Rocuronium bromide

Overview

Rocuronium bromide (brand names Zemuron, Esmeron), also referred to as "roc", 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.[1][2] WP

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. WP

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.[3] WP

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).[4] WP

The γ-cyclodextrin derivative sugammadex (trade name Bridion) is an agent to reverse the action of rocuronium by binding to it with high affinity. 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, but finally approved the medication for use during surgical procedures in the United States on December 15, 2015. 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.[5–8] WP

History

History

It was introduced in 1994. WP

Legal status

Euthanasia

Since 2016, rocuronium bromide has been the standard drug, along with propofol, administered to patients for euthanasia in Canada.[9] WP

Brand names

Rocuronium bromide is marketed under the brand name Zemuron in the United States and Esmeron in most other countries. WP⚠ Wikipedia itself has flagged this text: citation needed.

Chemistry

Formula

C32H53BrN2O4 PC

CAS number

119302-91-9 PC

Molar mass (g/mol)

609.7 PC

IUPAC name (computed by PubChem)

[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-hydroxy-10,13-dimethyl-2-morpholin-4-yl-16-(1-prop-2-enylpyrrolidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate bromide PC

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-] PC

InChIKey

OYTJKRAYGYRUJK-FMCCZJBLSA-M PC

PubChem CID

441351

IUPAC name

1-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetoxy-3-hydroxy-10,13-dimethyl-2-morpholinohexadecahydro-1H-cyclopenta WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Mazurek AJ, Rae B, Hann S, Ike Kirn J, Castro B, Coté CJ. Rocuronium versus succinylcholine: Are they equally effective during rapid-sequence induction of anesthesia?. Anesthesia and Analgesia. December 1998. doi:10.1213/00000539-199812000-00009 · PMID 9842809
2. Journal / agency Tran DT, Newton EK, Mount VA, Lee JS, Wells GA, Perry JJ. Rocuronium versus succinylcholine for rapid sequence induction intubation. The Cochrane Database of Systematic Reviews. October 2015. doi:10.1002/14651858.CD002788.pub3 · PMID 26512948 · PMC7104695
3. Journal / agency Hunter JM. Rocuronium: the newest aminosteroid neuromuscular blocking drug. British Journal of Anaesthesia. April 1996. doi:10.1093/bja/76.4.481 · PMID 8652315
4. Journal / agency Burburan SM, Xisto DG, Rocco PR. Anaesthetic management in asthma. Minerva Anestesiologica. June 2007. PMID 17115010
5. Journal / agency Naguib M. Sugammadex: another milestone in clinical neuromuscular pharmacology. Anesthesia and Analgesia. March 2007. doi:10.1213/01.ane.0000244594.63318.fc · PMID 17312211
6. Other McKee S. FDA turns down Merck & Co's sugammadex again. September 24, 2013
7. Journal / agency Press Announcements - FDA approves Bridion to reverse effects of neuromuscular blocking drugs used during surgery
8. Journal / agency Carron M, Zarantonello F, Tellaroli P, Ori C. Efficacy and safety of sugammadex compared to neostigmine for reversal of neuromuscular blockade: a meta-analysis of randomized controlled trials. Journal of Clinical Anesthesia. December 2016. doi:10.1016/j.jclinane.2016.06.018 · PMID 27871504
9. Other Medical Assistance in Dying (MAiD): Protocols and Procedures Handbook. 2017

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.