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Rocuronium bromide

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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
Legal status
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 Registry Number  Y
ATC code M03
PubChem CID:
IUPHAR/BPS
DrugBank  N
UNII  N
ChEMBL  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+
Molecular mass 529.774 g/mol
 N   

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

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 rapid onset, and intermediate duration of action.[1] 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).[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 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."[5]

References

  1. ^ Hunter JM (April 1996). "Rocuronium: the newest aminosteroid neuromuscular blocking drug". British Journal of Anaesthesia 76 (4): 481–3.  
  2. ^ Burburan SM, Xisto DG, Rocco PR (June 2007). "Anaesthetic management in asthma". Minerva Anestesiologica 73 (6): 357–65.  
  3. ^ Naguib M (March 2007). "Sugammadex: another milestone in clinical neuromuscular pharmacology". Anesthesia and Analgesia 104 (3): 575–81.  
  4. ^ McKee, Selina (September 24, 2013). "FDA turns down Merck & Co's sugammadex again". PharmaTimes. 
  5. ^ Hemon, Aleksandar (June 13, 2011). "The Aquarium". The New Yorker. 
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