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Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2.2ClH
Molecular Weight 209.116
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAHISTINE HYDROCHLORIDE

SMILES

Cl.Cl.CNCCC1=CC=CC=N1

InChI

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

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
58
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 31.0 µM [Ki]
Antagonist
2778
 6.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
n = 12
Health Status: healthy
Age Group: 20-31
Sex: M+F
Population Size: 12
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
n = 1
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 1
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
111
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 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
MolPort
MolPort-000-142-007
https://www.molport.com/shop/molecule-link/MolPort-000-142-007
ZINC
ZINC000001675415
http://zinc15.docking.org/substances/ZINC000001675415
eMolecules
591762
https://www.emolecules.com/cgi-bin/more?vid=591762
PubMed

PubMed

TitleDatePubMed
[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
Meniere's disease.
2004 Dec
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
Benign paroxysmal positional vertigo: a study of two manoeuvres with and without betahistine.
2005 Apr
Menière's disease.
2005 Dec
Histamine (H3) receptors modulate the excitatory amino acid receptor response of the vestibular afferents.
2005 Dec 7
A national survey amongst UK otolaryngologists regarding the treatment of Ménière's disease.
2005 Feb
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.
2005 Jul
Effects of betahistine on the spatiotemporal response properties of vestibulospinal neurons to labyrinthine volleys.
2005 May 16
[Vertigo attacks -- current therapy].
2005 Nov
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
West Nile virus infection and conjunctival exposure.
2005 Oct
Dose- and duration-dependent effects of betahistine dihydrochloride treatment on histamine turnover in the cat.
2005 Oct 31
[A clinical study on the effect of Yinxing Damo combined with betahistine hydrochloride injection on vertebral basilar artery ischemic vertigo].
2005 Sep
[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
[Efficacy of Betahistine Mesilate combined with Flunarizine Hydrochloride for treating tinnitus].
2006 Apr
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 Apr
Betahistine in the treatment of vertiginous syndromes: a meta-analysis.
2006 Aug
[Fluctuating deafness].
2006 Dec
Pharmacological advances in the treatment of neuro-otological and eye movement disorders.
2006 Feb
[Assessment of betahistine dihydrochloride effectiveness in the treatment of vertigo of a different aetiology based on videonystagmography test results].
2006 Mar
Role of H1 receptors in histamine-mediated up-regulation of STAT4 phosphorylation.
2006 Mar
[Treatment costs of otogenic vertigo].
2006 Nov 15
Restoration of vestibular function: basic aspects and practical advances for rehabilitation.
2006 Sep
[Current methods for diagnosis and treatment of iatrogenic ototoxicity].
2007
[Vestibular neuritis--a case description].
2007
Role of apolipoprotein E in anxiety.
2007
'Complementary ENT': a systematic review of commonly used supplements.
2007 Aug
Optimizing the pharmacological component of integrated balance therapy.
2007 Jan-Feb
Histaminergic ligands improve vestibular compensation in the cat: behavioural, neurochemical and molecular evidence.
2007 Jul 30
Histamine affects STAT6 phosphorylation via its effects on IL-4 secretion: role of H1 receptors in the regulation of IL-4 production.
2007 Mar
[Frequently occurring forms of dizziness and their treatment].
2007 May 21
Patient baseline characteristics in an open-label multinational study of betahistine in recurrent peripheral vestibular vertigo: the OSVaLD study.
2007 Nov
Reversible sensorineural hearing loss in a girl with Kawasaki disease.
2007 Oct-Dec
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
Management of Ménière's disease in general practice: adherence to the UK National Health Service 'Prodigy' guidelines.
2008 Aug
Treating common ear problems in pregnancy: what is safe?
2008 Feb
Improving the quality of life in patients with vestibular disorders: the role of medical treatments and physical rehabilitation.
2008 Jan
Case report: a case of intractable Meniere's disease treated with autogenic training.
2008 Jan 25
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 Fri Dec 15 15:09:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:10 GMT 2023
Record UNII
49K58SMZ7U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAHISTINE HYDROCHLORIDE
MART.   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
BETAHISTINE HYDROCHLORIDE [MART.]
Common Name English
NSC-757397
Code English
BETAHISTINE DIHYDROCHLORIDE [MI]
Common Name English
BETAHISTINE HYDROCHLORIDE [VANDF]
Common Name English
PT-9
Code English
BETAHISTINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
BETAHISTINE HYDROCHLORIDE [USP-RS]
Common Name English
BETAHISTINE DIHYDROCHLORIDE
EP   MI  
Common Name English
BETAHISTINE DIHYDROCHLORIDE [EP MONOGRAPH]
Common Name English
2-[2-(Methylamino)ethyl]pyridine dihydrochloride
Systematic Name English
2-PYRIDINEETHANAMINE, N-METHYL-, DIHYDROCHLORIDE
Common Name English
BETAHISTINE HYDROCHLORIDE [USAN]
Common Name English
BETAHISTINE HCL
Common Name English
Betahistine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 247407
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
Code System Code Type Description
EVMPD
SUB00772MIG
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
DRUG BANK
DBSALT001190
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL24441
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
NCI_THESAURUS
C73794
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
EVMPD
SUB25919
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
CAS
5579-84-0
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1065618
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID10204355
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
FDA UNII
49K58SMZ7U
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
NSC
757397
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
SMS_ID
100000089998
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
226-966-5
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
MERCK INDEX
m2450
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY Merck Index
RXCUI
81964
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY RxNorm
PUBCHEM
68643
Created by admin on Fri Dec 15 15:09:10 GMT 2023 , Edited by admin on Fri Dec 15 15:09:10 GMT 2023
PRIMARY
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