Rocuronium bromide

Rocuronium bromide

Systematic (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
Clinical data
AHFS/Drugs.com	monograph
Legal status	UK: POM (Prescription only)
Routes of administration	Intravenous
Pharmacokinetic data
Bioavailability	NA
Protein binding	~30%
Metabolism	some de-acetylation
Biological half-life	66–80 minutes
Excretion	Unchanged, in bile and urine
Identifiers
CAS Number	119302-91-9
ATC code	M03AC09
PubChem	CID 441290
IUPHAR/BPS	4003
DrugBank	DB00728
UNII	I65MW4OFHZ
ChEMBL	CHEMBL1201244
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
Chemical data
Formula	C32H53N2O4^+
Molar mass	529.774 g/mol
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Rocuronium (Zemuron, Esmeron) is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia to facilitate endotracheal intubation by providing skeletal muscle relaxation, most commonly required for surgery or mechanical ventilation. It is used for both standard and rapid sequence induction (RSI), although Suxamethonium chloride is usually selected for RSI given its shorter duration of action compared to rocuronium.^[1]

Development

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.^[2] It was introduced in 1994, and is marketed under the trade name of Zemuron in the United States and Esmeron in most other countries.

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).^[3]

The γ-cyclodextrin derivative sugammadex (trade name Bridion) has been recently introduced as a novel agent to reverse the action of rocuronium.^[4] 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,^[5] but finally approved the medication for use in the United States on December 15, 2015.^[6]

On July 27, 2012, the U.S. state of Virginia replaced pancuronium bromide, one of the three drugs used in execution by lethal injection, with rocuronium.

It is colloquially referred to as "the rock."^[7]

References

1. Tran, DT; Newton, EK; Mount, VA; Lee, JS; Wells, GA; Perry, JJ (29 October 2015). "Rocuronium versus succinylcholine for rapid sequence induction intubation.". The Cochrane database of systematic reviews 10: CD002788. PMID 26512948.
2. Hunter JM (April 1996). "Rocuronium: the newest aminosteroid neuromuscular blocking drug". British Journal of Anaesthesia 76 (4): 481–3. doi:10.1093/bja/76.4.481. PMID 8652315.
3. Burburan SM, Xisto DG, Rocco PR (June 2007). "Anaesthetic management in asthma". Minerva Anestesiologica 73 (6): 357–65. PMID 17115010.
4. Naguib M (March 2007). "Sugammadex: another milestone in clinical neuromuscular pharmacology". Anesthesia and Analgesia 104 (3): 575–81. doi:10.1213/01.ane.0000244594.63318.fc. PMID 17312211.
5. McKee, Selina (September 24, 2013). "FDA turns down Merck & Co's sugammadex again". PharmaTimes.
6. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm477512.htm
7. Hemon, Aleksandar (June 13, 2011). "The Aquarium". The New Yorker.