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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
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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[8.7.0.0^{2,7}.0^{11,15}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassSteroid Esters
Direct parentSteroid Esters
Alternative parentsAndrogens and Derivatives; Piperidines; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Ethers
Substituentspiperidine; tertiary amine; carboxylic acid ester; enolate; ether; carboxylic acid derivative; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the steroid esters. These are compounds containing a steroid moeity which bears a carboxylic acid ester group.
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
Property Value Probability
Human Intestinal Absorption - 0.8913
Blood Brain Barrier + 0.878
Caco-2 permeable + 0.5457
P-glycoprotein substrate Substrate 0.77
P-glycoprotein inhibitor I Inhibitor 0.6962
P-glycoprotein inhibitor II Inhibitor 0.6508
Renal organic cation transporter Non-inhibitor 0.6862
CYP450 2C9 substrate Non-substrate 0.8382
CYP450 2D6 substrate Non-substrate 0.7638
CYP450 3A4 substrate Substrate 0.742
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9229
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9368
Ames test Non AMES toxic 0.7499
Carcinogenicity Non-carcinogens 0.9265
Biodegradation Not ready biodegradable 0.8557
Rat acute toxicity 2.6653 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9021
hERG inhibition (predictor II) Non-inhibitor 0.7784
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionIntravenous
Prices
Unit descriptionCostUnit
Vecuronium 20 mg vial5.05USDvial
Vecuronium 10 mg vial3.64USDvial
Vecuronium 10 mg/10 ml syringe2.36USDml
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 g/lALOGPS
logP2.07ALOGPS
logP0.89ChemAxon
logS-7.5ALOGPS
pKa (strongest basic)9.65ChemAxon
physiological charge2ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area55.84ChemAxon
rotatable bond count6ChemAxon
refractivity169.31ChemAxon
polarizability66.85ChemAxon
number of rings6ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
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
ResourceLink
KEGG CompoundC07553
PubChem Compound39765
PubChem Substance46507656
ChemSpider36357
ChEBI9939
ChEMBLCHEMBL1201219
Therapeutic Targets DatabaseDAP000354
PharmGKBPA164748865
IUPHAR4002
Guide to Pharmacology4002
Drug Product Database687405
Drugs.comhttp://www.drugs.com/cdi/vecuronium.html
WikipediaVecuronium
ATC CodesM03AC03
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmikacinThe agent increases the effect of muscle relaxant
AminophyllineTheophylline decreases the effect of muscle relaxant
AzathioprineThe agent decreases the effect of the muscle relaxant
BetamethasoneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Betamethasone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
CarbamazepineDecreases the effect of muscle relaxant
ClindamycinThe agent increases the effect of muscle relaxant
ColistimethateColistimethate may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Consider alternate therapy or monitor for prolonged neuromuscular blocking effects, such as respiratory paralysis.
CorticotropinVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Corticotropin. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
Cortisone acetateVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Cortisone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
DexamethasoneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Dexamethasone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
FludrocortisoneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Fludrocortisone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
FosphenytoinPhenytoin decreases the effect of muscle relaxant
GentamicinThe agent increases the effect of muscle relaxant
HydrocortisoneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Hydrocortisone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
LincomycinThe agent increases the effect of muscle relaxant
MercaptopurineThe agent dereases the effect of the muscle relaxant
MethylprednisoloneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Methylprednisolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
NetilmicinThe agent increases the effect of muscle relaxant
OxtriphyllineTheophylline decreases the effect of muscle relaxant
PhenytoinPhenytoin decreases the effect of the muscle relaxant
PiperacillinThe agent increases the effect of the muscle relaxant
Polymyxin B SulfatePolymyxin B may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Consider alternate therapy or monitor for prolonged neuromuscular blocking effects, such as respiratory paralysis.
PrednisoloneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Prednisolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
PrednisoneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Prednisone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
QuinidineThe quinine derivative increases the effect of the muscle relaxant
QuinineQuinine may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Concurrent therapy should be avoided.
TheophyllineTheophylline decreases the effect of the muscle relaxant
TobramycinThe agent increases the effect of the muscle relaxant
TriamcinoloneVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Triamcinolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
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