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Identification
NameBethanidine
Accession NumberDB00217  (APRD00825)
TypeSmall Molecule
GroupsApproved
Description

A guanidinium antihypertensive agent that acts by blocking adrenergic transmission.

Structure
Thumb
Synonyms
SynonymLanguageCode
BetanidinaNot AvailableNot Available
BetanidineNot AvailableINN
BetanidinumNot AvailableNot Available
N,N'-dimethyl-N''-(phenylmethyl)-guanidineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
EsbatalNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Bethanidine sulfate
114-85-2
Thumb
  • InChI Key: YTIJUXVIZLYQTB-UHFFFAOYSA-N
  • Monoisotopic Mass: 452.220574232
  • Average Mass: 452.571
DBSALT000194
Categories
CAS number55-73-2
WeightAverage: 177.2462
Monoisotopic: 177.126597495
Chemical FormulaC10H15N3
InChI KeyNIVZHWNOUVJHKV-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Phenylmethylamine
  • Benzylamine
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of hypertension.
PharmacodynamicsBethanidine 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 actionBethanidine, 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.
AbsorptionAbsorbed rapidly in the gastrointestinal tract following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life9 hours (range 7 to 11 hours)
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9218
CYP450 2D6 substrateInhibitor0.5754
CYP450 2C19 substrateNon-inhibitor0.8195
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Ah robins co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point196 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesC02CC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Alpha-2 adrenergic receptor

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details
Alpha-2B adrenergic receptor P18089 Details
Alpha-2C adrenergic receptor P18825 Details

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
  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

2. ATP-sensitive inward rectifier potassium channel 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
ATP-sensitive inward rectifier potassium channel 1 P48048 Details

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
  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

3. Beta adrenergic receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details
Beta-2 adrenergic receptor P07550 Details
Beta-3 adrenergic receptor P13945 Details

References:

  1. Hart GR, Anderson RJ: Withdrawal syndromes and the cessation of antihypertensive therapy. Arch Intern Med. 1981 Aug;141(9):1125-7. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08