rocuronium bromide
{{Short description|Non-depolarizing neuromuscular blocker}}
{{Use mdy dates|date=September 2024}}
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{{Drugbox
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| verifiedrevid = 391923978
| image = Rocuronium.svg
| width = 250
| alt =
| 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 = https://www.tga.gov.au/resources/prescription-medicines-registrations/rocuronium-hameln-hameln-pharma-pty-ltd
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| legal_UK = POM
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| bioavailability = NA
| protein_bound = ~30%
| metabolism = some de-acetylation
| elimination_half-life = 66–80 minutes
| excretion = Unchanged, in bile and urine
| 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 = [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-1H-cyclopenta[a]phenanthren-17-yl] acetate
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Rocuronium bromide (brand names Zemuron, Esmeron) 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 (RSI).{{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 | pages = CD002788 | date = October 2015 | pmid = 26512948 | pmc = 7104695 | doi = 10.1002/14651858.CD002788.pub3 }}
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.{{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 }}
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).{{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 }}
The γ-cyclodextrin derivative sugammadex (trade name Bridion) is an agent to reverse the action of rocuronium by binding to it with high affinity.{{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 }} 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,{{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 |url-status=dead |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 }} but finally approved the medication for use during surgical procedures in the United States on December 15, 2015.{{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|url-status=dead|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}} 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.{{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 }}
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.{{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. }}
= 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}}
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Category:Nicotinic antagonists
Category:Quaternary ammonium compounds
Category:4-Morpholinyl compounds
Category:Drugs developed by Schering-Plough
Category:Drugs developed by Merck & Co.
Category:Chemical substances for emergency medicine