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Identification
NameRapacuronium
Accession NumberDB04834
TypeSmall Molecule
GroupsWithdrawn
DescriptionRapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
RaplonNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Rapacuronium bromide
156137-99-4
Thumb
  • InChI Key: LVQTUXZKLGXYIU-GWSNJHLMSA-M
  • Monoisotopic Mass: 676.381471097
  • Average Mass: 677.795
DBSALT000337
Categories
UNIIGG1LBM463S
CAS number465499-11-0
WeightAverage: 597.904
Monoisotopic: 597.462584872
Chemical FormulaC37H61N2O4
InChI KeyHTIKWNNIPGXLGM-YLINKJIISA-N
InChI
InChI=1S/C37H61N2O4/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/q+1/t27-,28+,29-,30-,31-,32-,33-,35-,36-,37-/m0/s1
IUPAC Name
1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)-14-(propanoyloxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]-1-(prop-2-en-1-yl)piperidin-1-ium
SMILES
[H][C@@]12C[C@@H]([[email protected]](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[[email protected]](OC(C)=O)[[email protected]](C[C@]12C)N1CCCCC1)[N+]1(CC=C)CCCCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Acetate salt
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in anaesthesia, to aid and enable endotracheal intubation.
PharmacodynamicsRapacuronium is a rapidly acting, non-depolarizing neuromuscular blocker.
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingVariable. Plasma protein binding of rapacuronium was studied in vitro for human plasma by equilibrium dialysis. The protein binding was variable and ranged between 50% and 88%, which was at least partly due to hydrolysis of rapacuronium bromide to its 3-hydroxy metabolite. The specific plasma protein to which rapacuronium binds is unknown. Plasma protein binding of the 3-hydroxy metabolite was not determined.
Metabolism

Hydrolyzed to active metabolites (Cytochrome P450 system is not involved).

Route of eliminationNot Available
Half life141 minutes (mean)
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5993
Blood Brain Barrier+0.8937
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.8064
P-glycoprotein inhibitor IInhibitor0.8735
P-glycoprotein inhibitor IIInhibitor0.908
Renal organic cation transporterNon-inhibitor0.7446
CYP450 2C9 substrateNon-substrate0.85
CYP450 2D6 substrateNon-substrate0.7966
CYP450 3A4 substrateSubstrate0.7018
CYP450 1A2 substrateNon-inhibitor0.7843
CYP450 2C9 inhibitorNon-inhibitor0.851
CYP450 2D6 inhibitorNon-inhibitor0.8561
CYP450 2C19 inhibitorNon-inhibitor0.7692
CYP450 3A4 inhibitorNon-inhibitor0.6044
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7403
Ames testNon AMES toxic0.6904
CarcinogenicityNon-carcinogens0.8664
BiodegradationNot ready biodegradable0.9886
Rat acute toxicity2.6637 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8796
hERG inhibition (predictor II)Non-inhibitor0.7349
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5418226 No1993-04-142013-04-14Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.64e-06 mg/mLALOGPS
logP3.79ALOGPS
logP2.32ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)9.65ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity183.1 m3·mol-1ChemAxon
Polarizability72.25 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
1,10-Phenanthroline1,10-Phenanthroline may decrease the neuromuscular blocking activities of Rapacuronium.
4-AndrostenedioneRapacuronium may increase the adverse neuromuscular activities of 4-Androstenedione.
AlclometasoneRapacuronium may increase the adverse neuromuscular activities of Alclometasone.
AldosteroneRapacuronium may increase the adverse neuromuscular activities of Aldosterone.
AmbenoniumAmbenonium may decrease the neuromuscular blocking activities of Rapacuronium.
AmcinonideRapacuronium may increase the adverse neuromuscular activities of Amcinonide.
AmlodipineAmlodipine may increase the neuromuscular blocking activities of Rapacuronium.
AmrinoneAmrinone may increase the neuromuscular blocking activities of Rapacuronium.
AzelnidipineAzelnidipine may increase the neuromuscular blocking activities of Rapacuronium.
AzimilideAzimilide may increase the neuromuscular blocking activities of Rapacuronium.
BarnidipineBarnidipine may increase the neuromuscular blocking activities of Rapacuronium.
Beclomethasone dipropionateRapacuronium may increase the adverse neuromuscular activities of Beclomethasone dipropionate.
BenidipineBenidipine may increase the neuromuscular blocking activities of Rapacuronium.
BepridilBepridil may increase the neuromuscular blocking activities of Rapacuronium.
BetamethasoneRapacuronium may increase the adverse neuromuscular activities of Betamethasone.
BudesonideRapacuronium may increase the adverse neuromuscular activities of Budesonide.
CiclesonideRapacuronium may increase the adverse neuromuscular activities of Ciclesonide.
CilnidipineCilnidipine may increase the neuromuscular blocking activities of Rapacuronium.
CinnarizineCinnarizine may increase the neuromuscular blocking activities of Rapacuronium.
ClevidipineClevidipine may increase the neuromuscular blocking activities of Rapacuronium.
Clobetasol propionateRapacuronium may increase the adverse neuromuscular activities of Clobetasol propionate.
ClocortoloneRapacuronium may increase the adverse neuromuscular activities of Clocortolone.
Cortisone acetateRapacuronium may increase the adverse neuromuscular activities of Cortisone acetate.
CoumaphosCoumaphos may decrease the neuromuscular blocking activities of Rapacuronium.
DarodipineDarodipine may increase the neuromuscular blocking activities of Rapacuronium.
DecamethoniumDecamethonium may decrease the neuromuscular blocking activities of Rapacuronium.
DehydroepiandrosteroneRapacuronium may increase the adverse neuromuscular activities of Dehydroepiandrosterone.
dehydroepiandrosterone sulfateRapacuronium may increase the adverse neuromuscular activities of dehydroepiandrosterone sulfate.
DemecariumDemecarium may decrease the neuromuscular blocking activities of Rapacuronium.
DesfluraneDesflurane may increase the neuromuscular blocking activities of Rapacuronium.
DesoximetasoneRapacuronium may increase the adverse neuromuscular activities of Desoximetasone.
Desoxycorticosterone acetateRapacuronium may increase the adverse neuromuscular activities of Desoxycorticosterone acetate.
DexamethasoneRapacuronium may increase the adverse neuromuscular activities of Dexamethasone.
Dexamethasone isonicotinateRapacuronium may increase the adverse neuromuscular activities of Dexamethasone isonicotinate.
DichlorvosDichlorvos may decrease the neuromuscular blocking activities of Rapacuronium.
DiflorasoneRapacuronium may increase the adverse neuromuscular activities of Diflorasone.
DifluocortoloneRapacuronium may increase the adverse neuromuscular activities of Difluocortolone.
DifluprednateRapacuronium may increase the adverse neuromuscular activities of Difluprednate.
DiltiazemDiltiazem may increase the neuromuscular blocking activities of Rapacuronium.
DonepezilDonepezil may decrease the neuromuscular blocking activities of Rapacuronium.
DotarizineDotarizine may increase the neuromuscular blocking activities of Rapacuronium.
EchothiophateEchothiophate may decrease the neuromuscular blocking activities of Rapacuronium.
EdrophoniumEdrophonium may decrease the neuromuscular blocking activities of Rapacuronium.
EfonidipineEfonidipine may increase the neuromuscular blocking activities of Rapacuronium.
EnfluraneEnflurane may increase the neuromuscular blocking activities of Rapacuronium.
EperisoneEperisone may increase the neuromuscular blocking activities of Rapacuronium.
EquileninRapacuronium may increase the adverse neuromuscular activities of Equilenin.
EquilinRapacuronium may increase the adverse neuromuscular activities of Equilin.
EstroneRapacuronium may increase the adverse neuromuscular activities of Estrone.
FelodipineFelodipine may increase the neuromuscular blocking activities of Rapacuronium.
FendilineFendiline may increase the neuromuscular blocking activities of Rapacuronium.
FenthionFenthion may decrease the neuromuscular blocking activities of Rapacuronium.
FludrocortisoneRapacuronium may increase the adverse neuromuscular activities of Fludrocortisone.
FlumethasoneRapacuronium may increase the adverse neuromuscular activities of Flumethasone.
FlunarizineFlunarizine may increase the neuromuscular blocking activities of Rapacuronium.
FlunisolideRapacuronium may increase the adverse neuromuscular activities of Flunisolide.
Fluocinolone AcetonideRapacuronium may increase the adverse neuromuscular activities of Fluocinolone Acetonide.
FluocinonideRapacuronium may increase the adverse neuromuscular activities of Fluocinonide.
FluocortoloneRapacuronium may increase the adverse neuromuscular activities of Fluocortolone.
FluorometholoneRapacuronium may increase the adverse neuromuscular activities of Fluorometholone.
FluprednideneRapacuronium may increase the adverse neuromuscular activities of Fluprednidene.
FluprednisoloneRapacuronium may increase the adverse neuromuscular activities of Fluprednisolone.
FlurandrenolideRapacuronium may increase the adverse neuromuscular activities of Flurandrenolide.
Fluticasone furoateRapacuronium may increase the adverse neuromuscular activities of Fluticasone furoate.
Fluticasone PropionateRapacuronium may increase the adverse neuromuscular activities of Fluticasone Propionate.
FosphenytoinFosphenytoin may decrease the neuromuscular blocking activities of Rapacuronium.
GabapentinGabapentin may increase the neuromuscular blocking activities of Rapacuronium.
GalantamineGalantamine may decrease the neuromuscular blocking activities of Rapacuronium.
Gallamine TriethiodideGallamine Triethiodide may decrease the neuromuscular blocking activities of Rapacuronium.
Ginkgo bilobaGinkgo biloba may decrease the neuromuscular blocking activities of Rapacuronium.
HalothaneHalothane may increase the neuromuscular blocking activities of Rapacuronium.
Huperzine AHuperzine A may decrease the neuromuscular blocking activities of Rapacuronium.
HydrocortisoneRapacuronium may increase the adverse neuromuscular activities of Hydrocortisone.
IsofluraneIsoflurane may increase the neuromuscular blocking activities of Rapacuronium.
IsoflurophateIsoflurophate may decrease the neuromuscular blocking activities of Rapacuronium.
IsradipineIsradipine may increase the neuromuscular blocking activities of Rapacuronium.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Rapacuronium.
LacidipineLacidipine may increase the neuromuscular blocking activities of Rapacuronium.
LamotrigineLamotrigine may increase the neuromuscular blocking activities of Rapacuronium.
LercanidipineLercanidipine may increase the neuromuscular blocking activities of Rapacuronium.
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Rapacuronium.
MalathionMalathion may decrease the neuromuscular blocking activities of Rapacuronium.
ManidipineManidipine may increase the neuromuscular blocking activities of Rapacuronium.
MedrysoneRapacuronium may increase the adverse neuromuscular activities of Medrysone.
MefloquineMefloquine may decrease the neuromuscular blocking activities of Rapacuronium.
MelengestrolRapacuronium may increase the adverse neuromuscular activities of Melengestrol.
MemantineMemantine may decrease the neuromuscular blocking activities of Rapacuronium.
MethoxyfluraneMethoxyflurane may increase the neuromuscular blocking activities of Rapacuronium.
MethylprednisoloneRapacuronium may increase the adverse neuromuscular activities of Methylprednisolone.
MibefradilMibefradil may increase the neuromuscular blocking activities of Rapacuronium.
MinaprineMinaprine may decrease the neuromuscular blocking activities of Rapacuronium.
MometasoneRapacuronium may increase the adverse neuromuscular activities of Mometasone.
NeostigmineNeostigmine may decrease the neuromuscular blocking activities of Rapacuronium.
NicardipineNicardipine may increase the neuromuscular blocking activities of Rapacuronium.
NifedipineNifedipine may increase the neuromuscular blocking activities of Rapacuronium.
NiguldipineNiguldipine may increase the neuromuscular blocking activities of Rapacuronium.
NiludipineNiludipine may increase the neuromuscular blocking activities of Rapacuronium.
NilvadipineNilvadipine may increase the neuromuscular blocking activities of Rapacuronium.
NimesulideNimesulide may increase the neuromuscular blocking activities of Rapacuronium.
NimodipineNimodipine may increase the neuromuscular blocking activities of Rapacuronium.
NisoldipineNisoldipine may increase the neuromuscular blocking activities of Rapacuronium.
NitrendipineNitrendipine may increase the neuromuscular blocking activities of Rapacuronium.
Nitrous oxideNitrous oxide may increase the neuromuscular blocking activities of Rapacuronium.
ParamethasoneRapacuronium may increase the adverse neuromuscular activities of Paramethasone.
PerhexilinePerhexiline may increase the neuromuscular blocking activities of Rapacuronium.
PhenytoinPhenytoin may decrease the neuromuscular blocking activities of Rapacuronium.
PhysostigminePhysostigmine may decrease the neuromuscular blocking activities of Rapacuronium.
PinaveriumPinaverium may increase the neuromuscular blocking activities of Rapacuronium.
PrednicarbateRapacuronium may increase the adverse neuromuscular activities of Prednicarbate.
PrednisoloneRapacuronium may increase the adverse neuromuscular activities of Prednisolone.
PrednisoneRapacuronium may increase the adverse neuromuscular activities of Prednisone.
PregabalinPregabalin may increase the neuromuscular blocking activities of Rapacuronium.
PregnenoloneRapacuronium may increase the adverse neuromuscular activities of Pregnenolone.
PrenylaminePrenylamine may increase the neuromuscular blocking activities of Rapacuronium.
PyridostigminePyridostigmine may decrease the neuromuscular blocking activities of Rapacuronium.
RimexoloneRapacuronium may increase the adverse neuromuscular activities of Rimexolone.
RisedronateRisedronate may increase the neuromuscular blocking activities of Rapacuronium.
RivastigmineRivastigmine may decrease the neuromuscular blocking activities of Rapacuronium.
SevofluraneSevoflurane may increase the neuromuscular blocking activities of Rapacuronium.
SpironolactoneSpironolactone may increase the neuromuscular blocking activities of Rapacuronium.
TacrineTacrine may decrease the neuromuscular blocking activities of Rapacuronium.
TixocortolRapacuronium may increase the adverse neuromuscular activities of Tixocortol.
Tolfenamic AcidTolfenamic Acid may increase the neuromuscular blocking activities of Rapacuronium.
TranilastTranilast may increase the neuromuscular blocking activities of Rapacuronium.
TriamcinoloneRapacuronium may increase the adverse neuromuscular activities of Triamcinolone.
TrichlorfonTrichlorfon may decrease the neuromuscular blocking activities of Rapacuronium.
TubocurarineTubocurarine may decrease the neuromuscular blocking activities of Rapacuronium.
VerapamilVerapamil may increase the neuromuscular blocking activities of Rapacuronium.
XylometazolineXylometazoline may increase the neuromuscular blocking activities of Rapacuronium.
ZiconotideZiconotide may increase the neuromuscular blocking activities of Rapacuronium.
Food InteractionsNot Available
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Drug created on September 11, 2007 15:43 / Updated on August 17, 2016 12:24