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Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2
Molecular Weight 136.1943
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAHISTINE

SMILES

CNCCC1=CC=CC=N1

InChI

InChIKey=UUQMNUMQCIQDMZ-UHFFFAOYSA-N
InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3

HIDE SMILES / InChI
Molecular Formula C8H12N2
Molecular Weight 136.1943
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11700150 | https://www.ncbi.nlm.nih.gov/pubmed/18447604 | https://www.ncbi.nlm.nih.gov/pubmed/19300572

Betahistine is an orally administered, centrally acting histamine H1 receptor agonist with partial H3 antagonistic activity. It is proposed that betahistine may reduce peripherally the asymmetric functioning of the sensory vestibular organs in addition to increasing vestibulocochlear blood flow by antagonising local H3 heteroreceptors. Betahistine acts centrally by enhancing histamine synthesis within tuberomammillary nuclei of the posterior hypothalamus and histamine release within vestibular nuclei through antagonism of H3 autoreceptors. This mechanism, together with less specific effects of betahistine on alertness regulation through cerebral H1 receptors, should promote and facilitate central vestibular compensation. Betahistine is used to treat the symptoms associated with Ménière's disease, a condition of the inner ear which causes, vertigo (dizziness), tinnitus (ringing in the ears), hearing loss.

CNS Activity

Originator

Löffler, K.|Kirschner, M.
5
Sources: Löffler K, Kirschner M. Derivate des a-Picolyl-und a-Picolylmethyl-Alkins. Berichte der Deutschen Chemischen Gesellschaft 1905; 38: 3329-43
Curator's Comment: refrence retrieved from https://www.ncbi.nlm.nih.gov/pubmed/18447604

Approval Year

1966
59
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 31.0 µM [Ki]
Antagonist
2849
 6.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Betahistine

Approved Use

Betahistine is used to treat the symptoms associated with Ménière's disease, a condition of the inner ear which causes, vertigo (dizziness), tinnitus (ringing in the ears), hearing loss.

Launch Date

1968
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
339.4 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/14765546/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PYRIDINEACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1196 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/14765546/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PYRIDINEACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.17 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/14765546/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PYRIDINEACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
72 mg 3 times / day multiple, oral
Highest studied dose
Dose: 72 mg, 3 times / day
Route: oral
Route: multiple
Dose: 72 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1958439/
healthy, 20-31
Health Status: healthy
Age Group: 20-31
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1958439/
Sources:
https://pubmed.ncbi.nlm.nih.gov/1958439/
728 mg 1 times / day single, oral
Overdose
Dose: 728 mg, 1 times / day
Route: oral
Route: single
Dose: 728 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17061910/
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/17061910/
Sources:
https://pubmed.ncbi.nlm.nih.gov/17061910/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
110
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
150
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:35677
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:35677
ChemicalBook
CB4489793
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4489793
eMolecules
591762
https://www.emolecules.com/cgi-bin/more?vid=591762
MolPort
MolPort-000-142-007
https://www.molport.com/shop/molecule-link/MolPort-000-142-007
ZINC
ZINC000001675415
http://zinc15.docking.org/substances/ZINC000001675415
PubMed

PubMed

TitleDatePubMed
Management of Ménière's disease in general practice: adherence to the UK National Health Service 'Prodigy' guidelines.
2008-08
Reversible sensorineural hearing loss in a girl with Kawasaki disease.
2008-02-06
Treating common ear problems in pregnancy: what is safe?
2008-02
Case report: a case of intractable Meniere's disease treated with autogenic training.
2008-01-25
Improving the quality of life in patients with vestibular disorders: the role of medical treatments and physical rehabilitation.
2008-01
A fixed combination of cinnarizine/dimenhydrinate for the treatment of patients with acute vertigo due to vestibular disorders : a randomized, reference-controlled clinical study.
2008
Patient baseline characteristics in an open-label multinational study of betahistine in recurrent peripheral vestibular vertigo: the OSVaLD study.
2007-11
'Complementary ENT': a systematic review of commonly used supplements.
2007-08
Histaminergic ligands improve vestibular compensation in the cat: behavioural, neurochemical and molecular evidence.
2007-07-30
[Frequently occurring forms of dizziness and their treatment].
2007-05-21
Histamine affects STAT6 phosphorylation via its effects on IL-4 secretion: role of H1 receptors in the regulation of IL-4 production.
2007-03
[Current methods for diagnosis and treatment of iatrogenic ototoxicity].
2007
[Vestibular neuritis--a case description].
2007
Role of apolipoprotein E in anxiety.
2007
[Fluctuating deafness].
2006-12
[Treatment costs of otogenic vertigo].
2006-11-15
Restoration of vestibular function: basic aspects and practical advances for rehabilitation.
2006-09
Betahistine in the treatment of vertiginous syndromes: a meta-analysis.
2006-08
[Efficacy of Betahistine Mesilate combined with Flunarizine Hydrochloride for treating tinnitus].
2006-04
Betahistine increases ACh release from the cortex, but not histamine release from the nucleus basalis magnocellularis of freely-moving rats. 2. Histaminergic mechanisms in the CNS.
2006-04
[Assessment of betahistine dihydrochloride effectiveness in the treatment of vertigo of a different aetiology based on videonystagmography test results].
2006-03
Role of H1 receptors in histamine-mediated up-regulation of STAT4 phosphorylation.
2006-03
Pharmacological advances in the treatment of neuro-otological and eye movement disorders.
2006-02
[Assessment of betahistine dihydrochloride effectiveness in the treatment of disturbance of balance system, based on analysis of doctors and patients questionnaires results].
2006
[Clinical effectiveness of betahistine in monotherapy of vertigo for different etiology].
2006
[Betaserk in therapy of cochleovestibular disordes].
2006
Betahistine: a retrospective synopsis of safety data.
2006
[Betaserc in the treatment of vestibular dysfunctions of different etiology].
2006
Histamine (H3) receptors modulate the excitatory amino acid receptor response of the vestibular afferents.
2005-12-07
Menière's disease.
2005-12
Optimizing the pharmacological component of integrated balance therapy.
2005-11-15
[Vertigo attacks -- current therapy].
2005-11
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005-11
Dose- and duration-dependent effects of betahistine dihydrochloride treatment on histamine turnover in the cat.
2005-10-31
West Nile virus infection and conjunctival exposure.
2005-10
[A clinical study on the effect of Yinxing Damo combined with betahistine hydrochloride injection on vertebral basilar artery ischemic vertigo].
2005-09
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.
2005-07
Effects of betahistine on the spatiotemporal response properties of vestibulospinal neurons to labyrinthine volleys.
2005-05-16
Benign paroxysmal positional vertigo: a study of two manoeuvres with and without betahistine.
2005-04
A national survey amongst UK otolaryngologists regarding the treatment of Ménière's disease.
2005-02
Efficacy and Tolerability of a Fixed Combination of Cinnarizine and Dimenhydrinate versus Betahistine in the Treatment of Otogenic Vertigo : A Double-Blind, Randomised Clinical Study.
2005
[Clinico-neurological and stabilometric analysis of betahistine (betaserc) efficacy in the patients with vertigo in the rehabilitation period of ischemic stroke].
2005
[Efficacy of betaserk in experimental motor disease].
2005
[Epidemiology, clinical features and betaserc therapy of vertigo in initial and reversible cerebrovascular pathology].
2005
[Betaserk in the treatment of aftereffects of craniocerebral injury and vascular events].
2005
[Betaserc and improvement of life quality in war veterans].
2005
Meniere's disease.
2004-12
[Cerebral hemodynamics and statokinetic functions in patients with vertebral basilar vascular insufficiency].
2004
Betahistine in vertebrobasilar insufficiency.
2004
Investigation of Betaserc in auditory and vestibular disturbances.
2004
Patents

Patents

05189038
5
05854419
5
07186732
5

Sample Use Guides

In Vivo Use Guide
The usual dose is one tablet (16mg) or two tablets (8mg) three times a day, preferably taken with meals.
Route of Administration: Oral
In Vitro Use Guide
Treatment with dimaprit at 6 and 60 uM for 20 min significantly inhibited the anaphylactic histamine release, whereas betahistine at up to 80 uM under the same conditions did not affect it.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:03 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:03 GMT 2025
Record UNII
X32KK4201D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HISTALEAN
Preferred Name English
BETAHISTINE
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
N-METHYL-2-PYRIDINEETHANAMINE
Systematic Name English
BETAHISTINE [MART.]
Common Name English
BETAHISTINE [MI]
Common Name English
NSC-42617
Code English
2-(2-(METHYLAMINO)ETHYL)PYRIDINE
Systematic Name English
Betahistine [WHO-DD]
Common Name English
2-PYRIDINEETHANAMINE, N-METHYL-
Systematic Name English
betahistine [INN]
Common Name English
BETAHISTINE [VANDF]
Common Name English
BETAHISTINE MESILATE [JAN]
Common Name English
VESTIBO
Brand Name English
Classification Tree Code System Code
WHO-VATC QN07CA01
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
NCI_THESAURUS C29707
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
WHO-ATC N07CA01
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
Code System Code Type Description
WIKIPEDIA
BETAHISTINE
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
INN
1502
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
DRUG CENTRAL
346
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
ChEMBL
CHEMBL24441
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
SMS_ID
100000085867
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
EPA CompTox
DTXSID3022665
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
MESH
D001621
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-086-4
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
CAS
5638-76-6
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
RXCUI
1511
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY RxNorm
EVMPD
SUB05794MIG
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
DRUG BANK
DB06698
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
CHEBI
35677
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
FDA UNII
X32KK4201D
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
MERCK INDEX
m2450
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY Merck Index
PUBCHEM
2366
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
NCI_THESAURUS
C83554
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
NSC
42617
Created by admin on Mon Mar 31 17:49:03 GMT 2025 , Edited by admin on Mon Mar 31 17:49:03 GMT 2025
PRIMARY
Related Record Type Details
Structure of BETAHISTINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of BETAHISTINE MESILATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of 2-(2-PYRIDYL)ETHANOL
METABOLITE -> PARENT
Structure of 2-PYRIDINEACETIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of BETAHISTINE
ACTIVE MOIETY
NIH
NCATS
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