Rapacuronium

Identification

Name
Rapacuronium
Accession Number
DB04834
Type
Small Molecule
Groups
Withdrawn
Description

Rapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Rapacuronium bromide65Q4QDG4KC156137-99-4LVQTUXZKLGXYIU-GWSNJHLMSA-M
International/Other Brands
Raplon
Categories
UNII
GG1LBM463S
CAS number
465499-11-0
Weight
Average: 597.904
Monoisotopic: 597.462584872
Chemical Formula
C37H61N2O4
InChI Key
HTIKWNNIPGXLGM-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]([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

Pharmacology

Indication

Used in anaesthesia, to aid and enable endotracheal intubation.

Pharmacodynamics

Rapacuronium is a rapidly acting, non-depolarizing neuromuscular blocker.

Mechanism of action
TargetActionsOrganism
AMuscarinic acetylcholine receptor M2
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

Variable. 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 elimination
Not Available
Half life

141 minutes (mean)

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5311399
PubChem Substance
46506932
ChemSpider
4470890
ChEBI
135845
ChEMBL
CHEMBL1201352
PharmGKB
PA451227
RxList
RxList Drug Page
Wikipedia
Rapacuronium

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5418226No1993-04-142013-04-14Us

Properties

State
Solid
Experimental Properties
Not 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androstane steroids / Piperidines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts
show 4 more
Substituents
Steroid ester / Androstane-skeleton / Dicarboxylic acid or derivatives / Piperidine / Quaternary ammonium salt / Tetraalkylammonium salt / Amino acid or derivatives / Carboxylic acid ester / Tertiary amine / Tertiary aliphatic amine
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Jooste E, Klafter F, Hirshman CA, Emala CW: A mechanism for rapacuronium-induced bronchospasm: M2 muscarinic receptor antagonism. Anesthesiology. 2003 Apr;98(4):906-11. [PubMed:12657852]

Drug created on September 11, 2007 15:43 / Updated on June 13, 2018 22:26