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Rapacuronium bromide

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Pharmaceutical compound
Rapacuronium bromide
Rapacuronium bromide
Clinical data
Other namesphenanthren-17-yl]propanoate
Routes of
administration		Intravenous
ATC code
  • none
Legal status
Legal status
  • US: Withdrawn
Pharmacokinetic data
BioavailabilityNot applicable
Protein bindingVariable
MetabolismHydrolyzed to active metabolites
CYP system not involved
Elimination half-life141 minutes (mean)
ExcretionRenal and fecal
Identifiers
IUPAC name
  • (2β,3α,5α,16β,17β)-3-(acetyloxy)-16-(1-allylpiperidinium-1-yl)-2-piperidin-1-yl-17-(propionyloxy)androstane bromide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.211.226 Edit this at Wikidata
Chemical and physical data
FormulaC37H61N2O4
Molar mass597.905 g·mol
3D model (JSmol)
SMILES
  • .O=C(O6(1(C\C=C)CCCCC1)C56(C)CC35CC4C(OC(=O)C)(N2CCCCC2)C34C)CC
InChI
  • InChI=1S/C37H61N2O4.BrH/c1-6-20-39(21-12-9-13-22-39)32-24-30-28-15-14-27-23-33(42-26(3)40)31(38-18-10-8-11-19-38)25-37(27,5)29(28)16-17-36(30,4)35(32)43-34(41)7-2;/h6,27-33,35H,1,7-25H2,2-5H3;1H/q+1;/p-1/t27-,28+,29-,30-,31-,32-,33-,35-,36-,37-;/m0./s1
  • Key:LVQTUXZKLGXYIU-GWSNJHLMSA-M
  (what is this?)  (verify)

Rapacuronium bromide (brand name Raplon) is a rapidly acting, non-depolarizing aminosteroid neuromuscular blocker formerly used in modern anaesthesia, to aid and enable endotracheal intubation, which is often necessary to assist in the controlled ventilation of unconscious patients during surgery and sometimes in intensive care. As a non-depolarizing agent it did not cause initial stimulation of muscles before weakening them.

Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001, less than 2 years after its FDA approval in 1999.

References

  1. Onrust SV, Foster RH (November 1999). "Rapacuronium bromide: a review of its use in anaesthetic practice". Drugs. 58 (5): 887–918. doi:10.2165/00003495-199958050-00011. PMID 10595867. S2CID 46984904.
  2. Shapse D, et al. (Organon International) (27 March 2001). "Voluntary Market Withdrawal" (PDF). Food and Drug Administration. Archived from the original (PDF) on 24 September 2008.


Skeletal muscle relaxants (M03)
Peripherally acting
(primarily antinicotinic,
NMJ block)
Non-depolarizing
Curare alkaloids
4° ammonium agents
Depolarizing
ACh release inhibitors
Centrally acting
Carbamic acid esters
Benzodiazepines
Nonbenzodiazepines
Thienodiazepines
Quinazolines
Anticholinergics
(Antimuscarinics)
Other
Directly acting
Nicotinic acetylcholine receptor modulators
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(and PAMsTooltip positive allosteric modulators)
Antagonists
(and NAMsTooltip negative allosteric modulators)
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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