Rapacuronium bromide

{{Short description|Pharmaceutical drug}}

{{Onesource|date=November 2007}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464380213

| IUPAC_name = (2β,3α,5α,16β,17β)-3-(acetyloxy)-16-(1-allylpiperidinium-1-yl)-2-piperidin-1-yl-17-(propionyloxy)androstane bromide

| image = Rapacuronium bromide.svg

| width = 250

| caption = Rapacuronium bromide

| tradename =

| pregnancy_AU =

| pregnancy_US = C

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US_comment = Withdrawn

| routes_of_administration = Intravenous

| bioavailability = Not applicable

| protein_bound = Variable

| metabolism = Hydrolyzed to active metabolites
CYP system not involved

| elimination_half-life = 141 minutes (mean)

| excretion = Renal and fecal

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 156137-99-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 65Q4QDG4KC

| ATC_prefix = none

| ATC_suffix =

| PubChem = 5311398

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB04834

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4470889

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201352

| C=37 | H=61 | N=2 | O=4| charge = +

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LVQTUXZKLGXYIU-GWSNJHLMSA-M

| 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

}}

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.{{cite journal | vauthors = Onrust SV, Foster RH | title = Rapacuronium bromide: a review of its use in anaesthetic practice | journal = Drugs | volume = 58 | issue = 5 | pages = 887–918 | date = November 1999 | pmid = 10595867 | doi = 10.2165/00003495-199958050-00011 | s2cid = 46984904 }}

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.{{cite web | vauthors = Shapse D | collaboration = Organon International | date = 27 March 2001 | url= https://www.fda.gov/medwatch/SAFETY/2001/raplon_DDR.pdf | archive-url = https://web.archive.org/web/20080924170851/https://www.fda.gov/medwatch/SAFETY/2001/raplon_DDR.pdf | archive-date = 24 September 2008 | title = Voluntary Market Withdrawal | publisher = Food and Drug Administration }}