Editing Vecuronium bromide (section)

{{Short description|Muscle relaxant}}
{{Use dmy dates|date=March 2023}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402863818
| image = Vecuronium bromide.svg
| image_class = skin-invert-image
| 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 -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment = 
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| 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
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 36357
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 7E4PHP5N1D
| KEGG = D00767
| ChEBI = 
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201219
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 

<!-- 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="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>