Rapacuronium

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Rapacuronium
Systematic (IUPAC) name
250px
(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Legal status	Withdrawn (U.S)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
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^{Script error: No such module "String".}
Molar mass	597.891 g/mol[[Script error: No such module "String".]]

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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Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001.^[1]

References

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Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
Neuromuscular junction block)

Non-depolarizing

Curare alkaloids	Alcuronium · Dimethyltubocurarine · Tubocurarine · C-Toxiferine I
Tertiary amines / Non-curare alkaloids	Dihydro-β-erythroidine · Thesine · Malouetine
Mono-, Bis- and Tris-quaternary ammonium agents	ultra-short duration: Gantacurium short duration: Mivacurium · Chandonium intermediate duration: Atracurium · Cisatracurium · Fazadinium · Rocuronium · Vecuronium · Dipyrandium · N,N'-Dimethylconessine · Stercuronium · Dacuronium · Mytolon long duration: Doxacurium · Dimethyltubocurarine · Pancuronium · Pipecuronium · Laudexium · Gallamine · Benzoquinonium · Decaethonium · Succinyl-bis-β-phenylcholine · Anatruxonium · Truxilonium · Cyclobutonium · Dipyronium · Pyrocurinum · Tercuronium · Diadonium unsorted: Hexafluronium (Hexafluorenium) · Myanesin · Cyclobutonium · Mebutanium · Amidonium · Nubitanium · Quilidium · Decadonium

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine) · Succinyl-β-phenylcholine · Suxethonium Polyalkylene derivatives: Decamethonium · Pentamethonium · Hexamethonium · Carbolonium · Dioxonium

ACh release inhibitors

Clostridium botulinum toxin · Atraxotoxin · β-Bungarotoxin · Black widow spider venom

Centrally acting

Carbamic acid esters	Carisoprodol · Febarbamate · Meprobamate · Methocarbamol · Phenprobamate · Styramate · Tybamate
Benzodiazepines	Bentazepam · Diazepam · Lorazepam · Nitrazepam · Tetrazepam
Anticholinergics (Antimuscarinics)	Cyclobenzaprine · Orphenadrine
Other	Baclofen · Chlormezanone · Chlorphenesin • Chlorzoxazone · Donepezil · Eperisone · Flopropione · Mephenesin · Mephenoxalone · Metaxalone · Phenyramidol · Pridinol · Promoxolane · Quinine · Thiocolchicoside · Tizanidine · Tolperisone · Trazadone

Directly acting

Dantrolene

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/hist

noco(m, s, c)/cong(d)/tumr, sysi/epon, injr

proc, drug (M1A/3)

Cholinergics

Receptor ligands

mAChR

Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorpheniramine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)

nAChR

Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • Xenon

Reuptake inhibitors

Plasmalemmal

CHT Inhibitors	Hemicholinium-3 (Hemicholine; HC3) • Triethylcholine

Vesicular

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

Anabolism

ChAT inhibitors	1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate

Catabolism

AChE inhibitors

Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)

BChE inhibitors

* Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • Pirisudanol
Cofactors	Acetic acid • Acetylcarnitine • Acetyl-coA • Vitamin B₅ (Pantethine, Pantetheine, Panthenol)
Others	Acetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • Pralidoxime

fr:Rapacuronium

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

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Rapacuronium

References

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