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((Short description|Muscle relaxant))
((Use dmy dates|date=March 2023))
((Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402863818
| image = Vecuronium bromide.svg
| width = 250
| alt = 
| caption = 

<!-- Clinical data -->
| pronounce = 
| tradename = Norcuron, others
| Drugs.com = ((drugs.com|monograph|vecuronium_bromide))
| MedlinePlus = 
| DailyMedID = Vecuronium bromide
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment = 
| pregnancy_category = 
| routes_of_administration = [[Intravenous therapy|Intravenous]]
| class = 
| ATCvet = 
| ATC_prefix = M03
| ATC_suffix = AC03
| ATC_supplemental = 

<!-- Legal status -->
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| legal_BR_comment = 
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = 
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 100% (IV)
| protein_bound = 
| metabolism = liver 30%
| metabolites = 
| onset = < 1 min<ref name=AHFS2016/>
| elimination_half-life = 51–80 minutes (longer with [[kidney failure]])
| duration_of_action = 15–30 min<ref name=Ric2015>((cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=23))</ref>
| excretion = Fecal (40–75%) and [[kidney]] (30% as unchanged drug and [[metabolite]]s)

<!-- Identifiers -->
| CAS_number_Ref = ((cascite|correct|??))
| CAS_number = 50700-72-6
| CAS_supplemental = 
| PubChem = 39764
| IUPHAR_ligand = 
| DrugBank_Ref = ((drugbankcite|correct|drugbank))
| DrugBank = DB01339
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<!-- Chemical and physical data -->
| IUPAC_name = [(2''S'',3''S'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',16''S'',17''S'')-17-Acetyloxy-10,13-dimethyl-16-(1-methyl-3,4,5,6-tetrahydro-2''H''-pyridin-1-yl)-2-(1-piperidyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1''H''-cyclopenta[a]phenanthren-3-yl] acetate bromide
| C=34 | H=57 | N=2 | O=4 | Br=1
| SMILES = 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-]
| StdInChI_Ref = ((stdinchicite|changed|chemspider))
| StdInChI = 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
| StdInChI_comment = 
| StdInChIKey_Ref = ((stdinchicite|changed|chemspider))
| StdInChIKey = VEPSYABRBFXYIB-PWXDFCLTSA-M
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
))

<!-- Definition and medical uses -->
'''Vecuronium bromide''', sold under the brand name '''Norcuron''' among others, is a medication used as part of [[general anesthesia]] to provide [[skeletal muscle relaxation]] during [[surgery]] or [[mechanical ventilation]].<ref name=AHFS2016/> It is also used to help with [[endotracheal intubation]]; however, agents such as [[suxamethonium]] (succinylcholine) or [[rocuronium]] are generally preferred if this needs to be done quickly.<ref name=AHFS2016/> It is given by [[intravenous|injection into a vein]].<ref name=AHFS2016/> Effects are greatest at about 4 minutes and last for up to an hour.<ref name=AHFS2016/>

<!-- Side effects and mechanism -->
Side effects may include [[low blood pressure]] and prolonged [[paralysis]].<ref>((cite web|title=NORCURON 10mg - Summary of Product Characteristics (SPC) - (eMC)|url=https://www.medicines.org.uk/emc/medicine/1398|website=www.medicines.org.uk|access-date=16 December 2016|date=4 August 2000|url-status=live|archive-url=https://web.archive.org/web/20161220191806/https://www.medicines.org.uk/emc/medicine/1398|archive-date=20 December 2016))</ref> [[Allergic reactions]] are rare.<ref name=WHO2008>((cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization |page=431 ))</ref> It is unclear if use in [[pregnancy]] is safe for the baby.<ref name=AHFS2016/>

Vecuronium is in the [[aminosteroid]] [[neuromuscular-blocker]] family of medications and is of the [[non-depolarizing]] type.<ref name=AHFS2016/> It works by [[ Receptor antagonist|competitively blocking]] the action of [[acetylcholine]] on [[skeletal muscles]].<ref name=AHFS2016/> The effects may be reversed with [[sugammadex]] or a combination of [[neostigmine]] and [[glycopyrrolate]]. To minimize residual blockade, reversal should only be attempted if some degree of spontaneous recovery has been achieved.<ref name=AHFS2016/>

<!-- History, society and culture -->
Vecuronium was approved for medical use in the United States in 1984<ref name=AHFS2016>((cite web|title=Vecuronium Bromide|url=https://www.drugs.com/monograph/vecuronium-bromide.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221012535/https://www.drugs.com/monograph/vecuronium-bromide.html|archive-date=21 December 2016))</ref> and is available as a [[generic medication]].<ref name=AHFS2016/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">((cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free ))</ref><ref name="WHO22nd">((cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free ))</ref>

== Mechanism of action ==
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.((medcn|date=February 2023)) Under [[balanced 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.((medcn|date=February 2023)) The neuromuscular blocking action of vecuronium is slightly enhanced in the presence of potent inhalation anesthetics.((medcn|date=February 2023)) If vecuronium is first administered more than 5 minutes after the start of the inhalation of [[enflurane]], [[isoflurane]], or [[halothane]], or when a [[steady state]] has been achieved, the intubating dose of vecuronium may be decreased by approximately 15%.((medcn|date=February 2023))

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 with [[kidney failure]].<ref name="AHFS2016" />

Reversal of vecuronium can be accomplished by administration of [[sugammadex]] which is a γ-[[cyclodextrin]] which encapsulates vecuronium preventing it from binding to receptors.<ref>((Cite web|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022225lbl.pdf|title=Bridion (sugammadex) Injection|last=U.S. Food and Drug Administration|access-date=1 December 2019))</ref> Reversal can also be accomplished with [[neostigmine]] or other [[cholinesterase inhibitor]]s, but their efficacy is lower than that of sugammadex.<ref>((cite journal | vauthors = Carron M, Zarantonello F, Tellaroli P, Ori C | title = Efficacy and safety of sugammadex compared to neostigmine for reversal of neuromuscular blockade: a meta-analysis of randomized controlled trials | journal = Journal of Clinical Anesthesia | volume = 35 | pages = 1–12 | date = December 2016 | pmid = 27871504 | doi = 10.1016/j.jclinane.2016.06.018 ))</ref>

==History==
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 a [[Llanero]] 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.<ref>((Cite book|url=https://archive.org/details/scenesinsouthamer00pezr|title=Wild Scenes in South America, Or, Life in the Llanos of Venezuela| vauthors = Páez R |date=1 January 1862|publisher=C. Scribner|pages=[https://archive.org/details/scenesinsouthamer00pezr/page/206 206]–208|quote=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))</ref> It is probable that the plant was ''[[Malouetia]] nitida'' or ''Malouetia schomburgki''.<ref name=":0">((cite journal | vauthors = McKenzie AG | title = Prelude to pancuronium and vecuronium | journal = Anaesthesia | volume = 55 | issue = 6 | pages = 551–556 | date = June 2000 | pmid = 10866718 | doi = 10.1046/j.1365-2044.2000.01423.x | s2cid = 22476701 | doi-access =  ))</ref>

The genus ''Malouetia'' (family ''[[Apocynaceae]]'') is found in both [[South America]] and [[Africa]]. The botanist Robert E. Woodson Jr comprehensively classified the American species of ''Malouetia'' in 1935. At that time, only one African species of ''Malouetia'' was recognized, but the following year Woodson described a second: ''Malouetia bequaertiana'', from the Belgian Congo.<ref name=":0" />

In 1960, scientists reported the isolation of [[malouetine]] from the roots and bark of ''Malouetia bequaertiana'' Woodson by means of an ion exchange technique. Optimization of the aminosteroid nucleus led to a sequence of synthesized derivatives, ultimately leading to [[pancuronium bromide]] in 1964. The name was derived from p(iperidino)an(drostane)cur(arising)-onium.<ref name=":0" />

A paper published in 1973 discussed the structure-activity relationships of a series of [[aminosteroid]] muscle relaxants, including the [[Neuromuscular-blocking drug#Pharmacokinetics|mono-quaternary]] analogue of pancuronium, later called vecuronium.<ref name=":0" />

==Society and culture==

Vecuronium bromide has been used as part of a drug cocktail that prisons in the [[Capital punishment in the United States|United States]] use for execution by [[lethal injection]]. Vecuronium is used to paralyze the prisoner and stop his or her breathing, in conjunction with a sedative and [[potassium 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.<ref>((cite news | url = https://www.nytimes.com/2014/04/30/us/oklahoma-executions.html | title = One Execution Botched, Oklahoma Delays the Next | date = 29 April 2014 | work = The New York Times | url-status = live | archive-url = https://web.archive.org/web/20140502042154/http://www.nytimes.com/2014/04/30/us/oklahoma-executions.html | archive-date = 2 May 2014 ))</ref>

In 2001, Japanese nurse [[Daisuke Mori]] was reported to have murdered 10 patients using vecuronium bromide.<ref>((cite news|url=http://www.expressindia.com/news/ie/daily/20010111/iin11054.html|title=Japanese nurse kills 10 patients, says wanted to trouble hospital|publisher=[[The Indian Express]]|date=10 January 2001|access-date=22 March 2008|url-status=dead|archive-url=https://web.archive.org/web/20120309151114/http://www.expressindia.com/news/ie/daily/20010111/iin11054.html|archive-date=9 March 2012))</ref> He was convicted of murder and was sentenced to [[life imprisonment]].<ref>((cite news|title=Nurse gets life for patient slaying|url=http://www.japantimes.co.jp/weekly/news/nn2004/nn20040410a6.htm|access-date=26 October 2011|newspaper=The Japan Times Weekly|date=10 April 2004|url-status=live|archive-url=https://web.archive.org/web/20100401130642/http://www.japantimes.co.jp/weekly/news/nn2004/nn20040410a6.htm|archive-date=1 April 2010))</ref>

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 the sedative [[midazolam]], also known as Versed.<ref>((cite news | url = https://www.npr.org/sections/health-shots/2022/03/25/1088902487/former-nurse-found-guilty-in-accidental-injection-death-of-75-year-old-patient | title = Former nurse found guilty in accidental injection death of 75-year-old patient | date = 25 March 2022 | work = NPR ))</ref>

== References ==
((Reflist))

== External links ==
* ((cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/vecuronium%20bromide | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Vecuronium Bromide ))

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