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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014371
Secondary Accession Numbers
  • HMDB14371
Metabolite Identification
Common NameGuanadrel
DescriptionGuanadrel is a postganglionic sympathetic adrenergic antagonist that is administered orally to treat hypertension (high blood pressure). It was used in the form of its sulfate (trade name: Hylorel) but has been largely superseded by other antihypertensive agents due to its unpleasant side effect of orthostatic hypotension (i.e. dizziness when standing) (PMID: 6143629 ). Guanadrel both prevents noradrenaline (norepinephrine) release and depletes noradrenaline stores which effectively creates a peripheral sympathetic blockade. This serves to reduce vasoconstriction which subsequently lowers blood pressure (PMID: 3896742 ).
Structure
Data?1582753171
Synonyms
ValueSource
GuanadrelumChEBI
HylorelKegg
Guanadrel sulfuric acidHMDB
Guanadrel sulphateHMDB
Guanadrel sulphuric acidHMDB
N-(1,4-Dioxaspiro[4.5]dec-2-ylmethyl)guanidineHMDB
Guanadrel monosulfateHMDB
Guanadrel monosulphateHMDB
Guanadrel sulfateHMDB
GuanadrelHMDB
Chemical FormulaC10H19N3O2
Average Molecular Weight213.2768
Monoisotopic Molecular Weight213.147726867
IUPAC Name2-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine
Traditional Nameguanadrel
CAS Registry Number40580-59-4
SMILES
NC(N)=NCC1COC2(CCCCC2)O1
InChI Identifier
InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)
InChI KeyHPBNRIOWIXYZFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentKetals
Alternative Parents
Substituents
  • Ketal
  • Meta-dioxolane
  • Guanidine
  • Oxacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.93 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.93 g/LALOGPS
logP0.03ALOGPS
logP0.62ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.85ChemAxon
pKa (Strongest Basic)12.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.54 m³·mol⁻¹ChemAxon
Polarizability23.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.77331661259
DarkChem[M-H]-144.76231661259
DeepCCS[M+H]+150.45330932474
DeepCCS[M-H]-148.09530932474
DeepCCS[M-2H]-183.18430932474
DeepCCS[M+Na]+157.83730932474
AllCCS[M+H]+149.532859911
AllCCS[M+H-H2O]+145.732859911
AllCCS[M+NH4]+153.032859911
AllCCS[M+Na]+154.032859911
AllCCS[M-H]-151.532859911
AllCCS[M+Na-2H]-151.932859911
AllCCS[M+HCOO]-152.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GuanadrelNC(N)=NCC1COC2(CCCCC2)O12374.3Standard polar33892256
GuanadrelNC(N)=NCC1COC2(CCCCC2)O11675.7Standard non polar33892256
GuanadrelNC(N)=NCC1COC2(CCCCC2)O11986.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guanadrel,1TMS,isomer #1C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O12007.3Semi standard non polar33892256
Guanadrel,1TMS,isomer #1C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O11792.2Standard non polar33892256
Guanadrel,1TMS,isomer #1C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O13035.7Standard polar33892256
Guanadrel,2TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C2162.5Semi standard non polar33892256
Guanadrel,2TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C1842.2Standard non polar33892256
Guanadrel,2TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C3058.8Standard polar33892256
Guanadrel,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C2115.8Semi standard non polar33892256
Guanadrel,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C1997.0Standard non polar33892256
Guanadrel,2TMS,isomer #2C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C3156.9Standard polar33892256
Guanadrel,3TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C2187.2Semi standard non polar33892256
Guanadrel,3TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C2056.1Standard non polar33892256
Guanadrel,3TMS,isomer #1C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C2941.9Standard polar33892256
Guanadrel,4TMS,isomer #1C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2234.8Semi standard non polar33892256
Guanadrel,4TMS,isomer #1C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2283.6Standard non polar33892256
Guanadrel,4TMS,isomer #1C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2731.2Standard polar33892256
Guanadrel,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O12235.4Semi standard non polar33892256
Guanadrel,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O12042.6Standard non polar33892256
Guanadrel,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O13280.1Standard polar33892256
Guanadrel,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C2571.1Semi standard non polar33892256
Guanadrel,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C2294.2Standard non polar33892256
Guanadrel,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C3251.5Standard polar33892256
Guanadrel,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C2516.9Semi standard non polar33892256
Guanadrel,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C2436.6Standard non polar33892256
Guanadrel,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C3416.7Standard polar33892256
Guanadrel,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2794.0Semi standard non polar33892256
Guanadrel,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2704.2Standard non polar33892256
Guanadrel,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3126.5Standard polar33892256
Guanadrel,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3074.0Semi standard non polar33892256
Guanadrel,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3053.4Standard non polar33892256
Guanadrel,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2977.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-3e328dd7598b02063d5a2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 10V, Positive-QTOFsplash10-03di-4490000000-a78d2d502660f357a4912017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 20V, Positive-QTOFsplash10-0229-9310000000-0778ebe61728471eea0d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 40V, Positive-QTOFsplash10-03dl-9000000000-a1a36d3de5660c0018f72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 10V, Negative-QTOFsplash10-0229-9760000000-08de942fb4b119d03f152017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 20V, Negative-QTOFsplash10-052f-9100000000-11ed2297e33929803cf02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 40V, Negative-QTOFsplash10-052f-9000000000-7f78b604a8c1fcc8116a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 10V, Positive-QTOFsplash10-03di-0290000000-dbf1037b6bac01f25ea62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 20V, Positive-QTOFsplash10-08gj-9720000000-546065e239736f71a0882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 40V, Positive-QTOFsplash10-0536-9200000000-02d4464b6a16c151c7ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 10V, Negative-QTOFsplash10-044i-1960000000-1210a29f67ee4cc69b4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 20V, Negative-QTOFsplash10-014j-8900000000-69e4c1bbae3fa476a53c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanadrel 40V, Negative-QTOFsplash10-0006-9400000000-18678395b551c1f8c3d42021-09-23Wishart LabView Spectrum
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 DB00226 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00226 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00226
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID35305
KEGG Compound IDC07035
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanadrel
METLIN IDNot Available
PubChem Compound38521
PDB IDNot Available
ChEBI ID5555
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. [PubMed:3896742 ]
  2. Cressman MD, Vidt DG: Newer agents in the treatment of arterial hypertension. Cleve Clin Q. 1984 Spring;51(1):179-84. [PubMed:6143629 ]

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Malinow SH: Comparison of guanadrel and guanethidine efficacy and side effects. Clin Ther. 1983;5(3):284-9. [PubMed:6850722 ]
  4. Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. [PubMed:3896742 ]
  5. Palmer JD, Nugent CA: Guanadrel sulfate: a postganglionic sympathetic inhibitor for the treatment of mild to moderate hypertension. Pharmacotherapy. 1983 Jul-Aug;3(4):220-9. [PubMed:6351026 ]