Identification

Name
Bethanidine
Accession Number
DB00217  (APRD00825)
Type
Small Molecule
Groups
Approved
Description

A guanidinium antihypertensive agent that acts by blocking adrenergic transmission.

Structure
Thumb
Synonyms
  • Betanidina
  • Betanidine
  • Betanidinum
  • N,N'-dimethyl-N''-(phenylmethyl)-guanidine
Product Ingredients
IngredientUNIICASInChI Key
Bethanidine sulfateJ4THI5N7O2114-85-2YTIJUXVIZLYQTB-UHFFFAOYSA-N
International/Other Brands
Esbatal
Categories
UNII
W8S3YM7AUU
CAS number
55-73-2
Weight
Average: 177.2462
Monoisotopic: 177.126597495
Chemical Formula
C10H15N3
InChI Key
NIVZHWNOUVJHKV-UHFFFAOYSA-N
InChI
InChI=1S/C10H15N3/c1-11-10(12-2)13-8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H2,11,12,13)
IUPAC Name
(E)-3-benzyl-1,2-dimethylguanidine
SMILES
CN\C(NCC1=CC=CC=C1)=N/C

Pharmacology

Indication

For the treatment of hypertension.

Structured Indications
Not Available
Pharmacodynamics

Bethanidine is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission. The precise mode of action is not clear. Although bethanidine may produce adverse effects, they are beneficial in severe hypertension and produce fewer side effects than guanethidine.

Mechanism of action

Bethanidine, a guanidine derivative, is a peripherally acting antiadrenergic agent which primarily acts as an alpha2a adrenergic agonist. Bethanidine effectively decreases blood pressure by suppressing renin secretion or interfering with function of the sympathetic nervous system.

TargetActionsOrganism
AAlpha-2 adrenergic receptors
agonist
Human
AATP-sensitive inward rectifier potassium channel 1
inhibitor
Human
UBeta adrenergic receptor
antagonist
Human
Absorption

Absorbed rapidly in the gastrointestinal tract following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

9 hours (range 7 to 11 hours)

Clearance
Not Available
Toxicity
Not Available
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 Bethanidine.Experimental
AcebutololBethanidine may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Bethanidine.Approved, Investigational
AliskirenBethanidine may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololBethanidine may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmbrisentanBethanidine may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineBethanidine may increase the hypotensive activities of Amifostine.Approved, Investigational
AmineptineAmineptine may decrease the antihypertensive activities of Bethanidine.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Bethanidine.Approved
AmlodipineBethanidine may increase the hypotensive activities of Amlodipine.Approved
ArotinololBethanidine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololBethanidine may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
BefunololBethanidine may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
BenazeprilBethanidine may increase the hypotensive activities of Benazepril.Approved, Investigational
BendroflumethiazideBethanidine may increase the hypotensive activities of Bendroflumethiazide.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Bethanidine.Withdrawn
BepridilBethanidine may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBethanidine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololBethanidine may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BietaserpineBethanidine may increase the hypotensive activities of Bietaserpine.Experimental
BimatoprostBethanidine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololBethanidine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololBethanidine may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BosentanBethanidine may increase the hypotensive activities of Bosentan.Approved, Investigational
BQ-123Bethanidine may increase the hypotensive activities of BQ-123.Investigational
BretyliumBethanidine may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Bethanidine.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Bethanidine.Experimental
BucindololBethanidine may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BufuralolBethanidine may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BupranololBethanidine may increase the atrioventricular blocking (AV block) activities of Bupranolol.Approved
CadralazineBethanidine may increase the hypotensive activities of Cadralazine.Experimental
CafedrineBethanidine may increase the hypotensive activities of Cafedrine.Investigational
CandesartanBethanidine may increase the hypotensive activities of Candesartan.Approved
CandoxatrilBethanidine may increase the hypotensive activities of Candoxatril.Experimental
CaptoprilBethanidine may increase the hypotensive activities of Captopril.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Bethanidine.Withdrawn
CarteololBethanidine may increase the atrioventricular blocking (AV block) activities of Carteolol.Approved
CarvedilolBethanidine may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CeliprololBethanidine may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ChlorothiazideBethanidine may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneBethanidine may increase the hypotensive activities of Chlorthalidone.Approved
CicletanineBethanidine may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilBethanidine may increase the hypotensive activities of Cilazapril.Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Bethanidine.Approved, Vet Approved
ClonidineBethanidine may increase the hypotensive activities of Clonidine.Approved
CloranololBethanidine may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
CryptenamineBethanidine may increase the hypotensive activities of Cryptenamine.Approved
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Bethanidine.Approved
CyclopenthiazideBethanidine may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideBethanidine may increase the hypotensive activities of Cyclothiazide.Approved
DebrisoquinBethanidine may increase the hypotensive activities of Debrisoquin.Approved
DelaprilBethanidine may increase the hypotensive activities of Delapril.Experimental
DeserpidineBethanidine may increase the hypotensive activities of Deserpidine.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Bethanidine.Approved
DesvenlafaxineDesvenlafaxine may decrease the antihypertensive activities of Bethanidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Bethanidine.Approved
DibenzepinDibenzepin may decrease the antihypertensive activities of Bethanidine.Experimental
diethylnorspermineBethanidine may increase the hypotensive activities of diethylnorspermine.Investigational
DihydralazineBethanidine may increase the hypotensive activities of Dihydralazine.Investigational
DiltiazemBethanidine may increase the hypotensive activities of Diltiazem.Approved
DorzolamideBethanidine may increase the hypotensive activities of Dorzolamide.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Bethanidine.Approved
DoxazosinBethanidine may increase the hypotensive activities of Doxazosin.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Bethanidine.Approved
DuloxetineDuloxetine may decrease the antihypertensive activities of Bethanidine.Approved
EfonidipineBethanidine may increase the hypotensive activities of Efonidipine.Approved
EnalaprilBethanidine may increase the hypotensive activities of Enalapril.Approved, Vet Approved
EnalaprilatBethanidine may increase the hypotensive activities of Enalaprilat.Approved
EndralazineBethanidine may increase the hypotensive activities of Endralazine.Experimental
EpanololBethanidine may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
EpoprostenolBethanidine may increase the hypotensive activities of Epoprostenol.Approved
EprosartanBethanidine may increase the hypotensive activities of Eprosartan.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Bethanidine.Investigational
EsmololBethanidine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
FelodipineBethanidine may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamBethanidine may increase the hypotensive activities of Fenoldopam.Approved
Ferulic acidBethanidine may increase the hypotensive activities of Ferulic acid.Experimental
FosinoprilBethanidine may increase the hypotensive activities of Fosinopril.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Bethanidine.Approved, Vet Approved
GuanabenzBethanidine may increase the hypotensive activities of Guanabenz.Approved
GuanadrelBethanidine may increase the hypotensive activities of Guanadrel.Approved
GuanazodineBethanidine may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineBethanidine may increase the hypotensive activities of Guanethidine.Approved
GuanfacineBethanidine may increase the hypotensive activities of Guanfacine.Approved, Investigational
GuanoclorBethanidine may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzBethanidine may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanBethanidine may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Bethanidine.Experimental
HexamethoniumBethanidine may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Bethanidine.Experimental
HydralazineBethanidine may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideBethanidine may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideBethanidine may increase the hypotensive activities of Hydroflumethiazide.Approved
IloprostIloprost may increase the hypotensive activities of Bethanidine.Approved, Investigational
ImidaprilBethanidine may increase the hypotensive activities of Imidapril.Investigational
ImipramineImipramine may decrease the antihypertensive activities of Bethanidine.Approved
IndapamideBethanidine may increase the hypotensive activities of Indapamide.Approved
IndenololBethanidine may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminBethanidine may increase the hypotensive activities of Indoramin.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Bethanidine.Approved
IprindoleIprindole may decrease the antihypertensive activities of Bethanidine.Experimental
IproclozideIproclozide may increase the hypotensive activities of Bethanidine.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Bethanidine.Withdrawn
IrbesartanBethanidine may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Bethanidine.Approved
IsradipineBethanidine may increase the hypotensive activities of Isradipine.Approved
KetanserinBethanidine may increase the hypotensive activities of Ketanserin.Investigational
LabetalolBethanidine may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LacidipineBethanidine may increase the hypotensive activities of Lacidipine.Approved
LandiololBethanidine may increase the atrioventricular blocking (AV block) activities of Landiolol.Investigational
LatanoprostBethanidine may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineBethanidine may increase the hypotensive activities of Lercanidipine.Approved, Investigational
LevomilnacipranLevomilnacipran may decrease the antihypertensive activities of Bethanidine.Approved
LinsidomineBethanidine may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilBethanidine may increase the hypotensive activities of Lisinopril.Approved, Investigational
LofepramineLofepramine may decrease the antihypertensive activities of Bethanidine.Experimental
LofexidineBethanidine may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanBethanidine may increase the hypotensive activities of Losartan.Approved
MacitentanBethanidine may increase the hypotensive activities of Macitentan.Approved
ManidipineBethanidine may increase the hypotensive activities of Manidipine.Approved
MebanazineMebanazine may increase the hypotensive activities of Bethanidine.Withdrawn
MecamylamineBethanidine may increase the hypotensive activities of Mecamylamine.Approved
MepindololBethanidine may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
MethoserpidineBethanidine may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaBethanidine may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Bethanidine.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Bethanidine.Approved, Investigational
MetipranololBethanidine may increase the hypotensive activities of Metipranolol.Approved
MetolazoneBethanidine may increase the hypotensive activities of Metolazone.Approved
MetoprololBethanidine may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MetyrosineBethanidine may increase the hypotensive activities of Metyrosine.Approved
MianserinThe therapeutic efficacy of Bethanidine can be decreased when used in combination with Mianserin.Approved
MibefradilBethanidine may increase the hypotensive activities of Mibefradil.Withdrawn
MilnacipranMilnacipran may decrease the antihypertensive activities of Bethanidine.Approved
MinaprineMinaprine may increase the hypotensive activities of Bethanidine.Approved
MinoxidilBethanidine may increase the hypotensive activities of Minoxidil.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Bethanidine.Investigational
MirtazapineMirtazapine may decrease the antihypertensive activities of Bethanidine.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Bethanidine.Approved
MoexiprilBethanidine may increase the hypotensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Bethanidine.Approved
MoxonidineBethanidine may increase the hypotensive activities of Moxonidine.Approved
MuzolimineBethanidine may increase the hypotensive activities of Muzolimine.Experimental
NadololBethanidine may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NaftopidilBethanidine may increase the hypotensive activities of Naftopidil.Investigational
NebivololBethanidine may increase the hypotensive activities of Nebivolol.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Bethanidine.Withdrawn
NicardipineBethanidine may increase the hypotensive activities of Nicardipine.Approved
NicorandilBethanidine may increase the hypotensive activities of Nicorandil.Approved
NiguldipineBethanidine may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineBethanidine may increase the hypotensive activities of Nilvadipine.Approved
NimodipineBethanidine may increase the hypotensive activities of Nimodipine.Approved
NisoldipineBethanidine may increase the hypotensive activities of Nisoldipine.Approved
NitrendipineBethanidine may increase the hypotensive activities of Nitrendipine.Approved
NitroprussideBethanidine may increase the hypotensive activities of Nitroprusside.Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Bethanidine.Approved
ObinutuzumabBethanidine may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Bethanidine.Withdrawn
OlmesartanBethanidine may increase the hypotensive activities of Olmesartan.Approved, Investigational
OmapatrilatBethanidine may increase the hypotensive activities of Omapatrilat.Investigational
OpipramolOpipramol may decrease the antihypertensive activities of Bethanidine.Investigational
OxprenololBethanidine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
PargylinePargyline may increase the hypotensive activities of Bethanidine.Approved
PenbutololBethanidine may increase the atrioventricular blocking (AV block) activities of Penbutolol.Approved, Investigational
PentoliniumBethanidine may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Bethanidine.Approved, Investigational
PerindoprilBethanidine may increase the hypotensive activities of Perindopril.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Bethanidine.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Bethanidine.Withdrawn
PhenoxybenzamineBethanidine may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Bethanidine.Withdrawn
PhentolamineBethanidine may increase the hypotensive activities of Phentolamine.Approved
PinacidilBethanidine may increase the hypotensive activities of Pinacidil.Withdrawn
PindololBethanidine may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved
PirlindolePirlindole may increase the hypotensive activities of Bethanidine.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Bethanidine.Withdrawn
PolythiazideBethanidine may increase the hypotensive activities of Polythiazide.Approved
PractololBethanidine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinBethanidine may increase the hypotensive activities of Prazosin.Approved
PropranololBethanidine may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Bethanidine.Approved
QuinaprilBethanidine may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Bethanidine.Approved
RamiprilBethanidine may increase the hypotensive activities of Ramipril.Approved
RasagilineRasagiline may increase the hypotensive activities of Bethanidine.Approved
RemikirenBethanidine may increase the hypotensive activities of Remikiren.Approved
RescinnamineBethanidine may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Bethanidine.Approved
RilmenidineBethanidine may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatBethanidine may increase the hypotensive activities of Riociguat.Approved
RituximabBethanidine may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Bethanidine.Withdrawn
SaprisartanBethanidine may increase the hypotensive activities of Saprisartan.Experimental
SelegilineSelegiline may increase the hypotensive activities of Bethanidine.Approved, Investigational, Vet Approved
SelexipagBethanidine may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Bethanidine.Approved, Investigational
SitaxentanBethanidine may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SotalolBethanidine may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
SpiraprilBethanidine may increase the hypotensive activities of Spirapril.Approved
TadalafilTadalafil may increase the antihypertensive activities of Bethanidine.Approved, Investigational
TalinololBethanidine may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
TelmisartanBethanidine may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilBethanidine may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinBethanidine may increase the hypotensive activities of Terlipressin.Approved, Investigational
TertatololBethanidine may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
TetrahydropalmatineBethanidine may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineBethanidine may increase the hypotensive activities of Theodrenaline.Investigational
TianeptineTianeptine may decrease the antihypertensive activities of Bethanidine.Approved
TiboloneBethanidine may increase the hypotensive activities of Tibolone.Approved
TicrynafenBethanidine may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololBethanidine may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
TolazolineBethanidine may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
TolonidineBethanidine may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Bethanidine.Approved
TorasemideBethanidine may increase the hypotensive activities of Torasemide.Approved
TrandolaprilBethanidine may increase the hypotensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Bethanidine.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Bethanidine.Approved
TravoprostBethanidine may increase the hypotensive activities of Travoprost.Approved
TreprostinilBethanidine may increase the hypotensive activities of Treprostinil.Approved, Investigational
TrichlormethiazideBethanidine may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinBethanidine may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanBethanidine may increase the hypotensive activities of Trimethaphan.Approved
TrimipramineTrimipramine may decrease the antihypertensive activities of Bethanidine.Approved
UdenafilUdenafil may increase the antihypertensive activities of Bethanidine.Approved, Investigational
UnoprostoneBethanidine may increase the hypotensive activities of Unoprostone.Approved
UrapidilBethanidine may increase the hypotensive activities of Urapidil.Investigational
ValsartanBethanidine may increase the hypotensive activities of Valsartan.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Bethanidine.Approved
VenlafaxineVenlafaxine may decrease the antihypertensive activities of Bethanidine.Approved
VincamineBethanidine may increase the hypotensive activities of Vincamine.Experimental
VinpocetineBethanidine may increase the hypotensive activities of Vinpocetine.Investigational
XipamideBethanidine may increase the hypotensive activities of Xipamide.Experimental
XylometazolineBethanidine may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Bethanidine.Approved, Vet Approved
ZofenoprilBethanidine may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Khashayar Karimian, Keshava Murthy, Darren Hall, "Methods of making ureas and guanidines, including terazosin, prazosin, doxazosin, tiodazosin, trimazosin, quinazosin, and bunazosin (exemplary of 2-substituted quinazoline compounds), and meobentine, and bethanidine and intermediates thereof." U.S. Patent US5686612, issued November, 1990.

US5686612
General References
Not Available
External Links
Human Metabolome Database
HMDB14362
KEGG Drug
D01603
PubChem Compound
2368
PubChem Substance
46507605
ChemSpider
2278
ChEBI
37937
ChEMBL
CHEMBL1201260
Therapeutic Targets Database
DAP000047
PharmGKB
PA164743235
ATC Codes
C02CC01 — Betanidine
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Ah robins co
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196 °CPhysProp
logP0.49Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 mg/mLALOGPS
logP1.41ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.42 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.5 m3·mol-1ChemAxon
Polarizability20.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9713
Blood Brain Barrier+0.85
Caco-2 permeable+0.5072
P-glycoprotein substrateNon-substrate0.5681
P-glycoprotein inhibitor INon-inhibitor0.9217
P-glycoprotein inhibitor IINon-inhibitor0.6727
Renal organic cation transporterInhibitor0.5516
CYP450 2C9 substrateNon-substrate0.7952
CYP450 2D6 substrateNon-substrate0.5
CYP450 3A4 substrateNon-substrate0.7359
CYP450 1A2 substrateNon-inhibitor0.7802
CYP450 2C9 inhibitorNon-inhibitor0.9218
CYP450 2D6 inhibitorInhibitor0.5754
CYP450 2C19 inhibitorNon-inhibitor0.8195
CYP450 3A4 inhibitorNon-inhibitor0.8329
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9069
Ames testNon AMES toxic0.7985
CarcinogenicityNon-carcinogens0.886
BiodegradationNot ready biodegradable0.9161
Rat acute toxicity2.5507 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9126
hERG inhibition (predictor II)Non-inhibitor0.9191
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 benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Monocyclic benzene moiety / Guanidine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Imine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
guanidines (CHEBI:37937)

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Components:
References
  1. Noshiro T, Miura Y, Kimura S, Meguro Y, Sugawara T, Ohashi H, Takahashi M, Sano N, Watanabe H, Ohzeki T, et al.: Functional relationships between platelet alpha 2-adrenoceptors and sympathetic nerve activity in clinical hypertensive states. J Hypertens. 1990 Dec;8(12):1097-104. [PubMed:1962798]
  2. Noshiro T, Miura Y, Kimura S, Meguro Y, Sugawara T, Ohashi H, Takahashi M, Sano N, Watanabe H, Ohzeki T, et al.: Functional relationship between platelet alpha 2-adrenoceptors and sympathetic nerve activity in man. Clin Exp Hypertens A. 1989;11 Suppl 1:287-94. [PubMed:2545383]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Phosphatidylinositol-4,5-bisphosphate binding
Specific Function
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than...
Gene Name
KCNJ1
Uniprot ID
P48048
Uniprot Name
ATP-sensitive inward rectifier potassium channel 1
Molecular Weight
44794.6 Da
References
  1. Bkaily G, Caille JP, Payet MD, Peyrow M, Sauve R, Renaud JF, Sperelakis N: Bethanidine increases one type of potassium current and relaxes aortic muscle. Can J Physiol Pharmacol. 1988 Jun;66(6):731-6. [PubMed:3167688]
  2. Bkaily G: Bethanidine, nitroprusside and atrial natriuretic factor open a cGMP-sensitive K+ channel in aortic muscle. Prog Clin Biol Res. 1990;327:507-15. [PubMed:2157221]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...

Components:
References
  1. Hart GR, Anderson RJ: Withdrawal syndromes and the cessation of antihypertensive therapy. Arch Intern Med. 1981 Aug;141(9):1125-7. [PubMed:6114720]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Bacaner MB, Benditt DG: Antiarrhythmic, antifibrillatory, and hemodynamic actions of bethanidine sulfate: an orally effective analog of bretylium for suppression of ventricular tachyarrhythmias. Am J Cardiol. 1982 Oct;50(4):728-34. [PubMed:6812406]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:33