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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H61N2O4
Molecular Weight 597.8926
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of RAPACURONIUM

SMILES

C=CC[N+]1(CCCCC1)[C@@]2([H])C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@]([H])([C@]([H])(C[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]2([H])OC(=O)CC)N6CCCCC6)OC(=O)C

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
Curator's Comment:: http://www.rxlist.com/raplon-drug.htm | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=43578

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 Due to the risk of fatal bronchospasm, it was withdrawn from the United States market less than 2 years after its FDA approval.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RAPLON

Approved Use

RAPLON™ (rapacuronium bromide) for Injection is indicated as an adjunct to general anesthesia to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgical procedures.

Launch Date

934848000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7 μg/mL
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPACURONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
160 μg × min/mL
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPACURONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
70.3 min
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPACURONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
27.8 min
1.5 mg/kg 1 times / day steady-state, intravenous
dose: 1.5 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
RAPACURONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
1.5 mg/kg 1 times / day steady-state, intravenous
dose: 1.5 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
RAPACURONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Bronchospasm, Tachycardia...
Other AEs:
Bronchospasm (3.4%)
Tachycardia (1.6%)
Injection site reaction (1.1%)
Hypotension (0.9%)
Airway peak pressure increased (0.6%)
Erythematous rash (0.5%)
Hypertension (<0.1%)
Fever (<0.1%)
Nausea and vomiting (<0.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Erythematous rash 0.5%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Airway peak pressure increased 0.6%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Hypotension 0.9%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Injection site reaction 1.1%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Tachycardia 1.6%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Bronchospasm 3.4%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Fever <0.1%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Hypertension <0.1%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea and vomiting <0.1%
3 mg/kg single, intravenous
Recommended
Dose: 3 mg/kg
Route: intravenous
Route: single
Dose: 3 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
unlikely
Sourcing
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
Patents

Sample Use Guides

The adult (1.5 mg/kg), pediatric (2.0 mg/kg), and Cesarean section (2.5 mg/kg)
Route of Administration: Intravenous
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
DRUG CENTRAL
3520
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
DRUG BANK
DB04834
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
FDA UNII
GG1LBM463S
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
RXCUI
262100
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY RxNorm
CAS
465499-11-0
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
MESH
C082938
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
EVMPD
SUB33903
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
WIKIPEDIA
RAPACURONIUM
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY
PUBCHEM
5311399
Created by admin on Sat Jun 26 11:37:01 UTC 2021 , Edited by admin on Sat Jun 26 11:37:01 UTC 2021
PRIMARY