Identification

Name
Guanadrel
Accession Number
DB00226  (APRD01006)
Type
Small Molecule
Groups
Approved
Description

Guanadrel 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
Product Ingredients
IngredientUNIICASInChI Key
Guanadrel sulfateMT147RMO9122195-34-2RTEVGQJRTFFMLL-UHFFFAOYSA-N
International/Other Brands
Anarel (Cutter) / Hylorel (Pennwalt)
Categories
UNII
765C9332T4
CAS number
40580-59-4
Weight
Average: 213.2768
Monoisotopic: 213.147726867
Chemical Formula
C10H19N3O2
InChI Key
HPBNRIOWIXYZFK-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

Indication

Used to treat and control hypertension.

Pharmacodynamics

High 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 action

Guanadrel 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.

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
partial agonist
Human
Absorption

Rapidly and readily absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

Low, approximately 20%

Metabolism

Primarily hepatic

Route of elimination
Not Available
Half life

10 hours

Clearance
Not Available
Toxicity

Side effects include dizziness, drowsiness, headache, constipation, diarrhea, gas pains, loss of appetite, fatigue, and nasal congestion.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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, Investigational
AcemetacinThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
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
AmphetamineAmphetamine may increase the hypotensive activities of Guanadrel.Approved, Illicit, Investigational
AtenololGuanadrel may increase the hypotensive activities of Atenolol.Approved
AvanafilAvanafil may increase the antihypertensive activities of Guanadrel.Approved
BarnidipineGuanadrel may increase the antihypertensive activities of Barnidipine.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, Investigational
BethanidineBethanidine may increase the hypotensive activities of Guanadrel.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Guanadrel.Experimental
BimatoprostGuanadrel may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololGuanadrel may increase the hypotensive activities of Bisoprolol.Approved
BosentanBosentan may increase the hypotensive activities of Guanadrel.Approved, Investigational
BQ-123Guanadrel may increase the hypotensive activities of BQ-123.Investigational
BretyliumGuanadrel may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Guanadrel.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Guanadrel.Experimental
BupranololGuanadrel may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Guanadrel.Experimental
CafedrineGuanadrel may increase the hypotensive activities of Cafedrine.Investigational
CandesartanGuanadrel may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilGuanadrel may increase the hypotensive activities of Candesartan cilexetil.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
CicletanineGuanadrel may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilGuanadrel may increase the hypotensive activities of Cilazapril.Approved
ClonidineClonidine may increase the hypotensive activities of Guanadrel.Approved
CloranololGuanadrel may increase the hypotensive activities of Cloranolol.Experimental
CryptenamineGuanadrel may increase the hypotensive activities of Cryptenamine.Approved
CyclopenthiazideGuanadrel may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideGuanadrel may increase the hypotensive activities of Cyclothiazide.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Guanadrel.Approved, Investigational
DelaprilGuanadrel may increase the hypotensive activities of Delapril.Investigational
DeserpidineGuanadrel may increase the hypotensive activities of Deserpidine.Approved
DexniguldipineGuanadrel may increase the hypotensive activities of Dexniguldipine.Experimental
DiazoxideDiazoxide may increase the hypotensive activities of Guanadrel.Approved
DiclofenacThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DiethylnorspermineGuanadrel may increase the hypotensive activities of Diethylnorspermine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Guanadrel.Approved, Investigational
DiltiazemGuanadrel may increase the hypotensive activities of Diltiazem.Approved, Investigational
DipyridamoleDipyridamole may increase the antihypertensive activities of Guanadrel.Approved
DorzolamideGuanadrel may increase the hypotensive activities of Dorzolamide.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Guanadrel.Approved
EfonidipineGuanadrel may increase the hypotensive activities of Efonidipine.Approved, Investigational
EnalaprilGuanadrel may increase the hypotensive activities of Enalapril.Approved, Vet Approved
EnalaprilatGuanadrel may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Guanadrel.Experimental
EpanololGuanadrel may increase the hypotensive activities of Epanolol.Experimental
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
Ferulic acidGuanadrel may increase the hypotensive activities of Ferulic acid.Experimental
FosinoprilGuanadrel may increase the hypotensive activities of Fosinopril.Approved
FostamatinibFostamatinib may increase the antihypertensive activities of Guanadrel.Approved, Investigational
FurazolidoneFurazolidone may increase the hypotensive activities of Guanadrel.Approved, Investigational, Vet Approved
GuanabenzGuanadrel may increase the hypotensive activities of Guanabenz.Approved, Investigational
GuanazodineGuanadrel may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanadrel may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Guanadrel.Approved, Investigational
GuanoclorGuanadrel may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzGuanadrel may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanGuanadrel may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Guanadrel.Experimental
HexamethoniumGuanadrel may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Guanadrel.Experimental
HydralazineHydralazine may increase the hypotensive activities of Guanadrel.Approved
HydrochlorothiazideGuanadrel may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideGuanadrel may increase the hypotensive activities of Hydroflumethiazide.Approved, Investigational
IbuprofenThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Ibuprofen.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
IndoraminIndoramin may increase the hypotensive activities of Guanadrel.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, Investigational
KetanserinKetanserin may increase the hypotensive activities of Guanadrel.Investigational
KetorolacThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Ketorolac.Approved
LabetalolGuanadrel may increase the hypotensive activities of Labetalol.Approved
LacidipineGuanadrel may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostGuanadrel may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineGuanadrel may increase the hypotensive activities of Lercanidipine.Approved, Investigational
LinsidomineGuanadrel may increase the hypotensive activities of Linsidomine.Experimental
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, Investigational
MebanazineMebanazine may increase the hypotensive activities of Guanadrel.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Guanadrel.Approved, Investigational
MethoserpidineGuanadrel may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaGuanadrel may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Guanadrel.Approved, 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.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Guanadrel.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Guanadrel.Approved, Investigational
MirodenafilMirodenafil may increase the antihypertensive activities of Guanadrel.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Guanadrel.Approved, Investigational
MoexiprilGuanadrel may increase the hypotensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Guanadrel.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Guanadrel.Approved, Investigational
MuzolimineGuanadrel may increase the hypotensive activities of Muzolimine.Experimental
NadololGuanadrel may increase the hypotensive activities of Nadolol.Approved
NaftopidilGuanadrel may increase the hypotensive activities of Naftopidil.Investigational
NaproxenThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Naproxen.Approved, Vet Approved
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, Investigational
NicorandilGuanadrel may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineGuanadrel may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineGuanadrel may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineGuanadrel may increase the hypotensive activities of Nimodipine.Approved, Investigational
NisoldipineGuanadrel may increase the hypotensive activities of Nisoldipine.Approved
NitrendipineGuanadrel may increase the hypotensive activities of Nitrendipine.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Guanadrel.Approved, Investigational
ObinutuzumabGuanadrel may increase the hypotensive activities of Obinutuzumab.Approved, Investigational
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
PinacidilPinacidil may increase the hypotensive activities of Guanadrel.Approved
PindololGuanadrel may increase the hypotensive activities of Pindolol.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Guanadrel.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Guanadrel.Withdrawn
Platelet Activating FactorGuanadrel may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazideGuanadrel may increase the hypotensive activities of Polythiazide.Approved
PrazosinPrazosin may increase the hypotensive activities of Guanadrel.Approved
ProcaineProcaine may increase the hypotensive activities of Guanadrel.Approved, Investigational, Vet Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Guanadrel.Approved, Investigational
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, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Guanadrel.Approved, 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
Salicylic acidThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Salicylic acid.Approved, Investigational, Vet Approved
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
SulfasalazineThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Sulindac.Approved, Investigational
TadalafilTadalafil may increase the antihypertensive activities of Guanadrel.Approved, Investigational
TalinololGuanadrel may increase the hypotensive activities of Talinolol.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
TetrahydropalmatineGuanadrel may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineGuanadrel may increase the hypotensive activities of Theodrenaline.Investigational
TheophyllineTheophylline may increase the antihypertensive activities of Guanadrel.Approved
TiboloneGuanadrel may increase the hypotensive activities of Tibolone.Approved, Investigational
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
Tolfenamic AcidThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Tolfenamic Acid.Approved, Investigational
TolonidineGuanadrel may increase the hypotensive activities of Tolonidine.Experimental
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
TranylcypromineTranylcypromine may increase the hypotensive activities of Guanadrel.Approved, Investigational
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
TrimazosinTrimazosin may increase the hypotensive activities of Guanadrel.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Guanadrel.Approved, Investigational
Trolamine salicylateThe therapeutic efficacy of Guanadrel can be decreased when used in combination with Trolamine salicylate.Approved
UdenafilUdenafil may increase the antihypertensive activities of Guanadrel.Approved, Investigational
UnoprostoneGuanadrel may increase the hypotensive activities of Unoprostone.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Guanadrel.Investigational
ValsartanValsartan may increase the hypotensive activities of Guanadrel.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Guanadrel.Approved
VincamineGuanadrel may increase the hypotensive activities of Vincamine.Experimental
XipamideGuanadrel may increase the hypotensive activities of Xipamide.Experimental
XylometazolineGuanadrel may increase the hypotensive activities of Xylometazoline.Approved, Investigational
YohimbineYohimbine may decrease the antihypertensive activities of Guanadrel.Approved, Investigational, Vet Approved
ZofenoprilGuanadrel may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,547,951.

General References
Not Available
External Links
Human Metabolome Database
HMDB0014371
KEGG Drug
D00607
KEGG Compound
C07035
PubChem Compound
38521
PubChem Substance
46506457
ChemSpider
35305
ChEBI
5555
ChEMBL
CHEMBL1037
Therapeutic Targets Database
DAP000059
PharmGKB
PA164745308
Drugs.com
Drugs.com Drug Page
Wikipedia
Guanadrel

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Pharmaceutical Utilization Management Program VA Inc.
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)213.5-215U.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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Ketals
Alternative Parents
1,3-dioxolanes / Guanidines / Oxacyclic compounds / Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Ketal / Meta-dioxolane / Guanidine / Oxacycle / Organoheterocyclic compound / Carboximidamide / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
guanidines, spiroketal (CHEBI:5555)

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
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
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  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]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 07:45