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Rocuronium bromide

From Wikipedia, the free encyclopedia
Non-depolarizing neuromuscular blocker

Pharmaceutical compound
Rocuronium bromide
Molecular structure of rocuronium
3D representation of a rocuronium molecule
Clinical data
Trade namesEsmeron, Zemuron
Other names[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
AHFS/Drugs.comMonograph
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNA
Protein binding~30%
Metabolismsome de-acetylation
Eliminationhalf-life66–80 minutes
ExcretionUnchanged, inbile andurine
Identifiers
  • 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
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.122.235Edit this at Wikidata
Chemical and physical data
FormulaC32H53BrN2O4
Molar mass609.690 g·mol−1
3D model (JSmol)
  • 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-]
  • InChI=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 ☒N
  • Key:OYTJKRAYGYRUJK-FMCCZJBLSA-M ☒N
 ☒NcheckY (what is this?)  (verify)

Rocuronium bromide (brand namesZemuron,Esmeron), also referred to as "roc",[2] is anaminosteroidnon-depolarizingneuromuscular blocker ormuscle relaxant used in modernanaesthesia to facilitatetracheal intubation by providingskeletal muscle relaxation forsurgery ormechanical ventilation. It is used for standardendotracheal intubation, as well as forrapid sequence induction. It can also be used with other drugs formedical assistance in dying.[3]

Pharmacology

[edit]

Mechanism of action

[edit]

Rocuronium bromide is acompetitive antagonist for thenicotinic acetylcholine receptors at the neuromuscular junction. Of theneuromuscular-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, likesuccinylcholine.

It was designed to be a weaker antagonist at the neuromuscular junction thanpancuronium; hence its monoquaternary structure and its having anallyl group and a pyrrolidine group attached to the D ring quaternary nitrogen atom. Rocuronium has a rapid onset and intermediate duration of action.[4]

There is considered to be a risk of allergic reaction to the drug in some patients (particularly those withasthma), but a similar incidence of allergic reactions has been observed by using other members of the same drug class (non-depolarizing neuromuscular blocking drugs).[5]

The γ-cyclodextrin derivativesugammadex (trade name Bridion) is an agent to reverse the action of rocuronium by binding to it with high affinity.[6] 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,[7] but finally approved the medication for use during surgical procedures in the United States on December 15, 2015.[8] The acetylcholinesterase inhibitorneostigmine 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.[9]

History

[edit]

It was introduced in 1994.

Society and culture

[edit]

Euthanasia

[edit]

Since 2016, rocuronium bromide has been the standard drug, along withpropofol, administered to patients foreuthanasia in Canada.[10]

Brand names

[edit]

Rocuronium bromide is marketed under the brand name Zemuron in the United States and Esmeron in most other countries.[citation needed]

References

[edit]
  1. ^"ROCURONIUM-HAMELN (Hameln Pharma Pty Ltd) | Therapeutic Goods Administration (TGA)". Archived fromthe original on September 15, 2024. RetrievedAugust 25, 2025.
  2. ^Mazurek AJ, Rae B, Hann S, Ike Kirn J, Castro B, Coté CJ (December 1998)."Rocuronium versus succinylcholine: Are they equally effective during rapid-sequence induction of anesthesia?".Anesthesia and Analgesia.87 (6):1259–1262.doi:10.1213/00000539-199812000-00009.PMID 9842809.
  3. ^Tran DT, Newton EK, Mount VA, Lee JS, Wells GA, Perry JJ (October 2015)."Rocuronium versus succinylcholine for rapid sequence induction intubation".The Cochrane Database of Systematic Reviews.2015 (10) CD002788.doi:10.1002/14651858.CD002788.pub3.PMC 7104695.PMID 26512948.
  4. ^Hunter JM (April 1996)."Rocuronium: the newest aminosteroid neuromuscular blocking drug".British Journal of Anaesthesia.76 (4):481–483.doi:10.1093/bja/76.4.481.PMID 8652315.
  5. ^Burburan SM, Xisto DG, Rocco PR (June 2007). "Anaesthetic management in asthma".Minerva Anestesiologica.73 (6):357–365.PMID 17115010.
  6. ^Naguib M (March 2007)."Sugammadex: another milestone in clinical neuromuscular pharmacology".Anesthesia and Analgesia.104 (3):575–581.doi:10.1213/01.ane.0000244594.63318.fc.PMID 17312211.
  7. ^McKee S (September 24, 2013)."FDA turns down Merck & Co's sugammadex again".PharmaTimes. Archived fromthe original on February 22, 2014.
  8. ^"Press Announcements - FDA approves Bridion to reverse effects of neuromuscular blocking drugs used during surgery".www.fda.gov. Archived fromthe original on December 15, 2015. RetrievedJanuary 7, 2017.
  9. ^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.
  10. ^"Medical Assistance in Dying (MAiD): Protocols and Procedures Handbook"(PDF).Divisions of Family Practice. Comox Valley, BC. 2017.
Peripherally acting
(primarilyantinicotinic,
NMJ block)
Non-depolarizing
Curarealkaloids
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nAChRsTooltip Nicotinic acetylcholine receptors
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