Identification

Name
Vecuronium
Accession Number
DB01339
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Vecuronio
  • Vecuronium cation
Product Ingredients
IngredientUNIICASInChI Key
Vecuronium bromide7E4PHP5N1D50700-72-6VEPSYABRBFXYIB-PWXDFCLTSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NorcuronInjection, powder, lyophilized, for solution10 mg/1IntravenousOrganon1984-04-302002-06-25Us
Norcuron Inj 10mg/vialPowder, for solution10 mgIntravenousOrganon Canada Ltd Ltee1986-12-312009-08-04Canada
Vecuronium BromideInjection, powder, lyophilized, for solution10 mg/1IntravenousWatson Pharmaceuticals2007-06-25Not applicableUs
Vecuronium Bromide for InjectionPowder, for solution20.00 mgIntravenousHospira, Inc.2000-01-28Not applicableCanada
Vecuronium Bromide for InjectionPowder, for solution10 mgIntravenousPartners Health Care, Inc.2000-06-132008-02-15Canada
Vecuronium Bromide for InjectionPowder, for solution10.00 mgIntravenousHospira, Inc.2000-06-01Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VecuroniumInjection, powder, lyophilized, for solution20 mg/20mLIntravenousSagent Pharmaceuticals2011-08-01Not applicableUs
VecuroniumInjection, powder, lyophilized, for solution10 mg/10mLIntravenousSagent Pharmaceuticals2011-08-01Not applicableUs
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-112017-12-31Us
Vecuronium BromideInjection, powder, lyophilized, for solution5 mg/1mLIntravenousBedford Pharmaceuticals2008-06-022010-09-30Us
Vecuronium bromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousAkorn - Strides LLC2010-09-15Not applicableUs
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousRemedy Repack2015-06-192016-06-19Us
Vecuronium BromideInjection, powder, lyophilized, for solution20 mg/20mLIntravenousTeva Parenteral Medicines, Inc.2002-11-14Not applicableUs
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousSun Pharmaceutical Industries, Inc.2014-12-15Not applicableUs
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousSun Pharma Global Inc.2014-12-152016-01-31Us
Vecuronium BromideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousMylan Institutional2011-05-112018-07-12Us
Categories
UNII
5438723848
CAS number
86029-43-8
Weight
Average: 557.8274
Monoisotopic: 557.431833322
Chemical Formula
C34H57N2O4
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

Pharmacology

Indication

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

Associated Therapies
Pharmacodynamics

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.

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
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Vecuronium can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Vecuronium is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Vecuronium is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbemaciclibThe serum concentration of Vecuronium can be increased when it is combined with Abemaciclib.
AcepromazineThe risk or severity of adverse effects can be increased when Vecuronium is combined with Acepromazine.
Food Interactions
Not Available

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
Not Available
External Links
Human Metabolome Database
HMDB0015432
KEGG Compound
C07553
PubChem Compound
39765
PubChem Substance
46507656
ChemSpider
36358
BindingDB
50424713
ChEBI
9939
ChEMBL
CHEMBL1201219
Therapeutic Targets Database
DAP000354
PharmGKB
PA164748865
IUPHAR
4002
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vecuronium
ATC Codes
M03AC03 — Vecuronium
AHFS Codes
  • 12:20.20 — Neuromuscular Blocking Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAnaesthesia therapy1
4CompletedOtherArthropathy of Hip1
4CompletedTreatmentAnaesthesia therapy1
4CompletedTreatmentGall Stone Disease1
4Not Yet RecruitingOtherPatients Undergoing Laparoscopic Surgery1
4Unknown StatusTreatmentPerioperative/Postoperative Complications / PORC (Postoperative Residual Curarization)1
Not AvailableCompletedSupportive CareC.Delivery; Surgery (Previous), Gynecological / Delayed Emergence From Anesthesia / Inappropriate Device Stimulation of Tissue1

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, powder, lyophilized, for solutionIntravenous10 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous20 mg/20mL
Injection, powder, lyophilized, for solutionIntravenous1 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous10 mg/1
Injection, powder, lyophilized, for solutionIntravenous5 mg/1mL
Powder, for solutionIntravenous10 mg
Powder, for solutionIntravenous10.00 mg
Powder, for solutionIntravenous20.00 mg
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

Taxonomy

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
Steroid ester / Androstane-skeleton / Dicarboxylic acid or derivatives / Piperidine / Quaternary ammonium salt / Tetraalkylammonium salt / Amino acid or derivatives / Carboxylic acid ester / Tertiary amine / Tertiary aliphatic amine
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
quaternary ammonium ion, acetate ester, androstane (CHEBI:9939)

Targets

Kind
Protein
Organism
Human
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. [PubMed:19417616]
  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. [PubMed:18633030]
  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. [PubMed:12145052]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257]
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880]
Kind
Protein
Organism
Human
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. [PubMed:9655875]

Drug created on June 30, 2007 12:08 / Updated on November 12, 2018 07:29