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Vecuronium bromide

From Wikipedia, the free encyclopedia
Muscle relaxant

Pharmaceutical compound
Vecuronium bromide
Clinical data
Trade namesNorcuron, others
AHFS/Drugs.comMonograph
License data
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% (IV)
Metabolismliver 30%
Onset of action< 1 min[1]
Eliminationhalf-life51–80 minutes (longer withkidney failure)
Duration of action15–30 min[2]
ExcretionFecal (40–75%) andkidney (30% as unchanged drug andmetabolites)
Identifiers
  • [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17S)-17-Acetyloxy-10,13-dimethyl-16-(1-methyl-3,4,5,6-tetrahydro-2H-pyridin-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 bromide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.051.549Edit this at Wikidata
Chemical and physical data
FormulaC34H57BrN2O4
Molar mass637.744 g·mol−1
3D model (JSmol)
  • CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1N4CCCCC4)C)CC[C@]5([C@H]3C[C@@H]([C@@H]5OC(=O)C)[N+]6(CCCCC6)C)C.[Br-]
  • InChI=1S/C34H57N2O4.BrH/c1-23(37)39-31-20-25-12-13-26-27(34(25,4)22-29(31)35-16-8-6-9-17-35)14-15-33(3)28(26)21-30(32(33)40-24(2)38)36(5)18-10-7-11-19-36;/h25-32H,6-22H2,1-5H3;1H/q+1;/p-1/t25-,26+,27-,28-,29-,30-,31-,32-,33-,34-;/m0./s1 ☒N
  • Key:VEPSYABRBFXYIB-PWXDFCLTSA-M ☒N
 ☒NcheckY (what is this?)  (verify)

Vecuronium bromide, sold under the brand nameNorcuron among others, is a medication used as part ofgeneral anesthesia to provideskeletal muscle relaxation duringsurgery ormechanical ventilation.[1] It is also used to help withendotracheal intubation; however, agents such assuxamethonium (succinylcholine) orrocuronium are generally preferred if this needs to be done quickly.[1] It is given byinjection into a vein.[1] Effects are greatest at about 4 minutes and last for up to an hour.[1]

Side effects may includelow blood pressure and prolongedparalysis.[3]Allergic reactions are rare.[4] It is unclear if use inpregnancy is safe for the fetus.[1]

Vecuronium is in theaminosteroidneuromuscular-blocker family of medications and is of thenon-depolarizing type.[1] It works bycompetitively blocking the action ofacetylcholine onskeletal muscles.[1] The effects may be reversed withsugammadex or a combination ofneostigmine andglycopyrrolate. To minimize residual blockade, reversal should only be attempted if some degree of spontaneous recovery has been achieved.[1]

Vecuronium was approved for medical use in the United States in 1984[1] and is available as ageneric medication.[1] It is on theWorld Health Organization's List of Essential Medicines.[5]

Mechanism of action

[edit]

Vecuronium operates by competing for the cholinoceptors at the motor end plate, thereby exerting its muscle-relaxing properties, which are used adjunctively to general anesthesia.[medical citation needed] Underbalanced anesthesia, the time to recovery to 25% of control (clinical duration) is approximately 25 to 40 minutes after injection and recovery is usually 95% complete approximately 45 to 65 minutes after injection of an intubating dose.[medical citation needed] The neuromuscular blocking action of vecuronium is slightly enhanced in the presence of potent inhalation anesthetics.[medical citation needed] If vecuronium is first administered more than 5 minutes after the start of the inhalation ofenflurane,isoflurane, orhalothane, or when asteady state has been achieved, the intubating dose of vecuronium may be decreased by approximately 15%.[medical citation needed]

Vecuronium has an active metabolite, 3-desacetyl-vecuronium, that has 80% of the effect of vecuronium. Accumulation of this metabolite, which is cleared by the kidneys, can prolong the duration of action of the drug, particularly when an infusion is used in a person withkidney failure.[1]

Reversal of vecuronium can be accomplished by administration ofsugammadex which is a γ-cyclodextrin which encapsulates vecuronium preventing it from binding to receptors.[6] Reversal can also be accomplished withneostigmine or othercholinesterase inhibitors, but their efficacy is lower than that of sugammadex.[7]

History

[edit]

As long ago as 1862, adventurer Don Ramon Paez described a Venezuelan poison,guachamaca, which the indigenous peoples used to lace sardines as bait for herons and cranes. If the head and neck of a bird so killed was cut off, the remainder of the flesh could be eaten safely. Paez also described the attempt of aLlanero woman to murder a rival to her lover's affections with guachamaca and unintentionally killed 10 other people when her husband shared his food with their guests.[8] It is probable that the plant wasMalouetia nitida orMalouetia schomburgki.[9]

The genusMalouetia (familyApocynaceae) is found in bothSouth America andAfrica. The botanist Robert E. Woodson Jr comprehensively classified the American species ofMalouetia in 1935. At that time, only one African species ofMalouetia was recognized, but the following year Woodson described a second:Malouetia bequaertiana, from the Belgian Congo.[9]

In 1960, scientists reported the isolation ofmalouetine from the roots and bark ofMalouetia bequaertiana Woodson by means of an ion exchange technique. Optimization of the aminosteroid nucleus led to a sequence of synthesized derivatives, ultimately leading topancuronium bromide in 1964. The name was derived from p(iperidino)an(drostane)cur(arising)-onium.[9]

A paper published in 1973 discussed the structure-activity relationships of a series ofaminosteroid muscle relaxants, including themono-quaternary analogue of pancuronium, later called vecuronium.[9]

Society and culture

[edit]

Vecuronium bromide has been used as part of a drug cocktail that prisons in theUnited States use for execution bylethal injection. Vecuronium is used to paralyze the prisoner and stop his or her breathing, in conjunction with a sedative andpotassium chloride to stop the prisoner's heart. Injections of vecuronium bromide without proper sedation allow the person to be fully awake but unable to move in response to pain.[10]

In 2001, Japanese nurseDaisuke Mori was reported to have murdered 10 patients using vecuronium bromide.[11] He was convicted of murder and was sentenced tolife imprisonment.[12]

In 2022,Vanderbilt University Medical Center nurse RaDonda Vaught was convicted of two felony charges in the death of a patient who was mistakenly administered vecuronium bromide, rather than thesedativemidazolam, also known as Versed.[13]

References

[edit]
  1. ^abcdefghijkl"Vecuronium Bromide". The American Society of Health-System Pharmacists.Archived from the original on 21 December 2016. Retrieved8 December 2016.
  2. ^Hamilton R (2015).Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 23.ISBN 9781284057560.
  3. ^"NORCURON 10mg - Summary of Product Characteristics (SPC) - (eMC)".www.medicines.org.uk. 4 August 2000.Archived from the original on 20 December 2016. Retrieved16 December 2016.
  4. ^World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.).WHO Model Formulary 2008. World Health Organization. p. 431.hdl:10665/44053.ISBN 9789241547659.
  5. ^World Health Organization (2023).The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization.hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  6. ^U.S. Food and Drug Administration."Bridion (sugammadex) Injection"(PDF). Archived fromthe original(PDF) on 7 February 2016. Retrieved1 December 2019.
  7. ^Carron M, Zarantonello F, Tellaroli P, Ori C (December 2016). "Efficacy and safety of sugammadex compared to neostigmine for reversal of neuromuscular blockade: a meta-analysis of randomized controlled trials".Journal of Clinical Anesthesia.35:1–12.doi:10.1016/j.jclinane.2016.06.018.PMID 27871504.
  8. ^Páez R (1 January 1862).Wild Scenes in South America, Or, Life in the Llanos of Venezuela. C. Scribner. pp. 206–208.A dreadful case of poisoning by means of this plant had just occurred at Nutrias soon after our arrival on the Apure which created for a time great excitement even amidst that scattered population
  9. ^abcdMcKenzie AG (June 2000). "Prelude to pancuronium and vecuronium".Anaesthesia.55 (6):551–556.doi:10.1046/j.1365-2044.2000.01423.x.PMID 10866718.S2CID 22476701.
  10. ^"One Execution Botched, Oklahoma Delays the Next".The New York Times. 29 April 2014.Archived from the original on 2 May 2014.
  11. ^"Japanese nurse kills 10 patients, says wanted to trouble hospital".The Indian Express. 10 January 2001. Archived fromthe original on 9 March 2012. Retrieved22 March 2008.
  12. ^"Nurse gets life for patient slaying".The Japan Times Weekly. 10 April 2004.Archived from the original on 1 April 2010. Retrieved26 October 2011.
  13. ^"Former nurse found guilty in accidental injection death of 75-year-old patient".NPR. 25 March 2022.

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