Rapacuronium

Rapacuronium

Rapacuronium bromide
Systematic (IUPAC) name
(2β,3α,5α,16β,17β)-3-(acetyloxy)-16-(1-allylpiperidinium-1-yl)-2-piperidin-1-yl-17-(propionyloxy)androstane bromide
Clinical data
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Intravenous
Legal status
Legal status	Withdrawn (U.S)
Pharmacokinetic data
Bioavailability	Not applicable
Protein binding	Variable
Metabolism	Hydrolyzed to active metabolites CYP system not involved
Biological half-life	141 minutes (mean)
Excretion	Renal and fecal
Identifiers
CAS Number	156137-99-4
ATC code	none
PubChem	CID 5311398
DrugBank	DB04834
ChemSpider	4470889
ChEMBL	CHEMBL1201352
Synonyms	[(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
Chemical data
Formula	C37H61N2O4^+
Molar mass	597.891 g/mol
SMILES [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 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
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Rapacuronium (Raplon) is a rapidly acting, non-depolarizing 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Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001, less than 2 years after its FDA approval in 1999.^[1]

References

1. Shapse, Deborah (March 27, 2001). Voluntary Market Withdrawal PDF (10.8 KiB). Organon International. Retrieved on 2007-04-02.