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Identification
NameVecuronium
Accession NumberDB01339
TypeSmall Molecule
GroupsApproved
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. [PubChem]

Structure
Thumb
Synonyms
Vecuronium
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Norcuron Inj 10mg/vialpowder for solution10 mgintravenousOrganon Canada Ltd Ltee1986-12-312009-08-04Canada
Vecuronium Bromide for Injectionpowder for solution10.00 mgintravenousHospira Healthcare Corporation2000-06-01Not applicableCanada
Vecuronium Bromide for Injectionpowder for solution10 mgintravenousPharmaceutical Partners Of Canada Inc2000-06-132008-02-15Canada
Vecuronium Bromide for Injectionpowder for solution20.00 mgintravenousHospira Healthcare Corporation2000-01-28Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vecuroniuminjection, powder, lyophilized, for solution20 mg/20mLintravenousSagent Pharmaceuticals2011-08-012016-04-05Us
Vecuroniuminjection, powder, lyophilized, for solution10 mg/10mLintravenousSagent Pharmaceuticals2011-08-012016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousREMEDYREPACK INC.2015-06-232016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-112016-04-23Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousMylan Institutional LLC2011-05-112016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousCardinal Health2009-07-212016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution10 mg/10mLintravenousCardinal Health1999-08-252016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousAkorn Strides Llc2010-09-152016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousCardinal Health2000-08-012016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution20 mg/20mLintravenousTeva Parenteral Medicines, Inc.2002-11-142016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousSun Pharma Global FZE2014-12-152016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution10 mg/10mLintravenousTeva Parenteral Medicines, Inc.2002-11-142016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousSun Pharma Global FZE2014-12-152016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousHospira, Inc.1999-10-212016-04-23Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousMylan Institutional LLC2011-05-112016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousHospira, Inc.1999-10-212016-04-23Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousMylan Institutional LLC2011-05-112016-04-05Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-112016-04-23Us
Vecuronium Bromideinjection, powder, lyophilized, for solution1 mg/mLintravenousMylan Institutional LLC2011-05-112016-04-05Us
Vecuronium Bromide for Injectioninjection, powder, lyophilized, for solution1 mg/mLintravenousSun Pharma Global Inc.2009-07-212016-04-05Us
Vecuronium Bromide for Injectioninjection, powder, lyophilized, for solution1 mg/mLintravenousSun Pharma Global Inc.2009-07-212016-04-05Us
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Vecuronium bromide
50700-72-6
Thumb
  • InChI Key: VEPSYABRBFXYIB-PWXDFCLTSA-M
  • Monoisotopic Mass: 636.350171
  • Average Mass: 637.744
DBSALT001200
Categories
UNII5438723848
CAS number86029-43-8
WeightAverage: 557.8274
Monoisotopic: 557.431833322
Chemical FormulaC34H57N2O4
InChI KeyInChIKey=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]([[email protected]](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[[email protected]](OC(C)=O)[[email protected]](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Cyclohexylamine
  • Piperidine
  • Acetate salt
  • Quaternary ammonium salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationVecuronium is a muscle relaxing agent and is used as an ajunct in general anesthesia.
PharmacodynamicsVecuronium 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 actionVecuronium 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

100%

Route of eliminationFecal (40-75%) and renal (30% as unchanged drug and metabolites)
Half life51–80 minutes
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionintravenous1 mg/mL
Injection, powder, lyophilized, for solutionintravenous10 mg/10mL
Injection, powder, lyophilized, for solutionintravenous20 mg/20mL
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point228 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesM03AC03
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmikacinAmikacin may increase the activities of Vecuronium.
AmlodipineAmlodipine may increase the neuromuscular blocking activities of Vecuronium.
AmrinoneAmrinone may increase the neuromuscular blocking activities of Vecuronium.
ArbekacinArbekacin may increase the activities of Vecuronium.
BepridilBepridil may increase the neuromuscular blocking activities of Vecuronium.
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Vecuronium.
Botulinum Toxin Type BVecuronium may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Vecuronium.
CarbamazepineThe serum concentration of Vecuronium can be decreased when it is combined with Carbamazepine.
ClindamycinClindamycin may increase the neuromuscular blocking activities of Vecuronium.
ColistimethateColistimethate may increase the neuromuscular blocking activities of Vecuronium.
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Vecuronium.
DantroleneDantrolene may increase the neuromuscular blocking activities of Vecuronium.
DigoxinVecuronium may increase the arrhythmogenic activities of Digoxin.
FelodipineFelodipine may increase the neuromuscular blocking activities of Vecuronium.
FludrocortisoneVecuronium may increase the adverse neuromuscular activities of Fludrocortisone.
FlunarizineFlunarizine may increase the neuromuscular blocking activities of Vecuronium.
FramycetinFramycetin may increase the activities of Vecuronium.
GabapentinGabapentin may increase the neuromuscular blocking activities of Vecuronium.
GentamicinGentamicin may increase the activities of Vecuronium.
IsofluraneIsoflurane may increase the neuromuscular blocking activities of Vecuronium.
IsradipineIsradipine may increase the neuromuscular blocking activities of Vecuronium.
KanamycinKanamycin may increase the activities of Vecuronium.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Vecuronium.
LamotrigineLamotrigine may increase the neuromuscular blocking activities of Vecuronium.
LercanidipineLercanidipine may increase the neuromuscular blocking activities of Vecuronium.
LincomycinLincomycin may increase the neuromuscular blocking activities of Vecuronium.
LithiumLithium may increase the neuromuscular blocking activities of Vecuronium.
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Vecuronium.
MinocyclineMinocycline may increase the neuromuscular blocking activities of Vecuronium.
NeomycinNeomycin may increase the activities of Vecuronium.
NetilmicinNetilmicin may increase the activities of Vecuronium.
NicardipineNicardipine may increase the neuromuscular blocking activities of Vecuronium.
NimodipineNimodipine may increase the neuromuscular blocking activities of Vecuronium.
NisoldipineNisoldipine may increase the neuromuscular blocking activities of Vecuronium.
NitrendipineNitrendipine may increase the neuromuscular blocking activities of Vecuronium.
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Vecuronium.
PerhexilinePerhexiline may increase the neuromuscular blocking activities of Vecuronium.
PhenytoinPhenytoin may decrease the neuromuscular blocking activities of Vecuronium.
PiperacillinPiperacillin may increase the neuromuscular blocking activities of Vecuronium.
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Vecuronium.
PrenylaminePrenylamine may increase the neuromuscular blocking activities of Vecuronium.
ProcainamideProcainamide may increase the neuromuscular blocking activities of Vecuronium.
QuinidineQuinidine may increase the neuromuscular blocking activities of Vecuronium.
QuinineQuinine may increase the neuromuscular blocking activities of Vecuronium.
RibostamycinRibostamycin may increase the activities of Vecuronium.
RisedronateRisedronate may increase the neuromuscular blocking activities of Vecuronium.
SpectinomycinSpectinomycin may increase the activities of Vecuronium.
SpironolactoneSpironolactone may increase the neuromuscular blocking activities of Vecuronium.
StreptomycinStreptomycin may increase the activities of Vecuronium.
TacrineTacrine may decrease the neuromuscular blocking activities of Vecuronium.
TobramycinTobramycin may increase the activities of Vecuronium.
TorasemideTorasemide may decrease the neuromuscular blocking activities of Vecuronium.
VancomycinVancomycin may increase the neuromuscular blocking activities of Vecuronium.
VerapamilVerapamil may increase the neuromuscular blocking activities of Vecuronium.
Food InteractionsNot Available

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
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-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
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
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 ]
Comments
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Drug created on June 30, 2007 12:08 / Updated on April 29, 2016 21:21