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targets (4)
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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Betanidine
Bethanidine sulfate
Salts Not Available
Brand names
Name Company
Esbatal
Tenathan
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Adrenergic Agents
  • Sympatholytics
CAS number 55-73-2
Weight Average: 177.2462
Monoisotopic: 177.126597495
Chemical Formula C10H15N3
InChI Key InChIKey=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)
Plain Text
IUPAC Name
(E)-3-benzyl-1,2-dimethylguanidine
SMILES
CN\C(NCC1=CC=CC=C1)=N/C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of hypertension.
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.
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
Pharmacoeconomics
Manufacturers
  • Ah robins co
Packagers Not Available
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 196 °C PhysProp
logP 0.49 Not Available
Predicted Properties
Property Value Source
water solubility 1.58e+00 g/l ALOGPS
logP 1.41 ALOGPS
logP 1.27 ChemAxon
logS -2 ALOGPS
pKa (strongest basic) 12.41 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 36.42 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 54.5 ChemAxon
polarizability 20.43 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01603 Link_out
ChEBI 37937 Link_out
ChEMBL 37937 Link_out
Therapeutic Targets Database DAP000047 Link_out
PharmGKB PA164743235 Link_out
ATC Codes
  • C02CC01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Alpha-2C adrenergic receptor

Pharmacological action: yes
Actions: agonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins

Organism class: human
UniProt ID: P18825 Link_out
Gene: ADRA2C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  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
  3. 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
  4. 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. Alpha-2A adrenergic receptor

Pharmacological action: unknown
Actions: agonist

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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  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

3. Alpha-2B adrenergic receptor

Pharmacological action: unknown
Actions: agonist

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 clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol

Organism class: human
UniProt ID: P18089 Link_out
Gene: ADRA2B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  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

4. ATP-sensitive inward rectifier potassium channel 1

Pharmacological action: yes
Actions: inhibitor

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 out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium

Organism class: human
UniProt ID: P48048 Link_out
Gene: KCNJ1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19