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Identification
NameGuanethidine
Accession NumberDB01170  (APRD01007)
TypeSmall Molecule
GroupsApproved
DescriptionAn 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
Thumb
Synonyms
(2-(hexahydro-1(2h)-azocinyl)ethyl)guanidine
(2-(Octahydro-1-azocinyl)ethyl)guanidine
2-(1-N,N-Heptamethyleneimino)ethylguanidine
2-(1'-Azacyclooctyl)ethylguanidine
Azocine, 1-(2-guanidinoethyl)octahydro-
guanéthidine
guanethidinum
guanetidina
Guanidine, (2-(hexahydro-1(2H)-azocinyl)ethyl)-
Heptamethylenimine, 1-(2-guanidinoethyl)-
N-(2-Perhydroazocin-1-ylethyl)guanidine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Guanethidine 10 Tab 10mgTablet10 mgOralPro Doc Limitee1984-12-311999-08-12Canada
Ismelin 25mgTablet25 mgOralCiba Pharmaceuticals, Ciba Geigy Canada Ltd.1960-12-311996-09-09Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Guanethidine Sulfate Tab 10mgTablet10 mgOralApotex Inc1977-12-312013-03-28Canada
Apo Guanethidine Sulfate Tab 25mgTablet25 mgOralApotex Inc1977-12-312013-03-28Canada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
IsmedineChen Ho
IsmelinAmdipharm
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Guanethidine monosulfate
645-43-2
Thumb
  • InChI Key: YUFWAVFNITUSHI-UHFFFAOYSA-N
  • Monoisotopic Mass: 296.151826443
  • Average Mass: 296.39
DBSALT001071
Guanethidine sulfate
60-02-6
Thumb
  • InChI Key: NBJGGHFXCGHTNJ-UHFFFAOYSA-N
  • Monoisotopic Mass: 494.336273167
  • Average Mass: 494.7
DBSALT001861
Categories
UNIIZTI6C33Q2Q
CAS number55-65-2
WeightAverage: 198.3085
Monoisotopic: 198.184446724
Chemical FormulaC10H22N4
InChI KeyACGDKVXYNVEAGU-UHFFFAOYSA-N
InChI
InChI=1S/C10H22N4/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14/h1-9H2,(H4,11,12,13)
IUPAC Name
2-[2-(azocan-1-yl)ethyl]guanidine
SMILES
NC(N)=NCCN1CCCCCCC1
Pharmacology
IndicationFor the treatment of moderate and severe hypertension, either alone or as an adjunct, and for the treatment of renal hypertension.
Structured Indications Not Available
PharmacodynamicsHigh blood pressure can cause the heart and arteries to 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. Guanethidine works by decreasing the heart rate and relaxing the blood vessels so that blood can flow more easily through the body, thereby reducing these risks. It is a postganglionic sympathetic nerve terminal blocker that prevents the release of norepinephrine from nerve terminals.
Mechanism of actionGuanethidine acts at the sympathetic neuroeffector junction by inhibiting or interfering with the release and/or distribution of norepinephrine, rather than acting at the effector cell by inhibiting the association of norepinephrine with its receptors. It is taken up by norepinephrine transporters. It becomes concentrated in NE transmitter vesicles, replacing NE in these vesicles. This leads to a gradual depletion of NE stores in the nerve endings. Once inside the terminal it blocks the release of noradrenaline in response to arrival of an action potential. In contrast to ganglionic blocking agents, Guanethidine suppresses equally the responses mediated by alpha-and beta-adrenergic receptors but does not produce parasympathetic blockade. Since sympathetic blockade results in modest decreases in peripheral resistance and cardiac output, Guanethidine lowers blood pressure in the supine position. It further reduces blood pressure by decreasing the degree of vasoconstriction that normally results from reflex sympathetic nervous activity upon assumption of the upright posture, thus reducing venous return and cardiac output more.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium-dependent noradrenaline transporterProteinyes
inducer
HumanP23975 details
Related Articles
Absorption3-30% of oral dose (poor and highly variable)
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Guanethidine is converted by the liver to three metabolites, which are excreted in the urine. The metabolites are pharmacologically less active than the parent compound.

Route of eliminationIsmelin is converted by the liver to three metabolites, which are excreted in the urine.
Half life1.5 days
Clearance
  • Renal cl=56 ml/min
ToxicitySide effects include drowsiness, dizziness, tiredness or confusion. LD50=1000 mg/kg (mouse, oral)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineThe serum concentration of 2,5-Dimethoxy-4-ethylamphetamine can be decreased when it is combined with Guanethidine.Experimental, Illicit
3,4-MethylenedioxyamphetamineThe serum concentration of 3,4-Methylenedioxyamphetamine can be decreased when it is combined with Guanethidine.Experimental, Illicit
3,4-MethylenedioxymethamphetamineThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Guanethidine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineThe serum concentration of 4-Bromo-2,5-dimethoxyamphetamine can be decreased when it is combined with Guanethidine.Experimental, Illicit
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Guanethidine.Experimental
AcebutololGuanethidine may increase the hypotensive activities of Acebutolol.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Guanethidine.Approved, Investigational
AliskirenGuanethidine may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Guanethidine.Approved, Withdrawn
AmbrisentanGuanethidine may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineGuanethidine may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Guanethidine.Approved
AmphetamineThe serum concentration of Amphetamine can be decreased when it is combined with Guanethidine.Approved, Illicit
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Guanethidine.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Guanethidine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Guanethidine.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Guanethidine.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Guanethidine.Withdrawn
BenzphetamineThe serum concentration of Benzphetamine can be decreased when it is combined with Guanethidine.Approved, Illicit
BepridilGuanethidine may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Guanethidine.Approved
BethanidineBethanidine may increase the hypotensive activities of Guanethidine.Approved
BimatoprostBimatoprost may increase the hypotensive activities of Guanethidine.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Guanethidine.Approved
BosentanBosentan may increase the hypotensive activities of Guanethidine.Approved, Investigational
BretyliumBretylium may increase the hypotensive activities of Guanethidine.Approved
BrimonidineBrimonidine may increase the hypotensive activities of Guanethidine.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Guanethidine.Approved
BupranololGuanethidine may increase the hypotensive activities of Bupranolol.Approved
CandesartanCandesartan may increase the hypotensive activities of Guanethidine.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Guanethidine.Experimental
CaptoprilGuanethidine may increase the hypotensive activities of Captopril.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Guanethidine.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Guanethidine.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Guanethidine.Approved, Investigational
CeliprololGuanethidine may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideChlorothiazide may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
ChlorphentermineThe serum concentration of Chlorphentermine can be decreased when it is combined with Guanethidine.Illicit, Withdrawn
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Guanethidine.Approved
CilazaprilGuanethidine may increase the hypotensive activities of Cilazapril.Approved
ClonidineClonidine may increase the hypotensive activities of Guanethidine.Approved
CryptenamineCryptenamine may increase the hypotensive activities of Guanethidine.Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Guanethidine.Approved
DebrisoquinGuanethidine may increase the hypotensive activities of Debrisoquin.Approved
DeserpidineGuanethidine may increase the hypotensive activities of Deserpidine.Approved
DextroamphetamineThe serum concentration of Dextroamphetamine can be decreased when it is combined with Guanethidine.Approved, Illicit
DiazoxideDiazoxide may increase the hypotensive activities of Guanethidine.Approved
DiethylpropionThe serum concentration of Diethylpropion can be decreased when it is combined with Guanethidine.Approved, Illicit
DihydralazineGuanethidine may increase the hypotensive activities of Dihydralazine.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Guanethidine.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Guanethidine.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Guanethidine.Approved
EfonidipineGuanethidine may increase the hypotensive activities of Efonidipine.Approved
EnalaprilEnalapril may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
EnalaprilatGuanethidine may increase the hypotensive activities of Enalaprilat.Approved
EpoprostenolGuanethidine may increase the hypotensive activities of Epoprostenol.Approved
EprosartanEprosartan may increase the hypotensive activities of Guanethidine.Approved
FelodipineFelodipine may increase the hypotensive activities of Guanethidine.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Guanethidine.Approved
FosinoprilFosinopril may increase the hypotensive activities of Guanethidine.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Guanethidine.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Guanethidine.Approved, Investigational
HexamethoniumGuanethidine may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Guanethidine.Approved
HydralazineGuanethidine may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Guanethidine.Approved
Hydroxyamphetamine hydrobromideThe serum concentration of Hydroxyamphetamine hydrobromide can be decreased when it is combined with Guanethidine.Approved
IloprostIloprost may increase the hypotensive activities of Guanethidine.Approved, Investigational
ImidaprilGuanethidine may increase the hypotensive activities of Imidapril.Investigational
IndapamideIndapamide may increase the hypotensive activities of Guanethidine.Approved
IndenololGuanethidine may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminGuanethidine may increase the hypotensive activities of Indoramin.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Guanethidine.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Guanethidine.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Guanethidine.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Guanethidine.Approved
IsradipineIsradipine may increase the hypotensive activities of Guanethidine.Approved
KetanserinGuanethidine may increase the hypotensive activities of Ketanserin.Investigational
LabetalolLabetalol may increase the hypotensive activities of Guanethidine.Approved
LacidipineGuanethidine may increase the hypotensive activities of Lacidipine.Approved
LatanoprostLatanoprost may increase the hypotensive activities of Guanethidine.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Guanethidine.Approved, Investigational
LisdexamfetamineThe serum concentration of Lisdexamfetamine can be decreased when it is combined with Guanethidine.Approved, Investigational
LisinoprilLisinopril may increase the hypotensive activities of Guanethidine.Approved, Investigational
LofexidineGuanethidine may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Guanethidine.Approved
MacitentanGuanethidine may increase the hypotensive activities of Macitentan.Approved
ManidipineGuanethidine may increase the hypotensive activities of Manidipine.Approved
MebanazineMebanazine may increase the hypotensive activities of Guanethidine.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Guanethidine.Approved
MephedroneThe serum concentration of Mephedrone can be decreased when it is combined with Guanethidine.Investigational
MephentermineThe serum concentration of Mephentermine can be decreased when it is combined with Guanethidine.Approved
MethamphetamineThe serum concentration of Methamphetamine can be decreased when it is combined with Guanethidine.Approved, Illicit
MethyldopaMethyldopa may increase the hypotensive activities of Guanethidine.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Guanethidine.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Guanethidine.Approved, Investigational
MetipranololGuanethidine may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Guanethidine.Approved
MetoprololMetoprolol may increase the hypotensive activities of Guanethidine.Approved, Investigational
MetyrosineGuanethidine may increase the hypotensive activities of Metyrosine.Approved
MibefradilGuanethidine may increase the hypotensive activities of Mibefradil.Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Guanethidine.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Guanethidine.Approved
MMDAThe serum concentration of MMDA can be decreased when it is combined with Guanethidine.Experimental, Illicit
MoclobemideMoclobemide may increase the hypotensive activities of Guanethidine.Approved
MoexiprilMoexipril may increase the hypotensive activities of Guanethidine.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Guanethidine.Approved
MoxonidineGuanethidine may increase the hypotensive activities of Moxonidine.Approved
NadololGuanethidine may increase the hypotensive activities of Nadolol.Approved
NaftopidilGuanethidine may increase the hypotensive activities of Naftopidil.Investigational
NebivololGuanethidine may increase the hypotensive activities of Nebivolol.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Guanethidine.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Guanethidine.Approved
NicorandilGuanethidine may increase the hypotensive activities of Nicorandil.Approved
NiguldipineGuanethidine may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineGuanethidine may increase the hypotensive activities of Nilvadipine.Approved
NimodipineNimodipine may increase the hypotensive activities of Guanethidine.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Guanethidine.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Guanethidine.Approved
NitroprussideNitroprusside may increase the hypotensive activities of Guanethidine.Approved
ObinutuzumabGuanethidine may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Guanethidine.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Guanethidine.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Guanethidine.Investigational
OxprenololGuanethidine may increase the hypotensive activities of Oxprenolol.Approved
PargylinePargyline may increase the hypotensive activities of Guanethidine.Approved
PenbutololGuanethidine may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumPentolinium may increase the hypotensive activities of Guanethidine.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Guanethidine.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Guanethidine.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Guanethidine.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Guanethidine.Withdrawn
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Guanethidine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Guanethidine.Withdrawn
PhentermineThe serum concentration of Phentermine can be decreased when it is combined with Guanethidine.Approved, Illicit
PhentolaminePhentolamine may increase the hypotensive activities of Guanethidine.Approved
PinacidilGuanethidine may increase the hypotensive activities of Pinacidil.Withdrawn
PindololPindolol may increase the hypotensive activities of Guanethidine.Approved
PirlindolePirlindole may increase the hypotensive activities of Guanethidine.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Guanethidine.Withdrawn
PolythiazideGuanethidine may increase the hypotensive activities of Polythiazide.Approved
PrazosinPrazosin may increase the hypotensive activities of Guanethidine.Approved
PropranololPropranolol may increase the hypotensive activities of Guanethidine.Approved, Investigational
PseudoephedrineThe serum concentration of Pseudoephedrine can be decreased when it is combined with Guanethidine.Approved
QuinaprilQuinapril may increase the hypotensive activities of Guanethidine.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Guanethidine.Approved
RamiprilRamipril may increase the hypotensive activities of Guanethidine.Approved
RasagilineRasagiline may increase the hypotensive activities of Guanethidine.Approved
RemikirenRemikiren may increase the hypotensive activities of Guanethidine.Approved
RescinnamineGuanethidine may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Guanethidine.Approved
RilmenidineGuanethidine may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatGuanethidine may increase the hypotensive activities of Riociguat.Approved
RitobegronThe serum concentration of Ritobegron can be decreased when it is combined with Guanethidine.Investigational
RituximabGuanethidine may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Guanethidine.Withdrawn
SaprisartanGuanethidine may increase the hypotensive activities of Saprisartan.Experimental
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Guanethidine.Approved
SelegilineSelegiline may increase the hypotensive activities of Guanethidine.Approved, Investigational, Vet Approved
SelexipagGuanethidine may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Guanethidine.Approved, Investigational
SitaxentanGuanethidine may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilGuanethidine may increase the hypotensive activities of Spirapril.Approved
TadalafilTadalafil may increase the antihypertensive activities of Guanethidine.Approved, Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Guanethidine.Approved, Investigational
TemocaprilGuanethidine may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinGuanethidine may increase the hypotensive activities of Terlipressin.Approved, Investigational
TiboloneGuanethidine may increase the hypotensive activities of Tibolone.Approved
TicrynafenGuanethidine may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Guanethidine.Approved
TolazolineTolazoline may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
ToloxatoneToloxatone may increase the hypotensive activities of Guanethidine.Approved
TorasemideTorasemide may increase the hypotensive activities of Guanethidine.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Guanethidine.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Guanethidine.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Guanethidine.Approved
TravoprostTravoprost may increase the hypotensive activities of Guanethidine.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Guanethidine.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Guanethidine.Approved, Vet Approved
TrimazosinGuanethidine may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Guanethidine.Approved
UdenafilUdenafil may increase the antihypertensive activities of Guanethidine.Approved, Investigational
UnoprostoneGuanethidine may increase the hypotensive activities of Unoprostone.Approved
ValsartanValsartan may increase the hypotensive activities of Guanethidine.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Guanethidine.Approved
VinpocetineGuanethidine may increase the hypotensive activities of Vinpocetine.Investigational
XylometazolineGuanethidine may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Guanethidine.Approved, Vet Approved
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

U.S. Patent 2,928,829
U.S. Patent 3,006,913
U.S. Patent 3,055,882

General ReferencesNot Available
External Links
ATC CodesC02LF01C02CC02S01EX01
AHFS Codes
  • 24:08.32
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.5 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.945
Blood Brain Barrier+0.9015
Caco-2 permeable-0.5683
P-glycoprotein substrateSubstrate0.7743
P-glycoprotein inhibitor INon-inhibitor0.9342
P-glycoprotein inhibitor IIInhibitor0.5063
Renal organic cation transporterInhibitor0.7586
CYP450 2C9 substrateNon-substrate0.8981
CYP450 2D6 substrateSubstrate0.6426
CYP450 3A4 substrateNon-substrate0.7884
CYP450 1A2 substrateNon-inhibitor0.908
CYP450 2C9 inhibitorNon-inhibitor0.9363
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.939
CYP450 3A4 inhibitorNon-inhibitor0.9611
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9748
Ames testNon AMES toxic0.6626
CarcinogenicityNon-carcinogens0.9595
BiodegradationNot ready biodegradable0.9883
Rat acute toxicity2.4210 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6083
hERG inhibition (predictor II)Non-inhibitor0.8115
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral10 mg
TabletOral25 mg
Prices
Unit descriptionCostUnit
Guanethidine monosulf powder102.0USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point276-281U.S. Patent 2,928,829 U.S. Patent 3,006,913 U.S. Patent 3,055,882
water solubilityVery solubleNot Available
logP0.8Not Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassGuanidines
Sub ClassNot Available
Direct ParentGuanidines
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hydrocarbon derivative
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inducer
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. 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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23