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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H61N2O4
Molecular Weight 597.8912
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of RAPACURONIUM

SMILES

CCC(=O)O[C@H]1[C@H](C[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)N5CCCCC5)[N+]6(CC=C)CCCCC6

InChI

InChIKey=HTIKWNNIPGXLGM-YLINKJIISA-N
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

HIDE SMILES / InChI

Description

Rapacuronium bromide (RAPLON), a nondepolarizing neuromuscular blocking agent, is a negative allosteric modulator of muscarinic acetylcholine receptors. Rapacuronium bromide is indicated as an adjunct to general anesthesia to facilitate tracheal intubation and to provide skeletal muscle relaxation during surgical procedures. There were no specific pharmacokinetic studies conducted to examine the drug-drug interactions of RAPLON. Due to the risk of fatal bronchospasm, it was withdrawn from the United States market less than 2 years after its FDA approval.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Time course of action and endotracheal intubating conditions of Org 9487, a new short-acting steroidal muscle relaxant; a comparison with succinylcholine.
1993 Sep
Preliminary investigations of the clinical pharmacology of three short-acting non-depolarizing neuromuscular blocking agents, Org 9453, Org 9489 and Org 9487.
1994 Mar
A mechanism for rapacuronium-induced bronchospasm: M2 muscarinic receptor antagonism.
2003 Apr
Rapacuronium preferentially antagonizes the function of M2 versus M3 muscarinic receptors in guinea pig airway smooth muscle.
2005 Jan
In silico prediction of blood brain barrier permeability: an Artificial Neural Network model.
2006 Jan-Feb
Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors.
2009 Dec 28
Determining the potency of neuromuscular blockers: are traditional methods flawed?
2010 Jun
Patents

Sample Use Guides

In Vivo Use Guide
The adult (1.5 mg/kg), pediatric (2.0 mg/kg), and Cesarean section (2.5 mg/kg)
Route of Administration: Intravenous
In Vitro Use Guide
Effects of 10 uM rapacuronium on the dissociation rate of high-affinity [3H]ACh binding were measured after 60 min preincubation of membranes with 40 nM [3H]ACh. Dissociation was evoked by the addition of unlabeled ACh at a final concentration of 40 uM, either alone or mixed with 10 uM rapacuronium. The slower phase of [3H]ACh dissociation displayed a rate (koff) in the range of 0.112 (M5) to 0.507 (M2) min-1.
Name Type Language
RAPACURONIUM
VANDF  
Common Name English
1-ALLYL-1-(3.ALPHA.,17.BETA.-DIHYDROXY-2.BETA.-PIPERIDINO-5.ALPHA.-ANDROSTAN-16.BETA.-YL)PIPERIDINIUM, 3-ACETATE 17-PROPIONATE
Common Name English
RAPACURONIUM CATION
Common Name English
RAPACURONIUM ION
Common Name English
ANDROSTANE-3,17-DIOL, 2-(1-PIPERIDINYL)-16-(1-(2-PROPENYL)-1-PIPERIDINIUMYL)-, 3-ACETATE 17-PROPANOATE, (2.BETA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-
Common Name English
RAPACURONIUM [VANDF]
Common Name English
Code System Code Type Description
RXCUI
262100
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY RxNorm
CAS
465499-11-0
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
MESH
C082938
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
EVMPD
SUB33903
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
WIKIPEDIA
RAPACURONIUM
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
PUBCHEM
5311399
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY