BETHANIDINE

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6065986

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 Target	Pharmacology	Condition	Potency
adrenergic receptor signaling pathway involved in heart process 2 Target ID: GO:0086023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7066153 \| https://www.ncbi.nlm.nih.gov/pubmed/6065986	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1749117/pdf/brmedj02317-0037.pdf http://www.sciencedirect.com/science/article/pii/S0140673664924754 https://www.ncbi.nlm.nih.gov/pubmed/641213	Primary		Approved 8583	TENATHAN Approved Use Bethanidine (Sulphate) is used in hypertension to reduce the blood pressure.

C_max

Value	Dose	Co-administered	Analyte	Population
0.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120401/	25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered:		BETHANIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120401/	25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered:		BETHANIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120401/	25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered:		BETHANIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1120401/	25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered:		BETHANIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
40 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 40 mg/kg, 1 times / day Route: oral Route: multiple Dose: 40 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3897340	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/3897340	Sources: https://pubmed.ncbi.nlm.nih.gov/3897340

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:37937	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:37937
ZINC	ZINC000002041046	http://zinc15.docking.org/substances/ZINC000002041046

PubMed

Title	Date	PubMed
Demosponge EST sequencing reveals a complex genetic toolkit of the simplest metazoans.	2010-12	20621960
Prediction of Daily Patient Numbers for a Regional Emergency Medical Center using Time Series Analysis.	2010-09	21818435
Treatment outcome in patients receiving assertive community treatment.	2010-08	19847646
Biological characterisation of Haliclona (?gellius) sp.: sponge and associated microorganisms.	2009-11	19471996
Sponge spicules as blueprints for the biofabrication of inorganic-organic composites and biomaterials.	2009-06	19430775
Ribotoxin genes in isolates of Aspergillus section Clavati.	2008-10	18600469
The "Health Benefit Basket" in Denmark: a description of entitlements, actors, and decision-making processes in the curative health sector.	2005-12	16270211
eCAM benefits from diversity that derives from CAM.	2005-09	16136204
The aggressive treatment of hypertension.	2003-05-03	12737860
Studies on bethanidine and meobentine: direct and indirect effects of antifibrillatory drugs.	1986-11-01	2434745
Bethanidine sulfate: efficacy in prevention of ventricular tachyarrhythmias during programmed stimulation. Report of a multicenter study of 56 patients.	1985-09	3897340
Acute electrophysiologic effects of bethanidine sulfate in patients with ventricular tachycardia or fibrillation.	1984-11	6496282
Antiarrhythmic action of bethanidine.	1984-08-01	6465015
Antiarrhythmic and electrophysiologic actions of bethanidine sulfate in primary ventricular fibrillation or life-threatening ventricular tachycardia.	1984-05-01	6711426
Cardiovascular responses to mianserin hydrochloride: a comparison with tricyclic antidepressant drugs.	1978	341940
Patterns of blood-pressure during chronic administration of postganglionic sympathetic blocking drugs for hypertension.	1976-11-13	62901
Exertional hypotension due to postganglionic sympathetic blocking drugs.	1976-08	981091
Dihydroergotamine: an effective treatment for postural hypotension due to antihypertensive drugs (ganglion-blocking agents excepted).	1976	135643
Factors predisposing to postural hypotensive symptoms in the treatment of high blood pressure.	1975-10	127594
Do antihypertensive drugs really cause depression?	1974-09	4431808
Side effects of hypotensive agents evaluated by a self-administered questionnaire.	1973-09-01	4726158

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 Created by `admin` on `Mon Mar 31 18:27:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:52 GMT 2025`
Record UNII	W8S3YM7AUU
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BETANIDINE

Preferred Name

English

BETHANIDINE

Common Name

English

BETHANIDINE [MI]

Common Name

English

GUANIDINE, N,N'-DIMETHYL-N''-(PHENYLMETHYL)-

Systematic Name

English

1-BENZYL-2,3-DIMETHYLGUANIDINE

Systematic Name

English

betanidine [INN]

Common Name

English

Betanidine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C02CC01