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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
Salts
Name/CAS Structure Properties
Bethanidine sulfate
114-85-2
Thumb
  • InChI Key: YTIJUXVIZLYQTB-UHFFFAOYSA-N
  • Monoisotopic Mass: 452.220574232
  • Average Mass: 452.571
DBSALT000194
Brand names
NameCompany
EsbatalNot Available
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsGuanidines; Polyamines; Amidines
Substituentsguanidine; amidine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9713
Blood Brain Barrier + 0.85
Caco-2 permeable + 0.5072
P-glycoprotein substrate Non-substrate 0.5681
P-glycoprotein inhibitor I Non-inhibitor 0.9217
P-glycoprotein inhibitor II Non-inhibitor 0.6727
Renal organic cation transporter Inhibitor 0.5516
CYP450 2C9 substrate Non-substrate 0.7952
CYP450 2D6 substrate Non-substrate 0.5
CYP450 3A4 substrate Non-substrate 0.7359
CYP450 1A2 substrate Non-inhibitor 0.7802
CYP450 2C9 substrate Non-inhibitor 0.9218
CYP450 2D6 substrate Inhibitor 0.5754
CYP450 2C19 substrate Non-inhibitor 0.8195
CYP450 3A4 substrate Non-inhibitor 0.8329
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9069
Ames test Non AMES toxic 0.7985
Carcinogenicity Non-carcinogens 0.886
Biodegradation Not ready biodegradable 0.9161
Rat acute toxicity 2.5507 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9126
hERG inhibition (predictor II) Non-inhibitor 0.9191
Pharmacoeconomics
Manufacturers
  • Ah robins co
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point196 °CPhysProp
logP0.49Not Available
Predicted Properties
PropertyValueSource
water solubility1.58e+00 g/lALOGPS
logP1.41ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (strongest basic)12.41ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area36.42ChemAxon
rotatable bond count2ChemAxon
refractivity54.5ChemAxon
polarizability20.43ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD01603
ChEBI37937
ChEMBLCHEMBL1201260
Therapeutic Targets DatabaseDAP000047
PharmGKBPA164743235
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