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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

[H][C@@]12C[C@@H]([C@H](OC(=O)CC)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](OC(C)=O)[C@H](C[C@]34C)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

Molecular Formula C37H61N2O4
Molecular Weight 597.8912
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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 Due to the risk of fatal bronchospasm, it was withdrawn from the United States market less than 2 years after its FDA approval.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

Targets

Primary TargetPharmacologyConditionPotency
4.3 null [pEC50]
4.55 null [pEC50]
4.12 null [pEC50]
9.69 null [pEC50]
4.21 null [pEC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RAPLON

Cmax

ValueDoseCo-administeredAnalytePopulation
7 μg/mL
0.6 mg/kg single, intravenous
RAPACURONIUM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
160 μg × min/mL
0.6 mg/kg single, intravenous
RAPACURONIUM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
70.3 min
0.6 mg/kg single, intravenous
RAPACURONIUM plasma
Homo sapiens
27.8 min
1.5 mg/kg 1 times / day steady-state, intravenous
RAPACURONIUM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
1.5 mg/kg 1 times / day steady-state, intravenous
RAPACURONIUM plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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.
Substance Class Chemical
Record UNII
GG1LBM463S
Record Status Validated (UNII)
Record Version