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Identification
NameGuanadrel
Accession NumberDB00226  (APRD01006)
TypeSmall Molecule
GroupsApproved
DescriptionGuanadrel is a postganglionic adrenergic blocking agent. Uptake of guanadrel and storage in sympathetic neurons occurs via the norepinephrine pump or transporter.
Structure
Thumb
Synonyms
Guanadrel
Guanadrelum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnarelCutter
HylorelPennwalt
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Guanadrel sulfate
22195-34-2
Thumb
  • InChI Key: RTEVGQJRTFFMLL-UHFFFAOYSA-N
  • Monoisotopic Mass: 524.262833446
  • Average Mass: 524.63
DBSALT000889
Categories
UNII765C9332T4
CAS number40580-59-4
WeightAverage: 213.2768
Monoisotopic: 213.147726867
Chemical FormulaC10H19N3O2
InChI KeyHPBNRIOWIXYZFK-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine
SMILES
NC(N)=NCC1COC2(CCCCC2)O1
Pharmacology
IndicationUsed to treat and control hypertension.
Structured Indications Not Available
PharmacodynamicsHigh blood pressure adds to the work load of the heart and arteries. If it continues for a long time, the heart and arteries may not function properly. This can damage the blood vessels of the brain, heart, and kidneys resulting in a stroke, heart failure, or kidney failure. High blood pressure may also increase the risk of heart attacks. These problems may be less likely to occur if blood pressure is controlled. Guanadrel works by controlling nerve impulses along certain nerve pathways. As a result, it relaxes the blood vessels so that blood passes through them more easily. This helps to lower blood pressure.
Mechanism of actionGuanadrel is a postganglionic adrenergic blocking agent. Uptake of guanadrel and storage in sympathetic neurons occurs via the norepinephrine pump or transporter. Guanadrel slowly displaces norepinephrine from its storage in nerve endings and thereby blocks the release of norepinephrine normally produced by nerve stimulation. The reduction in neurotransmitter release in response to sympathetic nerve stimulation, as a result of catecholamine depletion, leads to reduced arteriolar vasoconstriction, especially the reflex increase in sympathetic tone that occurs with a change in position.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium-dependent noradrenaline transporterProteinyes
partial agonist
HumanP23975 details
Related Articles
AbsorptionRapidly and readily absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingLow, approximately 20%
Metabolism

Primarily hepatic

Route of eliminationNot Available
Half life10 hours
ClearanceNot Available
ToxicitySide effects include dizziness, drowsiness, headache, constipation, diarrhea, gas pains, loss of appetite, fatigue, and nasal congestion.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Guanadrel.Experimental
AcebutololGuanadrel may increase the hypotensive activities of Acebutolol.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Guanadrel.Approved, Investigational
AliskirenGuanadrel may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololGuanadrel may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AmbrisentanGuanadrel may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineGuanadrel may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineGuanadrel may increase the hypotensive activities of Amlodipine.Approved
AtenololGuanadrel may increase the hypotensive activities of Atenolol.Approved
BenazeprilGuanadrel may increase the hypotensive activities of Benazepril.Approved, Investigational
BendroflumethiazideGuanadrel may increase the hypotensive activities of Bendroflumethiazide.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Guanadrel.Withdrawn
BepridilGuanadrel may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Guanadrel.Approved
BethanidineBethanidine may increase the hypotensive activities of Guanadrel.Approved
BimatoprostGuanadrel may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololGuanadrel may increase the hypotensive activities of Bisoprolol.Approved
BosentanGuanadrel may increase the hypotensive activities of Bosentan.Approved, Investigational
BretyliumGuanadrel may increase the hypotensive activities of Bretylium.Approved
BrimonidineGuanadrel may increase the hypotensive activities of Brimonidine.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Guanadrel.Approved
BupranololGuanadrel may increase the hypotensive activities of Bupranolol.Approved
CandesartanGuanadrel may increase the hypotensive activities of Candesartan.Approved
CandoxatrilGuanadrel may increase the hypotensive activities of Candoxatril.Experimental
CaptoprilGuanadrel may increase the hypotensive activities of Captopril.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Guanadrel.Withdrawn
CarteololGuanadrel may increase the hypotensive activities of Carteolol.Approved
CarvedilolGuanadrel may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololGuanadrel may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideGuanadrel may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneGuanadrel may increase the hypotensive activities of Chlorthalidone.Approved
CilazaprilGuanadrel may increase the hypotensive activities of Cilazapril.Approved
ClonidineGuanadrel may increase the hypotensive activities of Clonidine.Approved
CryptenamineGuanadrel may increase the hypotensive activities of Cryptenamine.Approved
CyclothiazideGuanadrel may increase the hypotensive activities of Cyclothiazide.Approved
DebrisoquinGuanadrel may increase the hypotensive activities of Debrisoquin.Approved
DeserpidineGuanadrel may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Guanadrel.Approved
DihydralazineGuanadrel may increase the hypotensive activities of Dihydralazine.Investigational
DiltiazemGuanadrel may increase the hypotensive activities of Diltiazem.Approved
DorzolamideGuanadrel may increase the hypotensive activities of Dorzolamide.Approved
DoxazosinGuanadrel may increase the hypotensive activities of Doxazosin.Approved
EfonidipineGuanadrel may increase the hypotensive activities of Efonidipine.Approved
EnalaprilGuanadrel may increase the hypotensive activities of Enalapril.Approved, Vet Approved
EnalaprilatGuanadrel may increase the hypotensive activities of Enalaprilat.Approved
EpoprostenolGuanadrel may increase the hypotensive activities of Epoprostenol.Approved
EprosartanGuanadrel may increase the hypotensive activities of Eprosartan.Approved
FelodipineGuanadrel may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamGuanadrel may increase the hypotensive activities of Fenoldopam.Approved
FosinoprilGuanadrel may increase the hypotensive activities of Fosinopril.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Guanadrel.Approved, Vet Approved
GuanabenzGuanadrel may increase the hypotensive activities of Guanabenz.Approved
GuanethidineGuanadrel may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanadrel may increase the hypotensive activities of Guanfacine.Approved, Investigational
HexamethoniumGuanadrel may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Guanadrel.Approved
HydralazineGuanadrel may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideGuanadrel may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideGuanadrel may increase the hypotensive activities of Hydroflumethiazide.Approved
IloprostIloprost may increase the hypotensive activities of Guanadrel.Approved, Investigational
ImidaprilGuanadrel may increase the hypotensive activities of Imidapril.Investigational
IndapamideGuanadrel may increase the hypotensive activities of Indapamide.Approved
IndenololGuanadrel may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminGuanadrel may increase the hypotensive activities of Indoramin.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Guanadrel.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Guanadrel.Withdrawn
IrbesartanGuanadrel may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Guanadrel.Approved
IsradipineGuanadrel may increase the hypotensive activities of Isradipine.Approved
KetanserinGuanadrel may increase the hypotensive activities of Ketanserin.Investigational
LabetalolGuanadrel may increase the hypotensive activities of Labetalol.Approved
LacidipineGuanadrel may increase the hypotensive activities of Lacidipine.Approved
LatanoprostGuanadrel may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineGuanadrel may increase the hypotensive activities of Lercanidipine.Approved, Investigational
LisinoprilGuanadrel may increase the hypotensive activities of Lisinopril.Approved, Investigational
LofexidineGuanadrel may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanGuanadrel may increase the hypotensive activities of Losartan.Approved
MacitentanGuanadrel may increase the hypotensive activities of Macitentan.Approved
ManidipineGuanadrel may increase the hypotensive activities of Manidipine.Approved
MebanazineMebanazine may increase the hypotensive activities of Guanadrel.Withdrawn
MecamylamineGuanadrel may increase the hypotensive activities of Mecamylamine.Approved
MethyldopaGuanadrel may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Guanadrel.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Guanadrel.Approved, Investigational
MetipranololGuanadrel may increase the hypotensive activities of Metipranolol.Approved
MetolazoneGuanadrel may increase the hypotensive activities of Metolazone.Approved
MetoprololGuanadrel may increase the hypotensive activities of Metoprolol.Approved, Investigational
MetyrosineGuanadrel may increase the hypotensive activities of Metyrosine.Approved
MibefradilGuanadrel may increase the hypotensive activities of Mibefradil.Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Guanadrel.Approved
MinoxidilGuanadrel may increase the hypotensive activities of Minoxidil.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Guanadrel.Approved
MoexiprilGuanadrel may increase the hypotensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Guanadrel.Approved
MoxonidineGuanadrel may increase the hypotensive activities of Moxonidine.Approved
NadololGuanadrel may increase the hypotensive activities of Nadolol.Approved
NaftopidilGuanadrel may increase the hypotensive activities of Naftopidil.Investigational
NebivololGuanadrel may increase the hypotensive activities of Nebivolol.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Guanadrel.Withdrawn
NicardipineGuanadrel may increase the hypotensive activities of Nicardipine.Approved
NicorandilGuanadrel may increase the hypotensive activities of Nicorandil.Approved
NiguldipineGuanadrel may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineGuanadrel may increase the hypotensive activities of Nilvadipine.Approved
NimodipineGuanadrel may increase the hypotensive activities of Nimodipine.Approved
NisoldipineGuanadrel may increase the hypotensive activities of Nisoldipine.Approved
NitrendipineGuanadrel may increase the hypotensive activities of Nitrendipine.Approved
NitroprussideGuanadrel may increase the hypotensive activities of Nitroprusside.Approved
ObinutuzumabGuanadrel may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Guanadrel.Withdrawn
OlmesartanGuanadrel may increase the hypotensive activities of Olmesartan.Approved, Investigational
OmapatrilatGuanadrel may increase the hypotensive activities of Omapatrilat.Investigational
OxprenololGuanadrel may increase the hypotensive activities of Oxprenolol.Approved
PargylinePargyline may increase the hypotensive activities of Guanadrel.Approved
PenbutololGuanadrel may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumGuanadrel may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Guanadrel.Approved, Investigational
PerindoprilGuanadrel may increase the hypotensive activities of Perindopril.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Guanadrel.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Guanadrel.Withdrawn
PhenoxybenzamineGuanadrel may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Guanadrel.Withdrawn
PhentolamineGuanadrel may increase the hypotensive activities of Phentolamine.Approved
PinacidilGuanadrel may increase the hypotensive activities of Pinacidil.Withdrawn
PindololGuanadrel may increase the hypotensive activities of Pindolol.Approved
PirlindolePirlindole may increase the hypotensive activities of Guanadrel.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Guanadrel.Withdrawn
PolythiazideGuanadrel may increase the hypotensive activities of Polythiazide.Approved
PrazosinGuanadrel may increase the hypotensive activities of Prazosin.Approved
PropranololGuanadrel may increase the hypotensive activities of Propranolol.Approved, Investigational
QuinaprilGuanadrel may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Guanadrel.Approved
RamiprilRamipril may increase the hypotensive activities of Guanadrel.Approved
RasagilineRasagiline may increase the hypotensive activities of Guanadrel.Approved
RemikirenRemikiren may increase the hypotensive activities of Guanadrel.Approved
RescinnamineGuanadrel may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Guanadrel.Approved
RilmenidineGuanadrel may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatGuanadrel may increase the hypotensive activities of Riociguat.Approved
RituximabGuanadrel may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Guanadrel.Withdrawn
SaprisartanGuanadrel may increase the hypotensive activities of Saprisartan.Experimental
SelegilineSelegiline may increase the hypotensive activities of Guanadrel.Approved, Investigational, Vet Approved
SelexipagGuanadrel may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Guanadrel.Approved, Investigational
SitaxentanGuanadrel may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilGuanadrel may increase the hypotensive activities of Spirapril.Approved
TadalafilTadalafil may increase the antihypertensive activities of Guanadrel.Approved, Investigational
TelmisartanGuanadrel may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilGuanadrel may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinGuanadrel may increase the hypotensive activities of Terlipressin.Approved, Investigational
TiboloneGuanadrel may increase the hypotensive activities of Tibolone.Approved
TicrynafenGuanadrel may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololGuanadrel may increase the hypotensive activities of Timolol.Approved
TolazolineGuanadrel may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
ToloxatoneToloxatone may increase the hypotensive activities of Guanadrel.Approved
TorasemideTorasemide may increase the hypotensive activities of Guanadrel.Approved
TrandolaprilGuanadrel may increase the hypotensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Guanadrel.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Guanadrel.Approved
TravoprostGuanadrel may increase the hypotensive activities of Travoprost.Approved
TreprostinilGuanadrel may increase the hypotensive activities of Treprostinil.Approved, Investigational
TrichlormethiazideGuanadrel may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinGuanadrel may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanGuanadrel may increase the hypotensive activities of Trimethaphan.Approved
UdenafilUdenafil may increase the antihypertensive activities of Guanadrel.Approved, Investigational
UnoprostoneGuanadrel may increase the hypotensive activities of Unoprostone.Approved
ValsartanValsartan may increase the hypotensive activities of Guanadrel.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Guanadrel.Approved
VinpocetineGuanadrel may increase the hypotensive activities of Vinpocetine.Investigational
XylometazolineGuanadrel may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Guanadrel.Approved, Vet Approved
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 3,547,951.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8727
Blood Brain Barrier+0.5276
Caco-2 permeable-0.5409
P-glycoprotein substrateNon-substrate0.6176
P-glycoprotein inhibitor INon-inhibitor0.9348
P-glycoprotein inhibitor IINon-inhibitor0.8788
Renal organic cation transporterNon-inhibitor0.5077
CYP450 2C9 substrateNon-substrate0.8797
CYP450 2D6 substrateNon-substrate0.6273
CYP450 3A4 substrateNon-substrate0.7651
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9529
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.584
CarcinogenicityNon-carcinogens0.9459
BiodegradationNot ready biodegradable0.9371
Rat acute toxicity2.4799 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8914
hERG inhibition (predictor II)Non-inhibitor0.8892
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Pharmaceutical Utilization Management Program VA Inc.
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point213.5-215U.S. Patent 3,547,951.
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.93 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.54 m3·mol-1ChemAxon
Polarizability23.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,3-dioxolanes. These are organic compounds containing 1,3-dioxolane, an aliphatic five-member ring with two oxygen atoms in ring positions 1 and 3.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxolanes
Sub Class1,3-dioxolanes
Direct Parent1,3-dioxolanes
Alternative Parents
Substituents
  • Meta-dioxolane
  • Guanidine
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
partial agonist
General Function:
Norepinephrine: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 Da
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23