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

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H57N2O4
Molecular Weight 557.8274
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of VECURONIUM

SMILES

[H][C@@]12C[C@@H]([C@H](OC(C)=O)[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(C)CCCCC6

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
Recent advances in myorelaxant therapy.
2001
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.
2001 Apr
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.
2001 Apr
Effect of halothane on the cerebral circulation in young children: a hysteresis phenomenon.
2001 Apr
Overdistension in ventilated children.
2001 Aug
Small dose of prostaglandin E(1) increases cardiac output without altering blood volume.
2001 Aug
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department.
2001 Aug
A multicenter evaluation of the time-course of action of two doses of rapacuronium after early and late reversal with neostigmine.
2001 Aug
Unmasked residual neuromuscular block after administration of vecuronium for days.
2001 Aug
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
Pharmacokinetics and pharmacodynamics of vecuronium in children receiving phenytoin or carbamazepine for chronic anticonvulsant therapy.
2001 Feb
Comparison of no airway device, the Guedel-type airway and the Cuffed Oropharyngeal Airway with mask ventilation during manual in-line stabilization.
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
2001 Feb
Nicorandil accelerates recovery of neuromuscular block caused by vecuronium.
2001 Jan
[A case of ventricular tachycardia immediately after electroconvulsive therapy in a schinzophrenic patient].
2001 Jan
[Pulmonary embolism during laparoscopic cholecystectomy detected by sudden decrease in end-tidal carbon dioxide pressure].
2001 Jan
Vaginal physiological changes in a model of sexual arousal in anesthetized rats.
2001 Jul
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.
2001 Jun
Pediatric renal transplantation: anesthesia and perioperative complications.
2001 Mar
[Perioperative administration of bicarbonated solution to a patient with mitochondrial encephalomyopathy].
2001 Mar
Cesarean section in a patient with syringomyelia.
2001 May
Severe bronchospasm and desaturation in a child associated with rapacuronium.
2001 May
Rapacuronium and bronchospasm.
2001 May
A case of awareness with sevoflurane and epidural anesthesia in ovarian tumorectomy.
2001 May
[Two pediatric cases of malignant hyperthermia caused by sevoflurane].
2001 Nov
Severe bradycardia during epilepsy surgery.
2001 Oct
[Anesthesia for a patient with alcoholic heart disease and transient complete heart block].
2001 Oct
[Anesthetic management of a patient with Dyggve-Melchior-Clausen syndrome].
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
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
Vecuronium [WHO-DD]
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
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 Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
WHO-VATC QM03AC03
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
NDF-RT N0000175720
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
NDF-RT N0000175732
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
Code System Code Type Description
WIKIPEDIA
Vecuronium
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
DAILYMED
5438723848
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
NCI_THESAURUS
C87317
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
FDA UNII
5438723848
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID1044146
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
RXCUI
71535
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
ALTERNATIVE
CAS
86029-43-8
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
IUPHAR
4002
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
DRUG BANK
DB01339
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
SMS_ID
100000087879
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
PUBCHEM
39765
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
LACTMED
Vecuronium
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
EVMPD
SUB05084MIG
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
RXCUI
1546399
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY
DRUG CENTRAL
2811
Created by admin on Fri Dec 15 16:29:58 UTC 2023 , Edited by admin on Fri Dec 15 16:29:58 UTC 2023
PRIMARY