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Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2
Molecular Weight 136.1946
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAHISTINE

SMILES

CNCCc1ccccn1

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.

Originator

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
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
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
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:
healthy, 20-31
n = 12
Health Status: healthy
Age Group: 20-31
Sex: M+F
Population Size: 12
Sources:
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:
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
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
Evaluation of betahistine for the prevention of seasickness: effect on vestibular function, psychomotor performance and efficacy at sea.
2003
[Comparative efficacy of betaserc and cinnarizine of vertigo in patients with migraine].
2003
Influence of 3 antivertiginous medications on the vigilance of healthy volunteers.
2003 Apr
Homeopathic vs conventional treatment of vertigo.
2003 Apr
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
Menière's disease.
2003 Jun
Double-blind, randomized, multicenter study comparing the effect of betahistine and flunarizine on the dizziness handicap in patients with recurrent vestibular vertigo.
2003 Jun
[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
Management of idiopathic sudden sensorineural hearing loss: experience in newly developing Qatar.
2004
[A use of betaserc in ataxic syndromes].
2004
[Pharmacological correction of cochleovestibular impairments].
2004
[The role of betaserk in combined treatment of neurosensory hypoacusis and vestibulopathy in childhood].
2004
Menière's disease.
2004 Jun
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
Plasticity of histamine H3 receptor expression and binding in the vestibular nuclei after labyrinthectomy in rat.
2004 Sep 10
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
Treatment of vertigo with a homeopathic complex remedy compared with usual treatments: a meta-analysis of clinical trials.
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
The effect of betahistine, a histamine H1 receptor agonist/H3 antagonist, on olanzapine-induced weight gain in first-episode schizophrenia patients.
2005 Mar
[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
[Betaserc in the treatment of vestibular dysfunctions of different etiology].
2006
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
Pharmacological advances in the treatment of neuro-otological and eye movement disorders.
2006 Feb
Role of H1 receptors in histamine-mediated up-regulation of STAT4 phosphorylation.
2006 Mar
[Current methods for diagnosis and treatment of iatrogenic ototoxicity].
2007
[Vestibular neuritis--a case description].
2007
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
[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
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
Case report: a case of intractable Meniere's disease treated with autogenic training.
2008 Jan 25
Patents

Sample Use Guides

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 [WHO-DD]
Common Name English
BETAHISTINE [MI]
Common Name English
NSC-42617
Code English
2-(2-(METHYLAMINO)ETHYL)PYRIDINE
Systematic Name English
HISTALEAN
Brand 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 Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
NCI_THESAURUS C29707
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
WHO-ATC N07CA01
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
Code System Code Type Description
WIKIPEDIA
BETAHISTINE
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
INN
1502
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
DRUG CENTRAL
346
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL24441
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
EPA CompTox
5638-76-6
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
MESH
D001621
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
227-086-4
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
CAS
5638-76-6
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
RXCUI
1511
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY RxNorm
EVMPD
SUB05794MIG
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
DRUG BANK
DB06698
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
FDA UNII
X32KK4201D
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
MERCK INDEX
M2450
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY Merck Index
PUBCHEM
2366
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY
NCI_THESAURUS
C83554
Created by admin on Sat Jun 26 02:06:30 UTC 2021 , Edited by admin on Sat Jun 26 02:06:30 UTC 2021
PRIMARY