Rocuronium bromide

{{Short description|Non-depolarizing neuromuscular blocker}} {{Use mdy dates|date=September 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | caption2 = 3D representation of a rocuronium molecule | verifiedrevid = 391923978 | image = Rocuronium.svg | image_class = skin-invert-image | width = 250 | alt =  | caption = Molecular structure of rocuronium | image2 = Rocuronium 3D.png | image_class2 = bg-transparent | tradename = Esmeron, Zemuron | Drugs.com = {{drugs.com|monograph|rocuronium_bromide}} | pregnancy_category = | routes_of_administration = Intravenous | ATC_prefix = M03 | ATC_suffix = AC09

| legal_AU = S4 | legal_AU_comment = <ref>{{Cite web | title=ROCURONIUM-HAMELN (Hameln Pharma Pty Ltd) {{!}} Therapeutic Goods Administration (TGA) | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/rocuronium-hameln-hameln-pharma-pty-ltd | archive-url=https://web.archive.org/web/20240915052232/https://www.tga.gov.au/resources/prescription-medicines-registrations/rocuronium-hameln-hameln-pharma-pty-ltd | access-date=2025-08-25 | archive-date=2024-09-15}}</ref> | legal_BR =  | legal_BR_comment = | legal_CA =  | legal_CA_comment = | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US =  | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN =  | legal_UN_comment = | legal_status =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 119302-91-9 | IUPHAR_ligand = 4003 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = DB00728 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = I65MW4OFHZ | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1201244 | PubChem = 441351 | KEGG = D00765 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 390104

| IUPAC_name = 1-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetoxy-3-hydroxy-10,13-dimethyl-2-morpholinohexadecahydro-1H-cyclopenta[a]phenanthren-16-yl)-1-allylpyrrolidinium bromide | C = 32 | H = 53 | N = 2 | O = 4 | Br = 1 | SMILES = CC(=O)O[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@@H]([C@H](C4)O)N5CCOCC5)C)C)[N+]6(CCCC6)CC=C.[Br-] | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C32H53N2O4.BrH/c1-5-14-34(15-6-7-16-34)28-20-26-24-9-8-23-19-29(36)27(33-12-17-37-18-13-33)21-32(23,4)25(24)10-11-31(26,3)30(28)38-22(2)35;/h5,23-30,36H,1,6-21H2,2-4H3;1H/q+1;/p-1/t23-,24+,25-,26-,27-,28-,29-,30-,31-,32-;/m0./s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = OYTJKRAYGYRUJK-FMCCZJBLSA-M | synonyms = <small>[3-hydroxy-10,13-dimethyl-2-morpholin-4-yl-16-(1-prop-2-enyl-2,3,4,5-tetrahydropyrrol-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1''H''-cyclopenta[''a'']phenanthren-17-yl] acetate</small> }}

'''Rocuronium bromide''' (brand names '''Zemuron''', '''Esmeron'''), also referred to as "'''roc'''",<ref>{{cite journal | vauthors = Mazurek AJ, Rae B, Hann S, Ike Kirn J, Castro B, Coté CJ| title = Rocuronium versus succinylcholine: Are they equally effective during rapid-sequence induction of anesthesia? | journal = Anesthesia and Analgesia| volume = 87 |url=https://journals.lww.com/anesthesia-analgesia/abstract/1998/12000/rocuronium_versus_succinylcholine__are_they.9.aspx| issue = 6 | pages = 1259–1262 | date = December 1998 | pmid = 9842809 | pmc = | doi = 10.1213/00000539-199812000-00009| url-access = subscription }}</ref> is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia to facilitate tracheal intubation by providing skeletal muscle relaxation for surgery or mechanical ventilation. It is used for standard endotracheal intubation, as well as for rapid sequence induction. It can also be used with other drugs for medical assistance in dying.<ref>{{cite journal | vauthors = Tran DT, Newton EK, Mount VA, Lee JS, Wells GA, Perry JJ | title = Rocuronium versus succinylcholine for rapid sequence induction intubation | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 10 | article-number = CD002788 | date = October 2015 | pmid = 26512948 | pmc = 7104695 | doi = 10.1002/14651858.CD002788.pub3 }}</ref>

==Pharmacology==

=== Mechanism of action === Rocuronium bromide is a competitive antagonist for the nicotinic acetylcholine receptors at the neuromuscular junction. Of the neuromuscular-blocking drugs it is considered to be a non-depolarizing neuromuscular junction blocker, because it acts by dampening the receptor action causing muscle relaxation, instead of continual depolarisation which is the mechanism of action of the depolarizing neuromuscular junction blockers, like succinylcholine.

It was designed to be a weaker antagonist at the neuromuscular junction than pancuronium; hence its monoquaternary structure and its having an allyl group and a pyrrolidine group attached to the D ring quaternary nitrogen atom. Rocuronium has a rapid onset and intermediate duration of action.<ref name="pmid8652315">{{cite journal | vauthors = Hunter JM | title = Rocuronium: the newest aminosteroid neuromuscular blocking drug | journal = British Journal of Anaesthesia | volume = 76 | issue = 4 | pages = 481–483 | date = April 1996 | pmid = 8652315 | doi = 10.1093/bja/76.4.481 | doi-access = free }}</ref>

There is considered to be a risk of allergic reaction to the drug in some patients (particularly those with asthma), but a similar incidence of allergic reactions has been observed by using other members of the same drug class (non-depolarizing neuromuscular blocking drugs).<ref name="pmid17115010">{{cite journal | vauthors = Burburan SM, Xisto DG, Rocco PR | title = Anaesthetic management in asthma | journal = Minerva Anestesiologica | volume = 73 | issue = 6 | pages = 357–365 | date = June 2007 | pmid = 17115010 }}</ref>

The γ-cyclodextrin derivative sugammadex (trade name Bridion) is an agent to reverse the action of rocuronium by binding to it with high affinity.<ref name="pmid17312211">{{cite journal | vauthors = Naguib M | title = Sugammadex: another milestone in clinical neuromuscular pharmacology | journal = Anesthesia and Analgesia | volume = 104 | issue = 3 | pages = 575–581 | date = March 2007 | pmid = 17312211 | doi = 10.1213/01.ane.0000244594.63318.fc | doi-access = free }}</ref> Sugammadex has been in use since 2009 in many European countries; however, it was turned down for approval twice by the US FDA due to concerns over allergic reactions and bleeding,<ref>{{cite web | vauthors = McKee S |title=FDA turns down Merck & Co's sugammadex again |date=September 24, 2013 |work=PharmaTimes |url=http://www.pharmatimes.com/article/13-09-24/FDA_turns_down_Merck_Co_s_sugammadex_again.aspx |archive-url=https://web.archive.org/web/20140222043717/http://www.pharmatimes.com/article/13-09-24/FDA_turns_down_Merck_Co_s_sugammadex_again.aspx |archive-date=February 22, 2014 }}</ref> but finally approved the medication for use during surgical procedures in the United States on December 15, 2015.<ref>{{Cite web|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm477512.htm|archive-url=https://web.archive.org/web/20151215215811/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm477512.htm|archive-date=December 15, 2015|title=Press Announcements - FDA approves Bridion to reverse effects of neuromuscular blocking drugs used during surgery|website=www.fda.gov|language=en|access-date=2017-01-07}}</ref> The acetylcholinesterase inhibitor neostigmine can also be used as a reversal agent of rocuronium but is not as effective as sugammadex. Neostigmine is often still used due to its low cost compared with 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== It was introduced in 1994.

== Society and culture ==

=== Euthanasia === Since 2016, rocuronium bromide has been the standard drug, along with propofol, administered to patients for euthanasia in Canada.<ref name="divisionsbc.ca">{{cite web | work = Divisions of Family Practice | date = 2017 | location = Comox Valley, BC | url = https://divisionsbc.ca/sites/default/files/51936/Medical%20Assistance%20in%20Dying%20(MAID)%20Protocols%20and%20Procedures%20Handbook%20Comox%20Valley%202017%20-%202nd%20edition_0.pdf | title = Medical Assistance in Dying (MAiD): Protocols and Procedures Handbook. }}</ref>

=== Brand names === Rocuronium bromide is marketed under the brand name Zemuron in the United States and Esmeron in most other countries.{{cn|date=September 2024}}

== References == {{Reflist}}

{{Muscle relaxants}} {{Nicotinic acetylcholine receptor modulators}} {{Schering-Plough|state=autocollapse}} {{Portal bar | Medicine}} {{Authority control}}

Category:Muscle relaxants Category:Nicotinic antagonists Category:Quaternary ammonium compounds Category:4-Morpholinyl compounds Category:Drugs developed by Schering-Plough Category:Drugs developed by Merck & Co. Category:Pyrrolidines Category:Acetate esters Category:Chemical substances for emergency medicine Category:Allyl compounds Category:Neuromuscular blockers Category:Lethal injection components