U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H57N2O4
Molecular Weight 557.8287
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of VECURONIUM

SMILES

CC(=O)O[C@@]1([H])C[C@]2([H])CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@@]([H])([C@]4([H])OC(=O)C)[N+]5(C)CCCCC5)[C@@]2(C)C[C@]1([H])N6CCCCC6

InChI

InChIKey=BGSZAXLLHYERSY-XQIGCQGXSA-N
InChI=1S/C34H57N2O4/c1-23(37)39-31-20-25-12-13-26-27(34(25,4)22-29(31)35-16-8-6-9-17-35)14-15-33(3)28(26)21-30(32(33)40-24(2)38)36(5)18-10-7-11-19-36/h25-32H,6-22H2,1-5H3/q+1/t25-,26+,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/075549s009lbl.pdf

Vecuronium is a neuromuscular blocking agent. Vecuronium operates by competing for the cholinoceptors at the motor end plate thereby exerting its muscle-relaxing properties which are used adjunctively to general anesthesia. Vecuronium is a bisquaternary nitrogen compound that acts by competitively binding to nicotinic cholinergic receptors. The binding of vecuronium decreases the opportunity for acetylcholine to bind to the nicotinic receptor at the postjunctional membrane of the myoneural junction. As a result, depolarization is prevented, calcium ions are not released and muscle contraction does not occur. Vecuronium is indicated as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Vecuronium bromide

Approved Use

Vecuronium bromide is indicated as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Launch Date

4.52044784E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1200 ng/mL
100 μg/kg bw single, intravenous
dose: 100 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VECURONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
29.5 μg × min/mL
100 μg/kg bw single, intravenous
dose: 100 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VECURONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
49.8 h
100 μg/kg bw single, intravenous
dose: 100 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VECURONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
75 min
unknown
VECURONIUM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
unknown
VECURONIUM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 mg single, intravenous
Overdose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources:
unhealthy, 2 months
n = 1
Health Status: unhealthy
Condition: anesthesia
Age Group: 2 months
Sex: M
Population Size: 1
Sources:
Disc. AE: Paralysis...
AEs leading to
discontinuation/dose reduction:
Paralysis (1 patient)
Sources:
0.12 mg/kg single, intravenous
Dose: 0.12 mg/kg
Route: intravenous
Route: single
Dose: 0.12 mg/kg
Sources:
unhealthy, 23 - 58 years
n = 20
Health Status: unhealthy
Condition: 27-81% total body surface area (TBSA) burn
Age Group: 23 - 58 years
Sex: unknown
Population Size: 20
Sources:
37 mg single, intravenous
Overdose
Dose: 37 mg
Route: intravenous
Route: single
Dose: 37 mg
Sources:
unhealthy, 23 months
n = 1
Health Status: unhealthy
Condition: Down’s syndrome had corrective cardiac surgery for an atrioventricular canal defect
Age Group: 23 months
Sex: unknown
Population Size: 1
Sources:
Disc. AE: Sepsis...
AEs leading to
discontinuation/dose reduction:
Sepsis (grade 5, 1 patient)
Sources:
0.112 mg/kg single, intravenous
Dose: 0.112 mg/kg
Route: intravenous
Route: single
Dose: 0.112 mg/kg
Sources:
unknown, adult
n = 1
Health Status: unknown
Age Group: adult
Sex: unknown
Population Size: 1
Sources:
Other AEs: Bradycardia...
Other AEs:
Bradycardia
Sources:
AEs

AEs

AESignificanceDosePopulation
Paralysis 1 patient
Disc. AE
5 mg single, intravenous
Overdose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources:
unhealthy, 2 months
n = 1
Health Status: unhealthy
Condition: anesthesia
Age Group: 2 months
Sex: M
Population Size: 1
Sources:
Sepsis grade 5, 1 patient
Disc. AE
37 mg single, intravenous
Overdose
Dose: 37 mg
Route: intravenous
Route: single
Dose: 37 mg
Sources:
unhealthy, 23 months
n = 1
Health Status: unhealthy
Condition: Down’s syndrome had corrective cardiac surgery for an atrioventricular canal defect
Age Group: 23 months
Sex: unknown
Population Size: 1
Sources:
Bradycardia
0.112 mg/kg single, intravenous
Dose: 0.112 mg/kg
Route: intravenous
Route: single
Dose: 0.112 mg/kg
Sources:
unknown, adult
n = 1
Health Status: unknown
Age Group: adult
Sex: unknown
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1.9 uM]
yes [IC50 127 uM]
yes [IC50 25.2 uM]
yes [IC50 3.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Muscle relaxants in paediatric day case surgery.
2001
Recent advances in myorelaxant therapy.
2001
Newer neuromuscular blocking agents: how do they compare with established agents?
2001
Acute respiratory and metabolic acidosis induced by excessive muscle contraction during spinal evoked stimulation.
2001 Apr
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.
2001 Apr
[A case of awareness during propofol anesthesia using bispectral index as an indicator of hypnotic effect].
2001 Aug
[The influence of age on hemodynamics and the dose requirements of propofol and buprenorphine in total intravenous anesthesia combined with continuous epidural anesthesia].
2001 Aug
Small dose of prostaglandin E(1) increases cardiac output without altering blood volume.
2001 Aug
Lightwand intubation is associated with less hemodynamic changes than fibreoptic intubation in normotensive, but not in hypertensive patients over the age of 60.
2001 Dec
The laryngeal mask airway is effective (and probably safe) in selected healthy parturients for elective Cesarean section: a prospective study of 1067 cases.
2001 Dec
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.
2001 Dec
Pharmacokinetics and pharmacodynamics of vecuronium in children receiving phenytoin or carbamazepine for chronic anticonvulsant therapy.
2001 Feb
Rapacuronium administration to patients receiving phenytoin or carbamazepine.
2001 Jul
Stimulated single fiber electromyography in the mouse: techniques and normative data.
2001 Jul
Vaginal physiological changes in a model of sexual arousal in anesthetized rats.
2001 Jul
Infusion of amino acid enriched solution hastens recovery from neuromuscular block caused by vecuronium.
2001 Jun
Oesophageal Doppler monitoring overestimates cardiac output during lumbar epidural anaesthesia.
2001 Jun
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.
2001 Jun
First fatal case of enterovirus 71 infection in Hong Kong.
2001 Jun
Anesthetic considerations in a patient with visceral leishmaniasis.
2001 Jun
Undiagnosed myasthenia gravis unmasked by neuromuscular blockade.
2001 May
Rocuronium: high risk for anaphylaxis?
2001 May
Cesarean section in a patient with syringomyelia.
2001 May
How serious is the bronchospasm induced by rapacuronium?
2001 May
A case of awareness with sevoflurane and epidural anesthesia in ovarian tumorectomy.
2001 May
Increased sensitivity to vecuronium and prolonged duration of its action in patients with end-stage renal failure.
2001 May
[Two pediatric cases of malignant hyperthermia caused by sevoflurane].
2001 Nov
Drug wastage contributes significantly to the cost of routine anesthesia care.
2001 Nov
Use of rapacuronium in a child with spinal muscular atrophy.
2001 Nov
Precurarization and priming: a theoretical analysis of safety and timing.
2001 Nov
The influence of deliberate hypotension on splanchnic perfusion balance with use of either isoflurane or esmolol and nitroglycerin.
2001 Nov
Rapacuronium for neuromuscular blockade in two myasthenic patients undergoing trans-sternal thymectomy.
2001 Nov
Is succinylcholine appropriate or obsolete in the intensive care unit?
2001 Oct
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery.
2001 Oct
Severe bradycardia during epilepsy surgery.
2001 Oct
[Anesthesia for a patient with alcoholic heart disease and transient complete heart block].
2001 Oct
[Improvement in oxygenation by alpha stimulant].
2001 Oct
[Anesthetic management of a patient with Dyggve-Melchior-Clausen syndrome].
2001 Oct
The bispectral index during an anaphylactic circulatory arrest.
2001 Oct
Effects of rapacuronium on respiratory function during general anesthesia: a comparison with cis-atracurium.
2001 Oct
Extremely prolonged vecuronium clearance in a brain death case.
2001 Oct
Systemic spread of vecuronium following use in peribulbar regional anaesthesia.
2001 Oct
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.
2001 Oct
[The effects of the fat component of propofol solution of ketogenesis during propofol anesthesia].
2001 Sep
Comparison between sevoflurane and propofol neuromuscular effects in a patient with myasthenia gravis: effective doses of vecuronium.
2001 Sep
Different patterns of mast cell activation by muscle relaxants in human skin.
2001 Sep
Tracheal lidocaine attenuates the cardiovascular response to endotracheal intubation.
2001 Sep
Vecuronium-associated axonal motor neuropathy: a variant of critical illness polyneuropathy?
2001 Sep
"Rap" in the streets: a retrospective look at the use of rapacuronium for prehospital rapid sequence induction.
2001 Sep-Oct
Nasotracheal intubation: a randomized trial of two methods.
2002 Jan
Patents

Sample Use Guides

In Vivo Use Guide
The recommended initial dose of Vecuronium is 0.08 to 0.1 mg/kg (1.4 to 1.75 times the ED90) given as an intravenous bolus injection. This dose can be expected to produce good or excellent non-emergency intubation conditions in 2.5 to 3 minutes after injection. Under balanced anesthesia, clinically required neuromuscular blockade lasts approximately 25-30 minutes, with recovery to 25% of control achieved approximately 25 to 40 minutes after injection and recovery to 95% of control achieved approximately 45-65 minutes after injection. In the presence of potent inhalation anesthetics, the neuromuscular blocking effect of Vecuronium is enhanced. If Vecuronium is first administered more than 5 minutes after the start of inhalation agent or when steady-state has been achieved, the initial Vecuronium bromide dose may be reduced by approximately 15%, i.e., 0.06 to 0.085 mg/kg.
Route of Administration: Intravenous
Magnesium sulfate at the concentrations of 1, 3, and 6 umol/L markedly enhanced the inhibition of vecuronium (10 nmol/L) on adult muscle-type acetylcholine receptors expressed in HEK293 cells.
Name Type Language
VECURONIUM
VANDF   WHO-DD  
Common Name English
ANDROSTANE-3,17-DIOL, 16-(1-METHYL-1-PIPERIDINIUMYL)-2-(1-PIPERIDINYL)-, DIACETATE (ESTER), (2.BETA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-
Common Name English
VECURONIUM [VANDF]
Common Name English
PIPERIDINIUM, 1-((2.BETA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-3,17-BIS(ACETYLOXY)-2-(1-PIPERIDINYL)ANDROSTAN-16-YL)-1-METHYL-
Common Name English
VECURONIUM [WHO-DD]
Common Name English
1-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3,17-DIACETOXY-10,13-DIMETHYL-2-PIPERIDIN-1-YLHEXADECAHYDRO-1H-CYCLOPENTA(A)PHENANTHREN-16-YL)-1-METHYLPIPERIDINIUM
Common Name English
VECURONIUM CATION
Common Name English
VECURONIUM ION
Common Name English
1-(3.ALPHA.,17.BETA.-DIHYDROXY-2.BETA.-PIPERIDINO-5.ALPHA.-ANDROSTAN-16.BETA.,5.ALPHA.-YL)-1-METHYLPIPERIDINIUM, DIACETATE
Common Name English
Classification Tree Code System Code
WHO-ATC M03AC03
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
WHO-VATC QM03AC03
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
NDF-RT N0000175720
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
NCI_THESAURUS C66886
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
NDF-RT N0000175732
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
Code System Code Type Description
WIKIPEDIA
Vecuronium
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
NCI_THESAURUS
C87317
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
FDA UNII
5438723848
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
EPA CompTox
86029-43-8
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
RXCUI
71535
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
ALTERNATIVE
CAS
86029-43-8
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
IUPHAR
4002
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
DRUG BANK
DB01339
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
PUBCHEM
39765
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
LACTMED
Vecuronium
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
EVMPD
SUB05084MIG
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
RXCUI
1546399
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY
DRUG CENTRAL
2811
Created by admin on Sat Jun 26 15:45:16 UTC 2021 , Edited by admin on Sat Jun 26 15:45:16 UTC 2021
PRIMARY