Rocuronium bromide

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Rocuronium bromide
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Molecular structure of rocuronium
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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
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Legal status
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Pharmacokinetic data
BioavailabilityNA
Protein binding~30%
Metabolismsome de-acetylation
Elimination half-life66–80 minutes
ExcretionUnchanged, in bile and urine
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
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Chemical and physical data
FormulaC32H53BrN2O4
Molar mass609.690 g·mol−1
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  • 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
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Rocuronium bromide (brand names Zemuron, Esmeron), also referred to as "roc",[2] 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.[3]

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.[4]

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).[5]

The γ-cyclodextrin derivative sugammadex (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 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.[9]

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.[10]

Brand names

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

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."ROCURONIUM-HAMELN (Hameln Pharma Pty Ltd) | Therapeutic Goods Administration (TGA)". Archived from the original on September 15, 2024. Retrieved August 25, 2025.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Burburan SM, Xisto DG, Rocco PR (June 2007). "Anaesthetic management in asthma". Minerva Anestesiologica. 73 (6): 357–365. PMID 17115010.
  6. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.McKee S (September 24, 2013). "FDA turns down Merck & Co's sugammadex again". PharmaTimes. Archived from the original on February 22, 2014.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Press Announcements - FDA approves Bridion to reverse effects of neuromuscular blocking drugs used during surgery". www.fda.gov. Archived from the original on December 15, 2015. Retrieved January 7, 2017.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Medical Assistance in Dying (MAiD): Protocols and Procedures Handbook" (PDF). Divisions of Family Practice. Comox Valley, BC. 2017.

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