Rocuronium bromide

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Rocuronium bromide
Rocuronium structure.png
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
Routes Intravenous
Pharmacokinetic data
Bioavailability NA
Protein binding ~30%
Metabolism some de-acetylation
Half-life 66–80 minutes
Excretion Unchanged, in bile and urine
Identifiers
CAS number 119302-91-9 YesY
ATC code M03AC09
PubChem CID 441290
IUPHAR ligand 4003
DrugBank DB00728
UNII I65MW4OFHZ N
ChEMBL CHEMBL1201244 N
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+
Mol. mass 529.774 g/mol
 N (what is this?)  (verify)

Rocuronium (Zemuron, Esmeron) is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Development[edit]

It was designed to be a weaker antagonist at the neuromuscular junction than pancuronium; hence its monoquaternary structure and its having an allyyl group and a pyrrolidine group attached to the D ring quaternary nitrogen atom. Introduced in 1994, rocuronium has rapid onset, and intermediate duration of action.[1] It 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).[2]

The γ-cyclodextrin derivative sugammadex (trade name Bridion) has been recently introduced as a novel agent to reverse the action of rocuronium. [3] Sugammadex has been in use since 2009 in many European countries, however it has been turned down for approval twice by the US FDA and is currently unavailable for use in the US due to concerns over allergic reactions and bleeding. [4]

On July 27, 2012, the State of Virginia replaced pancuronium bromide, one of the three drugs used in execution by lethal injection, with this drug.

References[edit]

  1. ^ 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. 
  2. ^ Burburan SM, Xisto DG, Rocco PR (June 2007). "Anaesthetic management in asthma". Minerva Anestesiologica 73 (6): 357–65. PMID 17115010. 
  3. ^ 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. 
  4. ^ McKee, Selina (September 24, 2013). "FDA turns down Merck & Co's sugammadex again". PharmaTimes.