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Rapacuronium bromide

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Pharmaceutical drug
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(November 2007)
Pharmaceutical compound
Rapacuronium bromide
Rapacuronium bromide
Clinical data
Other names[(2S, 3S, 5S, 8R, 9S, 10S, 13S, 14S, 16S, 17S)-3-acetyloxy-10,13-dimethyl-2-(1-piperidyl)-16-(1-prop-2-enyl-3,4,5,6-tetrahydro-2H-pyridin-1-yl)-2 ,3 ,4 ,5 ,6 ,7 ,8 ,9 ,11 ,12 ,14, 15, 16, 17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoate
Routes of
administration
Intravenous
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNot applicable
Protein bindingVariable
MetabolismHydrolyzed to active metabolites
CYP system not involved
Eliminationhalf-life141 minutes (mean)
ExcretionRenal and fecal
Identifiers
  • (2β,3α,5α,16β,17β)-3-(acetyloxy)-16-(1-allylpiperidinium-1-yl)-2-piperidin-1-yl-17-(propionyloxy)androstane bromide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.211.226Edit this at Wikidata
Chemical and physical data
FormulaC37H61N2O4+
Molar mass597.905 g·mol−1
3D model (JSmol)
  • [Br-].O=C(O[C@H]6[C@@H]([N+]1(C\C=C)CCCCC1)C[C@@H]5[C@]6(C)CC[C@H]3[C@H]5CC[C@H]4C[C@H](OC(=O)C)[C@@H](N2CCCCC2)C[C@]34C)CC
  • 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 checkY
  • Key:LVQTUXZKLGXYIU-GWSNJHLMSA-M checkY
 ☒NcheckY (what is this?)  (verify)

Rapacuronium bromide (brand nameRaplon) is a rapidly acting, non-depolarizingaminosteroidneuromuscular blocker formerly used in modernanaesthesia, to aid and enableendotracheal intubation, which is often necessary to assist in the controlled ventilation of unconscious patients during surgery and sometimes inintensive care. As a non-depolarizing agent it did not cause initial stimulation of muscles before weakening them.[1]

Due to risk of fatalbronchospasm it was withdrawn from theUnited States market byOrganon on March 27, 2001, less than 2 years after its FDA approval in 1999.[2]

References

[edit]
  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 fromthe original(PDF) on 24 September 2008.


Peripherally acting
(primarilyantinicotinic,
NMJ block)
Non-depolarizing
Curarealkaloids
4° ammonium agents
Depolarizing
ACh release inhibitors
Centrally acting
Carbamic acid esters
Benzodiazepines
Nonbenzodiazepines
Thienodiazepines
Quinazolines
Anticholinergics
(Antimuscarinics)
Other
Directly acting
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
Stub icon

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