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Guanethidine

July 24, 2017
Common Name

Guanethidine Description

An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues. [PubChem] Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (2-(octahydro-1-Azocinyl)ethyl)guanidineChEBI 2-(1'-Azacyclooctyl)ethylguanidineChEBI 2-(1-N,N-heptamethyleneimino)EthylguanidineChEBI GuanethidinumChEBI GuanetidinaChEBI N-(2-Perhydroazocin-1-ylethyl)guanidineChEBI Guanethidine monoslifateHMDB Guanethidine monosliphateHMDB Guanethidine sliphaeHMDB Guanethidine slifate (1:1)MeSH Guanethidine slifate (2:1), 14C-labeledMeSH OctadineMeSH OktadinMeSH Monoslifate, guanethidineMeSH Guanethidine slifateMeSH Guanethidine slifate (1:2)MeSH Guanethidine slifate (2:1)MeSH IsmelinMeSH IsobarinMeSH ((2-hexahydro-1(2H)-Azocinyl)ethyl)guanidineMeSH Slifate, guanethidineMeSH

Chemical Formlia

C10H22N4 Average Molecliar Weight

198.3085 Monoisotopic Molecliar Weight

198.184446724 IUPAC Name

2-[2-(azocan-1-yl)ethyl]guanidine Traditional Name

ismelin CAS Registry Number

645-43-2 SMILES

NC(N)=NCCN1CCCCCCC1

InChI Identifier

InChI=1S/C10H22N4/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14/h1-9H2,(H4,11,12,13)

InChI Key

ACGDKVXYNVEAGU-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic nitrogen compounds Sub Class

Organonitrogen compounds Direct Parent

Guanidines Alternative Parents

  • Trialkylamines
  • Carboximidamides
  • Azacyclic compounds
  • Organopnictogen compounds
  • Imines
  • Hydrocarbon derivatives

    • Substituents

  • Tertiary aliphatic amine
  • Tertiary amine
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Amine
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • guanidines (CHEBI:5557 )
  • azocanes (CHEBI:5557 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic Agents
  • Antihypertensive Agents
  • Sympatholytics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point250 °C (slifate salt)Not Available Boiling PointNot AvailableNot Available Water Solubility2.25e+00 g/LNot Available LogP0.8Not Available

    Predicted Properties

    Property Value Source Water Solubility2.25 mg/mLALOGPS logP0.89ALOGPS logP0.74ChemAxon logS-1.9ALOGPS pKa (Strongest Basic)11.77ChemAxon Physiological Charge2ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area67.64 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity59.7 m3·mol-1ChemAxon Polarizability23.67 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0002-0900000000-63bf143534cccc53e099View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-000g-3900000000-b0c1213301460e6159e2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-000f-8900000000-a1d8b2ab68936ac02c48View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-007c-9200000000-091425f6c0c880a5afddView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0a4r-9000000000-3d40142c51842fbbf5fcView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • 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 DB01170

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01170

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01170 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

    3398 KEGG Compound ID

    C07036 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Guanethidine NuGOwiki Link

    HMDB15301 Metagene Link

    HMDB15301 METLIN ID

    Not Available PubChem Compound

    3518 PDB ID

    Not Available ChEBI ID

    5557

    Product: ADPS

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

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    Transporters

    General function:
    Involved in neurotransmitter:sodium symporter activity
    Specific function:
    Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
    Gene Name:
    SLC6A2
    Uniprot ID:
    P23975
    Molecular weight:
    69331.42
    References
    1. Joyce PI, Atcheson R, Marcus RJ, Heffernan AM, Rowbotham DJ, Lambert DG: Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. Neurosci Lett. 2001 Jun 15;305(3):161-4. [PubMed:11403930 ]
    2. Yi E, Love JA: Alpha-adrenergic modulation of synaptic transmission in rabbit pancreatic ganglia. Auton Neurosci. 2005 Oct 30;122(1-2):45-57. Epub 2005 Aug 25. [PubMed:16126010 ]
    3. Galli A, Blakely RD, DeFelice LJ: Norepinephrine transporters have channel modes of conduction. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8671-6. [PubMed:8710929 ]

    PMID: 19784811

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