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Vecuronium

July 24, 2017
Common Name

Vecuronium Description

Monoquaternary homolog of pancuronium. A non-depolarizing neuromuscliar blocking agent with shorter duration of action than pancuronium. Its lack of significant cardiovascliar 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 neuromuscliar blocking agents. [PubChem] Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Maleate, vecuroniumMeSH NC 45MeSH NorcuronMeSH ORG-NC 45MeSH ORGNC45MeSH Vecuronium bromideMeSH Vecuronium hydrobromideMeSH Bromide, vecuroniumMeSH Citrate, vecuroniumMeSH ORG NC 45MeSH ORG NC45MeSH ORG-NC45MeSH ORGNC 45MeSH Vecuronium bromide, quaternary ionMeSH Vecuronium citrateMeSH Vecuronium hydrochlorideMeSH Vecuronium phosphateMeSH Hydrobromide, vecuroniumMeSH Hydrochloride, vecuroniumMeSH NC-45MeSH ORG-NC-45MeSH Phosphate, vecuroniumMeSH Vecuronium maleateMeSH

Chemical Formlia

C34H57N2O4 Average Molecliar Weight

557.8274 Monoisotopic Molecliar Weight

557.431833322 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 Traditional Name

vecuronium CAS Registry Number

50700-72-6 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

InChI Identifier

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

InChI Key

BGSZAXLLHYERSY-XQIGCQGXSA-N Chemical 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 moleclies 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
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organic cations

    • 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
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic salt
  • Organic cation
  • Aliphatic heteropolycyclic compound

    • Molecliar Framework

    Aliphatic heteropolycyclic compounds External Descriptors

  • quaternary ammonium ion (CHEBI:9939 )
  • acetate ester (CHEBI:9939 )
  • androstane (CHEBI:9939 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Neuromuscliar Nondepolarizing Agents
  • Nicotinic Antagonists

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.86e-05 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01339

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01339

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01339 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    36358 KEGG Compound ID

    C07553 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Vecuronium NuGOwiki Link

    HMDB15432 Metagene Link

    HMDB15432 METLIN ID

    Not Available PubChem Compound

    39765 PDB ID

    Not Available ChEBI ID

    9939

    Product: Triclabendazole

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in extracellular ligand-gated ion channel activity
    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:
    59764.8
    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

    General function:
    Involved in ATP binding
    Specific function:
    Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
    Gene Name:
    ABCB1
    Uniprot ID:
    P08183
    Molecular weight:
    141477.3
    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 ]
    General function:
    Involved in ion 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, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
    Gene Name:
    SLC22A1
    Uniprot ID:
    O15245
    Molecular weight:
    61187.4
    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 ]

    PMID: 19075016

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