Identification

Summary

Vecuronium is a nondepolarizing neuromuscular blocking agent used to relax muscles or as an adjunct in general anesthesia during surgical procedures.

Generic Name
Vecuronium
DrugBank Accession Number
DB01339
Background

Monoquaternary homolog of pancuronium. A non-depolarizing neuromuscular blocking agent with shorter duration of action than pancuronium. Its lack of significant cardiovascular effects and lack of dependence on good kidney function for elimination as well as its short duration of action and easy reversibility provide advantages over, or alternatives to, other established neuromuscular blocking agents.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 557.8274
Monoisotopic: 557.431833322
Chemical Formula
C34H57N2O4
Synonyms
  • Vecuronio
  • Vecuronium cation

Pharmacology

Indication

Vecuronium is a muscle relaxing agent and is used as an adjunct in general anesthesia.

Pharmacology
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Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

The principal pharmacologic effects demonstrated by vecuronium revolve around its competitive binding of cholinergic receptors located at motor end plates. This competitive binding results in muscle relaxant effects that are typically employed as an adjunct to general anesthesia.

Mechanism of action

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.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

100%

Route of elimination

Fecal (40-75%) and renal (30% as unchanged drug and metabolites)

Half-life

51–80 minutes

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Vecuronium.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Vecuronium.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Vecuronium is combined with Acetyldigitoxin.
AclidiniumVecuronium may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Vecuronium is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Vecuronium is combined with Alfentanil.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Vecuronium.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Vecuronium.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Vecuronium.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Vecuronium bromide7E4PHP5N1D50700-72-6VEPSYABRBFXYIB-PWXDFCLTSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NorcuronInjection, powder, lyophilized, for solution10 mg/1IntravenousOrganon1984-04-302002-06-25US flag
Norcuron Inj 10mg/vialPowder, for solution10 mg / vialIntravenousOrganon Canada Ltd Ltee1986-12-312009-08-04Canada flag
Vecuronium BromideInjection, powder, lyophilized, for solution10 mg/1IntravenousWatson Pharmaceuticals2007-06-25Not applicableUS flag
Vecuronium Bromide for InjectionPowder, for solution20.00 mg / vialIntravenousHospira Healthcare Ulc2000-01-282018-11-29Canada flag
Vecuronium Bromide for InjectionPowder, for solution10 mg / vialIntravenousPartners Health Care, Inc.2000-06-132008-02-15Canada flag
Vecuronium Bromide for InjectionPowder, for solution10.00 mg / vialIntravenousHospira Healthcare Ulc2000-06-012018-11-29Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Vecuronium BromideInjection, powder, for solution20 mg/1IntravenousHikma Pharmaceuticals USA Inc.2019-08-01Not applicableUS flag
Vecuronium bromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousAkorn - Strides LLC2010-09-15Not applicableUS flag
Vecuronium BromideInjection, powder, lyophilized, for solution10 mg/10mLIntravenousCardinal Health1999-08-252012-08-31US flag
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousCardinal Health2009-07-212015-07-31US flag
Vecuronium BromideInjection, powder, lyophilized, for solution20 mg/20mLIntravenousTeva Parenteral Medicines, Inc.2002-11-14Not applicableUS flag
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousSun Pharmaceutical Industries, Inc.2014-12-15Not applicableUS flag
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousMylan Institutional LLC2011-05-112018-03-31US flag
Vecuronium BromideInjection, powder, lyophilized, for solution20 mg/1IntravenousAuroMedics Pharma LLC2018-12-20Not applicableUS flag
Vecuronium BromideInjection, powder, lyophilized, for solution5 mg/1mLIntravenousBedford Pharmaceuticals2008-08-112010-04-30US flag
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousSun Pharma Global Inc.2014-12-152016-01-31US flag

Categories

ATC Codes
M03AC03 — Vecuronium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androstane steroids / Piperidines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts
show 4 more
Substituents
Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Androstane-skeleton / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Hydrocarbon derivative
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
quaternary ammonium ion, acetate ester, androstane (CHEBI:9939)
Affected organisms
Not Available

Chemical Identifiers

UNII
5438723848
CAS number
86029-43-8
InChI Key
BGSZAXLLHYERSY-XQIGCQGXSA-N
InChI
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
IUPAC Name
1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]-1-methylpiperidin-1-ium
SMILES
[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC1

References

Synthesis Reference

Frans Herwig Jan Jansen, "Process to prepare pharmaceutical compositions containing vecuronium bromide and compositions produced thereby." U.S. Patent US5681573, issued January, 1969.

US5681573
General References
  1. FDA Approved Drug Products: vecuronium bromide injection [Link]
Human Metabolome Database
HMDB0015432
KEGG Compound
C07553
PubChem Compound
39765
PubChem Substance
46507656
ChemSpider
36358
BindingDB
50424713
RxNav
71535
ChEBI
9939
ChEMBL
CHEMBL1201219
ZINC
ZINC000004097404
Therapeutic Targets Database
DAP000354
PharmGKB
PA164748865
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vecuronium_bromide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherArthropathy of Hip1
4CompletedTreatmentAnaesthesia therapy1
4CompletedTreatmentAvascular Necrosis / Inflammatory Arthritis / Opioids Use / Osteoarthritis of the Shoulder / Rotator Cuff Tears1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentNeuromuscular Blockade1
4CompletedTreatmentReversal of Neuromuscular Blockade1
4Unknown StatusOtherPatients Undergoing Laparoscopic Surgery1
4Unknown StatusPreventionPost-Operative Confusion1
4Unknown StatusTreatmentCognitive Ability, General / Injuries, Brain1
4Unknown StatusTreatmentPerioperative/Postoperative Complications / PORC (Postoperative Residual Curarization)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • APP Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Cardinal Health
  • Hospira Inc.
  • Organon Pharmaceuticals
  • Pharmedium
  • Schein Pharmaceutical Inc.
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
  • Zhejiang Xianju Pharmaceutical Co. Ltd.
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous10 mg
SolutionParenteral4 mg
Injection, powder, for solutionIntravenous
Injection, powder, for solutionIntravenous10 MG
Injection, powder, for solutionIntravenous4 MG
PowderIntravenous
Injection, powder, lyophilized, for solutionIntravenous4 mg
Injection, powder, lyophilized, for solutionIntravenous4.0077 mg
Powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionParenteral10 mg
Injection, powder, for solutionIntravenous10 mg/1
Injection, powder, for solutionIntravenous20 mg/1
Injection, powder, lyophilized, for solutionIntravenous1 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous10 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous10 mg/1
Injection, powder, lyophilized, for solutionIntravenous20 mg/1
Injection, powder, lyophilized, for solutionIntravenous20 mg/20mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/1mL
Powder, for solutionIntravenous10 mg / vial
Powder, for solutionIntravenous10.00 mg / vial
Powder, for solutionIntravenous20.00 mg / vial
Prices
Unit descriptionCostUnit
Vecuronium 20 mg vial5.05USD vial
Vecuronium 10 mg vial3.64USD vial
Vecuronium 10 mg/10 ml syringe2.36USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.86e-05 mg/mLALOGPS
logP2.07ALOGPS
logP0.89ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)9.65ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity169.31 m3·mol-1ChemAxon
Polarizability66.85 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8913
Blood Brain Barrier+0.878
Caco-2 permeable+0.5457
P-glycoprotein substrateSubstrate0.77
P-glycoprotein inhibitor IInhibitor0.6962
P-glycoprotein inhibitor IIInhibitor0.6508
Renal organic cation transporterNon-inhibitor0.6862
CYP450 2C9 substrateNon-substrate0.8382
CYP450 2D6 substrateNon-substrate0.7638
CYP450 3A4 substrateSubstrate0.742
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9229
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9368
Ames testNon AMES toxic0.7499
CarcinogenicityNon-carcinogens0.9265
BiodegradationNot ready biodegradable0.8557
Rat acute toxicity2.6653 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9021
hERG inhibition (predictor II)Non-inhibitor0.7784
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0000090000-30783b30128b3c20c2ae
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0000090000-cd687d0e7ce4ae357aff
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0101090000-89eda364a0ed6638a666
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0pb9-1809120000-c2bee4083e6bf7f417b3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zfr-2904000000-2c0dfbec678d7b580771

Targets

Drugtargets2
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insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Jonsson Fagerlund M, Dabrowski M, Eriksson LI: Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52. doi: 10.1097/ALN.0b013e31819fade3. [Article]
  2. Liu M, Dilger JP: Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33. doi: 10.1213/ane.0b013e31817b4469. [Article]
  3. Paul M, Fokt RM, Kindler CH, Dipp NC, Yost CS: Characterization of the interactions between volatile anesthetics and neuromuscular blockers at the muscle nicotinic acetylcholine receptor. Anesth Analg. 2002 Aug;95(2):362-7, table of contents. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Smit JW, Weert B, Schinkel AH, Meijer DK: Heterologous expression of various P-glycoproteins in polarized epithelial cells induces directional transport of small (type 1) and bulky (type 2) cationic drugs. J Pharmacol Exp Ther. 1998 Jul;286(1):321-7. [Article]

Drug created at June 30, 2007 18:08 / Updated at December 01, 2021 01:05