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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15N3
Molecular Weight 177.2462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETHANIDINE

SMILES

CNC(NC)=NCC1=CC=CC=C1

InChI

InChIKey=NIVZHWNOUVJHKV-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C10H15N3
Molecular Weight 177.2462
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Bethanidine is a post-ganglionic adrenergic neurone-blocking agent which exerts a marked postural hypotensive effect. The precise mechanism whereby bethanidine causes blockade of adrenergic neurones is unknown. An initial sympathomimetic effect has been demonstrated in man and animals, possibly due to release of catecholamines.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TENATHAN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.4 μg/mL
25 mg single, intravenous
BETHANIDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.5 μg × h/mL
25 mg single, intravenous
BETHANIDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
25 mg single, intravenous
BETHANIDINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
25 mg single, intravenous
BETHANIDINE plasma
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
Initial therapy 0.228 mg/kg 8 hourly Maintenance therapy 0.114 to 0.228 mg/kg 8 hourly
Route of Administration: Oral
In Vitro Use Guide
The effects of bethanidine sulphate, a pharmacological analog of the cardiac antibrillatory drug, bretylium tosylate, were studied on action potentials (APs) and K+, Na+, and Ca2+ currents of single cultured embryonic chick heart cells using the whole-cell current clamp and voltage clamp technique. Extracellular application of bethanidine (0.3 mM) increased the overshoot and the duration of the APs and greatly decreased the outward K+ current (IK) and potentiated the inward fast Na+ currents (INa) and the inward slow calcium current (ICa). However, intracellular introduction of bethanidine (0.1 mM) blocked INa.
Substance Class Chemical
Record UNII
W8S3YM7AUU
Record Status Validated (UNII)
Record Version