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Showing metabocard for Guanethidine (HMDB0015301)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1)transporters (1) Show 2 proteinsXML
enzymes (1)transporters (1) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:21 UTC
HMDB IDHMDB0015301
Secondary Accession Numbers
  • HMDB15301
Metabolite Identification
Common NameGuanethidine
DescriptionGuanethidine, also known as octadine or ismelin, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Guanethidine is a drug which is used for the treatment of moderate and severe hypertension, either alone or as an adjunct, and for the treatment of renal hypertension. Guanethidine is a very strong basic compound (based on its pKa). Side effects include drowsiness, dizziness, tiredness or confusion. It is a postganglionic sympathetic nerve terminal blocker that prevents the release of norepinephrine from nerve terminals. In contrast to ganglionic blocking agents, Guanethidine suppresses equally the responses mediated by alpha-and beta-adrenergic receptors but does not produce parasympathetic blockade. Guanethidine acts at the sympathetic neuroeffector junction by inhibiting or interfering with the release and/or distribution of norepinephrine (NE), rather than acting at the effector cell by inhibiting the association of norepinephrine with its receptors. This can damage the blood vessels of the brain, heart, and kidneys, resulting in a stroke, heart failure, or kidney failure.
Structure
Data?1582753281
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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 monosulfateHMDB
Guanethidine monosulphateHMDB
Guanethidine sulphaeHMDB
Guanethidine sulfate (1:1)HMDB
Guanethidine sulfate (2:1), 14C-labeledHMDB
OctadineHMDB
OktadinHMDB
monoSulfate, guanethidineHMDB
Guanethidine sulfateHMDB
Guanethidine sulfate (1:2)HMDB
Guanethidine sulfate (2:1)HMDB
IsmelinHMDB
IsobarinHMDB
((2-Hexahydro-1(2H)-azocinyl)ethyl)guanidineHMDB
Sulfate, guanethidineHMDB
Chemical FormulaC10H22N4
Average Molecular Weight198.3085
Monoisotopic Molecular Weight198.184446724
IUPAC Name2-[2-(azocan-1-yl)ethyl]guanidine
Traditional Nameismelin
CAS Registry Number645-43-2
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 KeyACGDKVXYNVEAGU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 °C (sulfate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility2.25 g/LNot Available
LogP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.25 g/LALOGPS
logP0.89ALOGPS
logP0.74ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)11.77ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.64 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.7 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dl-9800000000-92577f077502658eda15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-63bf143534cccc53e099Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000g-3900000000-b0c1213301460e6159e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-8900000000-a1d8b2ab68936ac02c48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-007c-9200000000-091425f6c0c880a5afddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4r-9000000000-3d40142c51842fbbf5fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2900000000-3c0d9ad535e10192de33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pc-9800000000-f1d0a92cd4e7f5d5da78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9200000000-7f351fa76ffff520f407Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-2900000000-85cc5b54f54b4d66b7d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-5456c549767554136a2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-72d038e0b4bab6976722Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01170 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01170 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01170
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3398
KEGG Compound IDC07036
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanethidine
METLIN IDNot Available
PubChem Compound3518
PDB IDNot Available
ChEBI ID5557
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
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

Enzyme Details
1. Sodium-dependent noradrenaline transporter
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 ]