Rocuronium bromide

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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.commonograph
Pregnancy cat. ?
Legal statusPOM (UK)
RoutesIntravenous
Pharmacokinetic data
BioavailabilityNA
Protein binding~30%
Metabolismsome de-acetylation
Half-life66–80 minutes
ExcretionUnchanged, in bile and urine
Identifiers
CAS number119302-91-9 YesY
ATC codeM03AC09
PubChemCID 441290
IUPHAR ligand4003
DrugBankDB00728
UNIII65MW4OFHZ N
ChEMBLCHEMBL1201244 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
FormulaC32H53N2O4+
Mol. mass529.774 g/mol
 N (what is this?)  (verify)
 
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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.commonograph
Pregnancy cat. ?
Legal statusPOM (UK)
RoutesIntravenous
Pharmacokinetic data
BioavailabilityNA
Protein binding~30%
Metabolismsome de-acetylation
Half-life66–80 minutes
ExcretionUnchanged, in bile and urine
Identifiers
CAS number119302-91-9 YesY
ATC codeM03AC09
PubChemCID 441290
IUPHAR ligand4003
DrugBankDB00728
UNIII65MW4OFHZ N
ChEMBLCHEMBL1201244 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
FormulaC32H53N2O4+
Mol. mass529.774 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.

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]

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

  1. ^ Hunter JM (April 1996). "Rocuronium: the newest aminosteroid neuromuscular blocking drug". British Journal of Anaesthesia 76 (4): 481–3. PMID 8652315. http://bja.oxfordjournals.org/cgi/pmidlookup?view=long&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. http://www.anesthesia-analgesia.org/cgi/pmidlookup?view=long&pmid=17312211.