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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Rapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.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
Salts
Name/CAS Structure Properties
Rapacuronium bromide
Thumb
  • InChI Key: LVQTUXZKLGXYIU-GWSNJHLMSA-M
  • Monoisotopic Mass: 676.381471097
  • Average Mass: 677.795
DBSALT000337
Brand names
NameCompany
RaplonNot Available
Brand mixturesNot Available
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[8.7.0.0^{2,7}.0^{11,15}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassSteroid Esters
Direct parentSteroid Esters
Alternative parentsAndrogens and Derivatives; Piperidines; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Ethers
Substituentspiperidine; tertiary amine; carboxylic acid ester; enolate; ether; carboxylic acid derivative; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the steroid esters. These are compounds containing a steroid moeity which bears a carboxylic acid ester group.
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
Property Value Probability
Human Intestinal Absorption - 0.5993
Blood Brain Barrier + 0.8937
Caco-2 permeable + 0.5
P-glycoprotein substrate Substrate 0.8064
P-glycoprotein inhibitor I Inhibitor 0.8735
P-glycoprotein inhibitor II Inhibitor 0.908
Renal organic cation transporter Non-inhibitor 0.7446
CYP450 2C9 substrate Non-substrate 0.85
CYP450 2D6 substrate Non-substrate 0.7966
CYP450 3A4 substrate Substrate 0.7018
CYP450 1A2 substrate Non-inhibitor 0.7843
CYP450 2C9 substrate Non-inhibitor 0.851
CYP450 2D6 substrate Non-inhibitor 0.8561
CYP450 2C19 substrate Non-inhibitor 0.7692
CYP450 3A4 substrate Non-inhibitor 0.6044
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7403
Ames test Non AMES toxic 0.6904
Carcinogenicity Non-carcinogens 0.8664
Biodegradation Not ready biodegradable 0.9886
Rat acute toxicity 2.6637 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8796
hERG inhibition (predictor II) Non-inhibitor 0.7349
Pharmacoeconomics
Manufacturers
  • Organon usa inc
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 g/lALOGPS
logP3.45ALOGPS
logP2.32ChemAxon
logS-7.6ALOGPS
pKa (strongest basic)9.65ChemAxon
physiological charge2ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area55.84ChemAxon
rotatable bond count9ChemAxon
refractivity183.1ChemAxon
polarizability72.29ChemAxon
number of rings6ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound5311398
PubChem Substance46506932
ChemSpider4470889
PharmGKBPA451227
RxListhttp://www.rxlist.com/cgi/generic/raplon.htm
WikipediaRapacuronium
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