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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

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
2662
 31.0 µM [Ki]
Antagonist
2760
 6.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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

-5.14944E10
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
110
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
146
 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
Fixed combination of cinnarizine and dimenhydrinate versus betahistine dimesylate in the treatment of Ménière's disease: a randomized, double-blind, parallel group clinical study.
2002
Histamine receptor type coupled to nitric oxide-induced relaxation of guinea-pig nasal mucosa.
2002 Oct-Dec
Alternobaric oxygen therapy in long-term treatment of Ménière's disease.
2002 Winter
[Current approaches to the treatment of vertigo in children].
2003
[Comparative efficacy of betaserc and cinnarizine of vertigo in patients with migraine].
2003
LC-MS-MS analysis of 2-pyridylacetic acid, a major metabolite of betahistine: application to a pharmacokinetic study in healthy volunteers.
2003 Dec
[Vestibular migraine].
2003 Jan-Feb
Investigation of Betaserc in auditory and vestibular disturbances.
2004
Management of idiopathic sudden sensorineural hearing loss: experience in newly developing Qatar.
2004
[Pharmacological correction of cochleovestibular impairments].
2004
[Betaserc treatment of psychogenic vertigo].
2004
[The role of betaserk in combined treatment of neurosensory hypoacusis and vestibulopathy in childhood].
2004
Acute and clinically relevant drug-induced liver injury: a population based case-control study.
2004 Jul
Usefulness of high doses of glucocorticoids and hyperbaric oxygen therapy in sudden sensorineural hearing loss treatment.
2004 Nov
[Delirium in a 73-year-old man after many years of unwise use of betahistine].
2004 Nov 20
[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
Menière's disease.
2005 Dec
Histamine (H3) receptors modulate the excitatory amino acid receptor response of the vestibular afferents.
2005 Dec 7
[Vertigo attacks -- current therapy].
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
[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
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
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
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.
Name Type Language
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
HISTALEAN
Brand 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 Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
NCI_THESAURUS C29707
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
WHO-ATC N07CA01
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
Code System Code Type Description
WIKIPEDIA
BETAHISTINE
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
INN
1502
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
DRUG CENTRAL
346
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL24441
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
SMS_ID
100000085867
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022665
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
MESH
D001621
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-086-4
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
CAS
5638-76-6
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
RXCUI
1511
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY RxNorm
EVMPD
SUB05794MIG
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
DRUG BANK
DB06698
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
CHEBI
35677
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
FDA UNII
X32KK4201D
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
MERCK INDEX
M2450
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY Merck Index
PUBCHEM
2366
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
NCI_THESAURUS
C83554
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
NSC
42617
Created by admin on Wed Jul 05 22:42:15 UTC 2023 , Edited by admin on Wed Jul 05 22:42:15 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of BETAHISTINE
METABOLITE (PARENT)
Structure of 2-(2-PYRIDYL)ETHANOL
METABOLITE (PARENT)
Structure of 2-PYRIDINEACETIC ACID
SALT/SOLVATE (PARENT)
Structure of BETAHISTINE HYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of BETAHISTINE MESILATE
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