VECURONIUM BROMIDE

First approved in 1981

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H57N2O4.Br
Molecular Weight	637.731
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CC(=O)O[C@H]1[C@H](C[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)N5CCCCC5)[N+]6(C)CCCCC6

InChI

InChIKey=VEPSYABRBFXYIB-PWXDFCLTSA-M

InChI=1S/C34H57N2O4.BrH/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;1H/q+1;/p-1/t25-,26+,27-,28-,29-,30-,31-,32-,33-,34-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C34H57N2O4
Molecular Weight	557.8274
Charge	1
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 11
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 2849		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 8583	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 1984

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 Health Status: unhealthy Age Group: 2 months Sex: M 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 Health Status: unhealthy Age Group: 23 - 58 years Sex: unknown 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 Health Status: unhealthy Age Group: 23 months Sex: unknown 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 Health Status: unknown Age Group: adult Sex: unknown 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 Health Status: unhealthy Age Group: 2 months Sex: M 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 Health Status: unhealthy Age Group: 23 months Sex: unknown 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 Health Status: unknown Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/2901271/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 779 MATE1 415 MATE2 267 OCT1 620	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 1.9 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9187257/	yes [IC50 127 uM]
MATE2 267	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 25.2 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 3.5 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 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
Nasotracheal intubation: a randomized trial of two methods.	2002-01	11753001
Lightwand intubation is associated with less hemodynamic changes than fibreoptic intubation in normotensive, but not in hypertensive patients over the age of 60.	2001-12	11744593
The laryngeal mask airway is effective (and probably safe) in selected healthy parturients for elective Cesarean section: a prospective study of 1067 cases.	2001-12	11744589
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.	2001-12	11737923
[Two pediatric cases of malignant hyperthermia caused by sevoflurane].	2001-11	11758332
Drug wastage contributes significantly to the cost of routine anesthesia care.	2001-11	11704446
Use of rapacuronium in a child with spinal muscular atrophy.	2001-11	11696151
Precurarization and priming: a theoretical analysis of safety and timing.	2001-11	11682407
The influence of deliberate hypotension on splanchnic perfusion balance with use of either isoflurane or esmolol and nitroglycerin.	2001-11	11682378
Rapacuronium for neuromuscular blockade in two myasthenic patients undergoing trans-sternal thymectomy.	2001-11	11580788
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001-10	11737897
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery.	2001-10	11737170
Severe bradycardia during epilepsy surgery.	2001-10	11733666
[Anesthesia for a patient with alcoholic heart disease and transient complete heart block].	2001-10	11712350
[Improvement in oxygenation by alpha stimulant].	2001-10	11712347
[Anesthetic management of a patient with Dyggve-Melchior-Clausen syndrome].	2001-10	11712346
The bispectral index during an anaphylactic circulatory arrest.	2001-10	11669440
Effects of rapacuronium on respiratory function during general anesthesia: a comparison with cis-atracurium.	2001-10	11605931
Extremely prolonged vecuronium clearance in a brain death case.	2001-10	11605900
Systemic spread of vecuronium following use in peribulbar regional anaesthesia.	2001-10	11576132
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.	2001-10	11574363
"Rap" in the streets: a retrospective look at the use of rapacuronium for prehospital rapid sequence induction.	2001-09-12	11552106
[The effects of the fat component of propofol solution of ketogenesis during propofol anesthesia].	2001-09	11593719
Comparison between sevoflurane and propofol neuromuscular effects in a patient with myasthenia gravis: effective doses of vecuronium.	2001-09	11575561
Different patterns of mast cell activation by muscle relaxants in human skin.	2001-09	11575539
Tracheal lidocaine attenuates the cardiovascular response to endotracheal intubation.	2001-09	11546711
Vecuronium-associated axonal motor neuropathy: a variant of critical illness polyneuropathy?	2001-09	11525888
[A case of awareness during propofol anesthesia using bispectral index as an indicator of hypnotic effect].	2001-08	11554023
[The influence of age on hemodynamics and the dose requirements of propofol and buprenorphine in total intravenous anesthesia combined with continuous epidural anesthesia].	2001-08	11554014
Airway pressure release ventilation increases cardiac performance in patients with acute lung injury/adult respiratory distress syndrome.	2001-08	11511336
Overdistension in ventilated children.	2001-08	11511332
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms.	2001-08	11506123
Small dose of prostaglandin E(1) increases cardiac output without altering blood volume.	2001-08	11498312
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department.	2001-08	11493818
A multicenter evaluation of the time-course of action of two doses of rapacuronium after early and late reversal with neostigmine.	2001-08	11473863
Unmasked residual neuromuscular block after administration of vecuronium for days.	2001-08	11473857
The pharmacoeconomics of neuromuscular blocking drugs: a perioperative cost-minimization strategy in children.	2001-08	11473856
Precipitation of thiopental by rapacuronium.	2001-07	11465575
Infusion of amino acid enriched solution hastens recovery from neuromuscular block caused by vecuronium.	2001-06	11573589
Oesophageal Doppler monitoring overestimates cardiac output during lumbar epidural anaesthesia.	2001-06	11573585
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.	2001-06	11533541
First fatal case of enterovirus 71 infection in Hong Kong.	2001-06	11514756
Undiagnosed myasthenia gravis unmasked by neuromuscular blockade.	2001-05	11575353
Rocuronium: high risk for anaphylaxis?	2001-05	11575345
Acute respiratory and metabolic acidosis induced by excessive muscle contraction during spinal evoked stimulation.	2001-04	11573641
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.	2001-04	11456272
Pharmacokinetics and pharmacodynamics of vecuronium in children receiving phenytoin or carbamazepine for chronic anticonvulsant therapy.	2001-02	11573664
Muscle relaxants in paediatric day case surgery.	2001	11766247
Recent advances in myorelaxant therapy.	2001	11696115
[Rocuronium or vecuronium for intubation for short operations in the preschool age? Effects on time in the operating room and postoperative phase].	2001	11455866

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 `Mon Mar 31 21:28:05 GMT 2025` Edited by `admin` on `Mon Mar 31 21:28:05 GMT 2025`
Record UNII	7E4PHP5N1D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VECURONIUM BROMIDE

Official Name

English

NORCURON

Preferred Name

English

VECURONIUM BROMIDE [EP IMPURITY]

Common Name

English

VECURONIUM BROMIDE [ORANGE BOOK]

Common Name

English

Vecuronium bromide [WHO-DD]

Common Name

English

VECURONIUM BROMIDE [JAN]

Common Name

English

1-(3?,17?-Dihydroxy-2?-piperidino-5?-androstan-16?,5?-yl)-1-methylpiperidinium bromide, diacetate

Common Name

English

PANCURONIUM BROMIDE IMPURITY D [EP IMPURITY]

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-, BROMIDE

Common Name

English

VECURONIUM BROMIDE [MART.]

Common Name

English

VECURONIUM BROMIDE [USP MONOGRAPH]

Common Name

English

VECURONIUM BROMIDE [EP MONOGRAPH]

Common Name

English

VECURONIUM BROMIDE [MI]

Common Name

English

ORG-NC 45

Code

English

PANCURONIUM BROMIDE IMPURITY, VECURONIUM BROMIDE - [USP IMPURITY]

Common Name

English

VECURONIUM BROMIDE [VANDF]

Common Name

English

NSC-759184

Code

English

VECURONIUM BROMIDE [USAN]

Common Name

English

VECURONIUM BROMIDE [USP-RS]

Common Name

English

vecuronium bromide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29696