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

Molecular Formula	C34H57N2O4
Molecular Weight	557.8274
Charge	1
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Newer neuromuscular blocking agents: how do they compare with established agents?	2001	11434449
Acute respiratory and metabolic acidosis induced by excessive muscle contraction during spinal evoked stimulation.	2001 Apr	11573641
[Anesthetic management of the King-Denborough syndrome].	2001 Apr	11345752
Effect of halothane on the cerebral circulation in young children: a hysteresis phenomenon.	2001 Apr	11284825
Postoperative residual block after intermediate-acting neuromuscular blocking drugs.	2001 Apr	11284816
[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
Overdistension in ventilated children.	2001 Aug	11511332
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms.	2001 Aug	11506123
Small dose of prostaglandin E(1) increases cardiac output without altering blood volume.	2001 Aug	11498312
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
Intravenous ketamine attenuates arterial pressure changes during the induction of anaesthesia with propofol.	2001 Feb	11270030
Effect of hypothermia on the hepatic uptake and biliary excretion of vecuronium in the isolated perfused rat liver.	2001 Feb	11176092
[A case of ventricular tachycardia immediately after electroconvulsive therapy in a schinzophrenic patient].	2001 Jan	11211751
No substitute for the intravenous route.	2001 Jan	11135714
Vaginal physiological changes in a model of sexual arousal in anesthetized rats.	2001 Jul	11404287
Post-neonatal tetanus: issues in intensive care management.	2001 Mar	11338225
[Pulmonary edema in a child following laryngospasm triggered by a laryngeal mask airway during emergence from anesthesia].	2001 Mar	11296448
Cesarean section in a patient with syringomyelia.	2001 May	11394517
Rapacuronium and bronchospasm.	2001 May	11388519
Rapacuronium: an alternative to succinylcholine for electroconvulsive therapy.	2001 May	11323342
[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
Severe bradycardia during epilepsy surgery.	2001 Oct	11733666
[Anesthetic management of a patient with Dyggve-Melchior-Clausen syndrome].	2001 Oct	11712346
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
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.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:55:53 UTC 2023` Edited by `admin` on `Wed Jul 05 23:55:53 UTC 2023`
Record UNII	5438723848
Record Status	`Validated (UNII)`
Record Version

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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