VECURONIUM

First approved in 1981

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 Search

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
Sources: https://www.drugbank.ca/drugs/DB01339
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17525594 \| https://www.ncbi.nlm.nih.gov/pubmed/18633030 \| https://www.ncbi.nlm.nih.gov/pubmed/19417616	Antagonist 2760		8.7 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postoperative complications 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/075549s009lbl.pdf	Palliative		Approved 8360	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

C_max

Value	Dose	Co-administered	Analyte	Population
1200 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2875724/	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

Value	Dose	Co-administered	Analyte	Population
29.5 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2875724/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
49.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2875724/	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/075549s013lbl.pdf	unknown		VECURONIUM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/075549s013lbl.pdf	unknown		VECURONIUM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 mg single, intravenous Overdose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15794110/	unhealthy, 2 months n = 1 Health Status: unhealthy Condition: anesthesia Age Group: 2 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15794110/	Disc. AE: Paralysis... AEs leading to discontinuation/dose reduction: Paralysis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15794110/
0.12 mg/kg single, intravenous Dose: 0.12 mg/kg Route: intravenous Route: single Dose: 0.12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/24067332/	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: https://pubmed.ncbi.nlm.nih.gov/24067332/	Sources: https://pubmed.ncbi.nlm.nih.gov/24067332/
37 mg single, intravenous Overdose Dose: 37 mg Route: intravenous Route: single Dose: 37 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1979208/	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: https://pubmed.ncbi.nlm.nih.gov/1979208/	Disc. AE: Sepsis... AEs leading to discontinuation/dose reduction: Sepsis (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/1979208/
0.112 mg/kg single, intravenous Dose: 0.112 mg/kg Route: intravenous Route: single Dose: 0.112 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/	unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/	Other AEs: Bradycardia... Other AEs: Bradycardia Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/

AEs

AE	Significance	Dose	Population
Paralysis	1 patient Disc. AE	5 mg single, intravenous Overdose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15794110/	unhealthy, 2 months n = 1 Health Status: unhealthy Condition: anesthesia Age Group: 2 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15794110/
Sepsis	grade 5, 1 patient Disc. AE	37 mg single, intravenous Overdose Dose: 37 mg Route: intravenous Route: single Dose: 37 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1979208/	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: https://pubmed.ncbi.nlm.nih.gov/1979208/
Bradycardia		0.112 mg/kg single, intravenous Dose: 0.112 mg/kg Route: intravenous Route: single Dose: 0.112 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/	unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 638 MATE1 304 MATE2 261 OCT1 506	P-gp 1527

Drug as perpetrator

Target	Modality	Activity
MATE1 306	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 1.9 uM]
OCT1 523	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/9187257/	yes [IC50 127 uM]
MATE2 261	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 25.2 uM]
OCT2 639	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 3.5 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1527	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/9655875/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9939	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9939
ZINC	ZINC000004097404	http://zinc15.docking.org/substances/ZINC000004097404

PubMed

Title	Date	PubMed
Muscle relaxants in paediatric day case surgery.	2001	11766247
The acute effects of body position strategies and respiratory therapy in paralyzed patients with acute lung injury.	2001	11299066
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.	2001 Apr	11456272
Inhaled nitric oxide administration during one-lung ventilation in patients undergoing thoracic surgery.	2001 Apr	11312483
Vital capacity inhalation induction with sevoflurane: an alternative to standard intravenous induction for patients undergoing cardiac surgery.	2001 Apr	11312473
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.	2001 Apr	11312471
Torticollis following induction of anaesthesia.	2001 Apr	11284852
Effect of halothane on the cerebral circulation in young children: a hysteresis phenomenon.	2001 Apr	11284825
[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	11554014
Small dose of prostaglandin E(1) increases cardiac output without altering blood volume.	2001 Aug	11498312
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department.	2001 Aug	11493818
A multicenter evaluation of the time-course of action of two doses of rapacuronium after early and late reversal with neostigmine.	2001 Aug	11473863
The pharmacoeconomics of neuromuscular blocking drugs: a perioperative cost-minimization strategy in children.	2001 Aug	11473856
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	11744593
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	11744589
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.	2001 Dec	11737923
Precipitation of thiopental by rapacuronium.	2001 Jul	11465575
Vaginal physiological changes in a model of sexual arousal in anesthetized rats.	2001 Jul	11404287
[Intracerebral hemorrhage induced by cerebral amyloid angiopathy in a patient during transurethral electrocoagulation].	2001 Jun	11452474
[Anesthesia using propofol for a patient with arthrogryposis multiplex congenita].	2001 Jun	11452472
Anesthetic considerations in a patient with visceral leishmaniasis.	2001 Jun	11444445
Pediatric renal transplantation: anesthesia and perioperative complications.	2001 Mar	11315282
[Perioperative administration of bicarbonated solution to a patient with mitochondrial encephalomyopathy].	2001 Mar	11296447
[Droperidol and dimenhydrinate alone or in combination for prevention of postoperative nausea and vomiting].	2001 May	11413698
Cesarean section in a patient with syringomyelia.	2001 May	11394517
Bronchospasm after rapacuronium in infants and children.	2001 May	11388548
How serious is the bronchospasm induced by rapacuronium?	2001 May	11388547
Severe bronchospasm and desaturation in a child associated with rapacuronium.	2001 May	11388546
Rapacuronium and bronchospasm.	2001 May	11388519
Duration of action of vecuronium after an intubating dose of rapacuronium, vecuronium, or succinylcholine.	2001 May	11323346
Comparison of genotoxicity of sevoflurane and isoflurane in human lymphocytes studied in vivo using the comet assay.	2001 May 31	11377249
[Two pediatric cases of malignant hyperthermia caused by sevoflurane].	2001 Nov	11758332
Drug wastage contributes significantly to the cost of routine anesthesia care.	2001 Nov	11704446
Use of rapacuronium in a child with spinal muscular atrophy.	2001 Nov	11696151
Precurarization and priming: a theoretical analysis of safety and timing.	2001 Nov	11682407
The influence of deliberate hypotension on splanchnic perfusion balance with use of either isoflurane or esmolol and nitroglycerin.	2001 Nov	11682378
Rapacuronium for neuromuscular blockade in two myasthenic patients undergoing trans-sternal thymectomy.	2001 Nov	11580788
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001 Oct	11737897
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery.	2001 Oct	11737170
[Improvement in oxygenation by alpha stimulant].	2001 Oct	11712347
The bispectral index during an anaphylactic circulatory arrest.	2001 Oct	11669440
Effects of rapacuronium on respiratory function during general anesthesia: a comparison with cis-atracurium.	2001 Oct	11605931
Extremely prolonged vecuronium clearance in a brain death case.	2001 Oct	11605900
Systemic spread of vecuronium following use in peribulbar regional anaesthesia.	2001 Oct	11576132
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.	2001 Oct	11574363
[The effects of the fat component of propofol solution of ketogenesis during propofol anesthesia].	2001 Sep	11593719
Comparison between sevoflurane and propofol neuromuscular effects in a patient with myasthenia gravis: effective doses of vecuronium.	2001 Sep	11575561
Different patterns of mast cell activation by muscle relaxants in human skin.	2001 Sep	11575539
Tracheal lidocaine attenuates the cardiovascular response to endotracheal intubation.	2001 Sep	11546711
Nasotracheal intubation: a randomized trial of two methods.	2002 Jan	11753001

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

In Vitro Use Guide

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

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