Rapacuronium bromide

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Legal status	US: Withdrawn;
Pharmacokinetic data
Bioavailability	Not applicable
Protein binding	Variable
Metabolism	Hydrolyzed to active metabolites; CYP system not involved
Elimination half-life	141 minutes (mean)
Excretion	Renal 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	156137-99-4 ;
PubChem CID	5311398;
DrugBank	DB04834 ;
ChemSpider	4470889 ;
UNII	65Q4QDG4KC;
ChEMBL	ChEMBL1201352 ;
CompTox Dashboard (EPA)	DTXSID7048823 ;
ECHA InfoCard	100.211.226
Chemical and physical data
Formula	C37H61N2O4+
Molar mass	597.905 g·mol−1
3D model (JSmol)	Interactive image;
	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 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.^[1]

Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001, less than 2 years after its FDA approval in 1999.^[2]

^ 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.
^ 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.

[Onrust_1999-1] 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.

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