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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
SynonymLanguageCode
SID50112721Not AvailableNot Available
VecuroniumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vecuroniuminjection, powder, lyophilized, for solution10 mg/10mLintravenousSagent Pharmaceuticals2011-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vecuroniuminjection, powder, lyophilized, for solution20 mg/20mLintravenousSagent Pharmaceuticals2011-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number50700-72-6
WeightAverage: 557.8274
Monoisotopic: 557.431833322
Chemical FormulaC34H57N2O4
InChI KeyBGSZAXLLHYERSY-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
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.
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 substrateNon-inhibitor0.9229
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionintravenous10 mg/10mL
Injection, powder, lyophilized, for solutionintravenous20 mg/20mL
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 ReferenceNot Available
External Links
ATC CodesM03AC03
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmikacinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
AmlodipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
AmrinoneMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
ArbekacinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
BepridilMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
CapreomycinMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
CarbamazepineCarBAMazepine may decrease the serum concentration of Vecuronium.
ColistimethateMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
DantroleneDantrolene may enhance the neuromuscular-blocking effect of Vecuronium.
FelodipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
FlunarizineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
FramycetinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
GabapentinMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
GentamicinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
IsradipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
KanamycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
LamotrigineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
LercanidipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
LithiumMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
Magnesium SulfateMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
NeomycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
NetilmicinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
NicardipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
NimodipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
NisoldipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
NitrendipineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
PerhexilineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
PiperacillinPiperacillin may enhance the neuromuscular-blocking effect of Vecuronium.
PrenylamineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
ProcainamideMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
QuinidineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
QuinineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
RibostamycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
RisedronateMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
SpectinomycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
SpironolactoneMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
StreptomycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
TobramycinMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
VancomycinMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
VerapamilMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents (Nondepolarizing).
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

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. Pubmed
  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. Pubmed
  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

Transporters

1. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

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
  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

2. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

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Drug created on June 30, 2007 12:08 / Updated on September 16, 2013 17:14