Rapacuronium bromide

Rapacuronium bromide
	File:Rapacuronium bromide.svg 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Legal status	US: Withdrawn;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 check;
ChemSpider	4470889 check;
UNII	65Q4QDG4KC;
ChEMBL	ChEMBL1201352 ☒;
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 check; Key:LVQTUXZKLGXYIU-GWSNJHLMSA-M check;
	☒check (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it did not cause initial stimulation of muscles before weakening them.^[1] Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001, less than 2 years after its FDA approval in 1999.^[2]

References

↑ 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.

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[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.

[1]

[2]

Rapacuronium bromide

References

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Clinical data
File:Rapacuronium bromide.svg Rapacuronium bromide
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^☒N
PubChem CID	5311398
DrugBank	DB04834^checkY
ChemSpider	4470889^checkY
UNII	65Q4QDG4KC
ChEMBL	ChEMBL1201352^☒N
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^checkY Key:LVQTUXZKLGXYIU-GWSNJHLMSA-M^checkY
^☒NcheckY (what is this?) (verify)