethyl-16-(1-methylpiperidin-1-ium-1-yl)-2-(1-piperidyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  • 1-[(2Beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl]-1-methylpiperidinium bromide hydrate
  • 1-(3-alpha,17-beta-diacetoxy-2-beta-piperidino-5-alpha-androstan-piperidiniu
  • 17beta-diol,16beta-pipecolinio-2beta-piperidino-5alpha-androstan-3alphbro
  • mide,diacetate
  • nc-45
  • orgnc45
CAS:
50700-72-6
MF:
C34H57BrN2O4
MW:
637.73138
EINECS:
256-723-9
Product Categories:
  • CAMPRAL
  • API
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroid and Hormone
  • Pharmaceutical material and intermeidates
  • Organics
  • Neuromuscular blocking agent
  • Steroids
  • Acetylcholine receptor
  • APIs
Mol File:
50700-72-6.mol
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Vecuronium bromide Chemical Properties

Melting point:
227-229°C
alpha 
+30.5~+35.0゜(D/20℃)(c=0.5,dil.HCl)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Slightly soluble in water, freely soluble in methylene chloride, sparingly soluble in acetonitrile and in anhydrous ethanol.
form 
neat
color 
White
Merck 
14,9941
BRN 
4837308
Stability:
Hygroscopic
InChIKey
VEPSYABRBFXYIB-PWXDFCLTSA-M
CAS DataBase Reference
50700-72-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-22
Safety Statements 
26-37/39
WGK Germany 
3
RTECS 
TN4875000
HS Code 
2933399090
Toxicity
LD50 in mice: 0.061 mg/kg i.v. (Buckett)
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Vecuronium bromide Usage And Synthesis

Description

Vecuronium bromide (Brand name: Norcuron) is a drug which can be supplied to general anesthesia to keep skeletal muscle relaxation during the surgery or mechanical ventilation. It can also be used to help with endotracheal intubation. It has rapid onset (within 4 minutes) and has its effect last for 4 hour. Its mechanism of action is through competitively binding to the nicotinic cholinergic receptors, further antagonizing the opportunity for acetylcholine from binding to the nicotinic receptor at the postjunctional membrane of the myoneural junction. This process prevents the depolarization and the release of calcium ions, stopping muscle contraction and help muscle relaxation.

References

https://en.wikipedia.org/wiki/Vecuronium_bromide
https://www.drugbank.ca/drugs/DB01339  

Description

Vecuronium, 1-[(2β,3α,5α,16β,17β,)-3,17-bis(acetyloxy)-2-(1-piperidinyl) androstan-16-yl]-1-methylpiperidinium bromide (15.1.9), differs from panuronium only in the extent of alkylation. Only the piperidine substituent on C16 of the steroid skeleton is transformed into a quaternary salt.

Description

Vecuronium is a non-depolarizing muscle relaxant derived from the aminosteroid pancuronium and used adjunctively to general anesthesia. It competitively blocks cholinergic receptors at the motor end plate of the neuromuscular junction, inducing temporary paralysis. In humans, it has been shown to reduce muscle twitch tension with an ED50 value of 0.15 mg/kg for a duration of 27 minutes without inducing cardiovascular effects.

Chemical Properties

White Solid

Uses

alcohol antagonist

Uses

An aminosteroid, competitive neuromuscular blocker agent.

Definition

ChEBI: The organic bromide salt of a 5alpha-androstane compound having 3alpha-acetoxy-, 17beta-acetoxy-, 2beta-piperidinino- and 16beta-N-methylpiperidinium su stituents.

brand name

Norcuron (Organon).

Biological Functions

Vecuronium bromide (Norcuron) is chemically identical to pancuronium except for a tertiary amine in place of a quaternary nitrogen. However, some of the drug will exist as the bisquaternary compound, depending on body pH. Vecuronium has a moderate onset of action (2.4 minutes) and a duration of effect of about 50 minutes. Like pancuronium, it does not block ganglia or vagal neuroeffector junctions, does not release histamine, and is eliminated by urinary excretion.

General Description

Vecuronium bromide, 1-(3 ,17 -dihydroxy-2 -piperidino-5 -androstan-16 -yl)-1-methylpiperidinium bromide diacetate (Norcuron), is themonoquaternary analog of pancuronium bromide. It belongsto the class of nondepolarizing neuromuscular blockingagents and produces effects similar to those of drugs in thisclass. It is unstable in the presence of acids and undergoesgradual hydrolysis of its ester functions in aqueous solution.Aqueous solutions have a pH of about 4.0.

Pharmacology

Vecuronium bromide is steroidal agent that was developed in an attempt to reduce the cardiovascular effects of pancuronium. I t is similar in structure to the older drug, differing only in the loss of a methyl group from one quaternary ammonium radical. Thus it is a monoquaternary amine. An intubating dose of 0.1mgkg-1 produces profound neuromuscular block within 3min. This dose produces clinical block for about 30min. Vecuronium rarely produces histamine release, nor does it have any direct cardiovascular effects, although it allows the cardiac effects of other anaesthetic agents, such as bradycardia produced by the opioids, to go unchallenged. Vecuronium is excreted through the kidneys (30%), although to a lesser extent than pancuronium, and undergoes hepatic deacetylation; the deacetylated metabolites have neuromuscular blocking properties. Repeated doses should be used with care in patients with renal or hepatic disease because they accumulate.

Clinical Use

Vecuronium Bromide is usedmainly to produce skeletal muscle relaxation during surgeryand to assist in controlled respiration after general anesthesiahas been induced.

Veterinary Drugs and Treatments

Vecuronium is indicated as an adjunct to general anesthesia to produce muscle relaxation during surgical procedures or mechanical ventilation and to facilitate endotracheal intubation. It causes very minimal cardiac effects and generally does not cause the release of histamine.

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced muscle relaxant effect.
Anti-arrhythmics: procainamide enhances muscle relaxant effect.
Antibacterials: effect enhanced by aminoglycosides, clindamycin, polymyxins and piperacillin.
Antiepileptics: muscle relaxant effects antagonised by carbamazepine; effects reduced by long-term use of fosphenytoin and phenytoin but might be increased by acute use.
Botulinum toxin: neuromuscular block enhanced (risk of toxicity).

Metabolism

Vecuronium partly metabolised by the liver; the metabolites have some neuromuscular blocking activity. It is excreted mainly in bile as unchanged drug and metabolites; some is also excreted in the urine.

Vecuronium bromide Preparation Products And Raw materials

Raw materials

Vecuronium bromideSupplier

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