Rocuronium bromide

Rocuronium bromide

Clinical data
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
AHFS/Drugs.com	Monograph
Routes of administration	Intravenous
ATC code	M03AC09 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	NA
Protein binding	~30%
Metabolism	some de-acetylation
Biological half-life	66–80 minutes
Excretion	Unchanged, in bile and urine
Identifiers
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
CAS Number	119302-91-9 Y
PubChem CID	441351
IUPHAR/BPS	4003
DrugBank	DB00728 N
ChemSpider	390104 N
UNII	I65MW4OFHZ
ChEMBL	CHEMBL1201244 N
Chemical and physical data
Formula	C32H53BrN2O4
Molar mass	609.678 g/mol
3D model (JSmol)	Interactive image
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-]
InChI 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
NY (what is this?)

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, most commonly required for surgery or mechanical ventilation. It is used for both standard endotracheal intubation and rapid sequence induction (RSI), although suxamethonium chloride is usually selected for RSI given its fast onset of action compared with rocuronium.

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.

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).

The γ-cyclodextrin derivative sugammadex (trade name Bridion) has been recently introduced as a novel agent to reverse the action of rocuronium.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.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.