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Identification
NameRapacuronium
Accession NumberDB04834
TypeSmall Molecule
GroupsWithdrawn
Description

Rapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
RaplonNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Rapacuronium bromide
Thumb
  • InChI Key: LVQTUXZKLGXYIU-GWSNJHLMSA-M
  • Monoisotopic Mass: 676.381471097
  • Average Mass: 677.795
DBSALT000337
CategoriesNot Available
CAS number156137-99-4
WeightAverage: 677.795
Monoisotopic: 676.381471097
Chemical FormulaC37H61BrN2O4
InChI KeyLVQTUXZKLGXYIU-GWSNJHLMSA-M
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
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 bromide
SMILES
[Br-].[H][C@@]12C[C@@H]([C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](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
  • Cyclohexylamine
  • Piperidine
  • Acetate salt
  • Quaternary ammonium salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • 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
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 substrateNon-inhibitor0.851
CYP450 2D6 substrateNon-inhibitor0.8561
CYP450 2C19 substrateNon-inhibitor0.7692
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
CountryPatent NumberApprovedExpires (estimated)
United States54182261993-04-142013-04-14
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.82e-05 mg/mLALOGPS
logP3.45ALOGPS
logP2.32ChemAxon
logS-7.6ALOGPS
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
Polarizability72.29 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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on September 11, 2007 15:43 / Updated on September 16, 2013 17:25