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Identification
NameBetahistine
Accession NumberDB06698
TypeSmall Molecule
GroupsApproved
Description

Betahistine is an antivertigo drug first used for treating vertigo assosicated with Ménière’s disease. It is also commonly used for patients with balance disorders.

Structure
Thumb
Synonyms
[2-(2-Pyridyl)ethyl]methylamine
2-(beta-Methylaminoethyl)pyridine
2-[2-(Methylamino)ethyl]pyridine
Betahistina
Betahistinum
N-Methyl-2-(2-pyridinyl)ethanamine
N-Methyl-2-pyridineethanamine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Betahistinetablet24 mgoralActavis Pharma Company2011-10-13Not applicableCanada
Act Betahistinetablet16 mgoralActavis Pharma Company2011-10-13Not applicableCanada
Auro-betahistinetablet24 mgoralAuro Pharma Inc2015-11-30Not applicableCanada
Auro-betahistinetablet16 mgoralAuro Pharma Inc2015-11-30Not applicableCanada
Auro-betahistinetablet8 mgoralAuro Pharma Inc2015-11-30Not applicableCanada
PMS-betahistinetablet24 mgoralPharmascience Inc2014-01-16Not applicableCanada
PMS-betahistinetablet16 mgoralPharmascience Inc2014-01-16Not applicableCanada
Serctablet16 mgoralBgp Pharma Ulc2001-08-17Not applicableCanada
Serctablet24 mgoralBgp Pharma Ulc2003-12-10Not applicableCanada
Serc - Tab 4mgtablet4 mgoralSolvay Pharma Inc1997-08-132001-03-22Canada
Serc 4mgtablet4 mgoralUnimed Canada Inc.1968-12-311996-09-10Canada
Serc 8 mgtablet8 mgoralSolvay Pharma Inc1999-09-272005-02-07Canada
Teva-betahistinetablet24 mgoralTeva Canada Limited2006-08-30Not applicableCanada
Teva-betahistinetablet16 mgoralTeva Canada Limited2006-08-14Not applicableCanada
Teva-betahistinetablet8 mgoralTeva Canada Limited2010-12-13Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-betahistinetablet8 mgoralApotex IncNot applicableNot applicableCanada
Apo-betahistinetablet24 mgoralApotex IncNot applicableNot applicableCanada
Apo-betahistinetablet16 mgoralApotex IncNot applicableNot applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Betahistine hydrochloride
ThumbNot applicableDBSALT001190
Categories
UNIIX32KK4201D
CAS number5638-76-6
WeightAverage: 136.1943
Monoisotopic: 136.100048394
Chemical FormulaC8H12N2
InChI KeyInChIKey=UUQMNUMQCIQDMZ-UHFFFAOYSA-N
InChI
InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
IUPAC Name
methyl[2-(pyridin-2-yl)ethyl]amine
SMILES
CNCCC1=CC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the reduction of episodes of vertigo association with Ménière's disease.
PharmacodynamicsBetahistine primarily acts as a histamine H1-agonist with 0.07 times the activity of histamine. Stimulating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which results in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibular organs as well as by increasing vestibulocochlear blood flow. Doing so aids in decreasing symptoms of vertigo and balance disorders. Betahistine also acts as a histamine H3-receptor antagonist which causes an increased output of histamine from histaminergic nerve endings which can further increase the direct H1-agonist activity. Furthermore, H3-receptor antagonism increases the levels of neurotransmitters such as serotonin in the brainstem, which inhibits the activity of vestibular nuclei, helping to restore proper balance and decrease in vertigo symptoms.
Mechanism of actionNot Available
Related Articles
AbsorptionWhen given orally, betahistine is rapidly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingVery low.
Metabolism

Betahistine is metabolized primarily into 2-pyridylacetic acid and is subsequently excreted in the urine.

SubstrateEnzymesProduct
Betahistine
Not Available
2-pyridylacetic acidDetails
Route of eliminationRenal
Half life3-4 hours
ClearanceNot Available
ToxicitySymptoms of overdose (< 640 mg) include mild to moderate nausea, dry mouth, dyspepsia, abdominal pain and somnolence. More serious complications such as convulsions, pulmonary or cardiac complications, may occur with higher intentional overdoses (> 640 mg).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.9485
Caco-2 permeable+0.7747
P-glycoprotein substrateSubstrate0.5736
P-glycoprotein inhibitor INon-inhibitor0.9568
P-glycoprotein inhibitor IINon-inhibitor0.9843
Renal organic cation transporterInhibitor0.5858
CYP450 2C9 substrateNon-substrate0.7936
CYP450 2D6 substrateSubstrate0.7703
CYP450 3A4 substrateNon-substrate0.71
CYP450 1A2 substrateNon-inhibitor0.6919
CYP450 2C9 inhibitorNon-inhibitor0.9339
CYP450 2D6 inhibitorNon-inhibitor0.9345
CYP450 2C19 inhibitorNon-inhibitor0.9253
CYP450 3A4 inhibitorNon-inhibitor0.8961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9759
Ames testNon AMES toxic0.8219
CarcinogenicityNon-carcinogens0.9557
BiodegradationNot ready biodegradable0.8351
Rat acute toxicity1.3795 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8518
hERG inhibition (predictor II)Non-inhibitor0.8184
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral16 mg
Tabletoral24 mg
Tabletoral4 mg
Tabletoral8 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.68YOUNG,RC ET AL. (1993)
pKa10.1 (at 10 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility49.3 mg/mLALOGPS
logP0.59ALOGPS
logP0.63ChemAxon
logS-0.44ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.33 m3·mol-1ChemAxon
Polarizability15.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Jean S. Cherqui, Alain C. Djiane, “New galenical form of administration of betahistine and its derivatives and the preparation thereof.” U.S. Patent US4264574, issued February, 1979.

US4264574
General ReferencesNot Available
External Links
ATC CodesN07CA01
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ArformoterolThe therapeutic efficacy of Arformoterol can be decreased when used in combination with Betahistine.
AzelastineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Azelastine.
BrompheniramineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Brompheniramine.
CarbinoxamineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Carbinoxamine.
CetirizineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Cetirizine.
ChlorphenamineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Chlorphenamine.
ClemastineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Clemastine.
CyclizineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Cyclizine.
CyproheptadineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Cyproheptadine.
DesloratadineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Desloratadine.
Dexchlorpheniramine maleateThe therapeutic efficacy of Betahistine can be decreased when used in combination with Dexchlorpheniramine maleate.
DimenhydrinateThe therapeutic efficacy of Betahistine can be decreased when used in combination with Dimenhydrinate.
DiphenhydramineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Diphenhydramine.
DoxylamineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Doxylamine.
FexofenadineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Fexofenadine.
FormoterolThe therapeutic efficacy of Formoterol can be decreased when used in combination with Betahistine.
HydroxyzineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Hydroxyzine.
IndacaterolThe therapeutic efficacy of Indacaterol can be decreased when used in combination with Betahistine.
IsocarboxazidThe serum concentration of Betahistine can be increased when it is combined with Isocarboxazid.
LevocetirizineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Levocetirizine.
LinezolidThe serum concentration of Betahistine can be increased when it is combined with Linezolid.
LoratadineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Loratadine.
MeclizineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Meclizine.
MoclobemideThe serum concentration of Betahistine can be increased when it is combined with Moclobemide.
OlodaterolThe therapeutic efficacy of Olodaterol can be decreased when used in combination with Betahistine.
OlopatadineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Olopatadine.
OrciprenalineThe therapeutic efficacy of Orciprenaline can be decreased when used in combination with Betahistine.
PhenelzineThe serum concentration of Betahistine can be increased when it is combined with Phenelzine.
PirbuterolThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Betahistine.
PizotifenThe therapeutic efficacy of Betahistine can be decreased when used in combination with Pizotifen.
ProcarbazineThe serum concentration of Betahistine can be increased when it is combined with Procarbazine.
RasagilineThe serum concentration of Betahistine can be increased when it is combined with Rasagiline.
SalbutamolThe therapeutic efficacy of Salbutamol can be decreased when used in combination with Betahistine.
SalmeterolThe therapeutic efficacy of Salmeterol can be decreased when used in combination with Betahistine.
SelegilineThe serum concentration of Betahistine can be increased when it is combined with Selegiline.
Tedizolid PhosphateThe serum concentration of Betahistine can be increased when it is combined with Tedizolid Phosphate.
TerbutalineThe therapeutic efficacy of Terbutaline can be decreased when used in combination with Betahistine.
TranylcypromineThe serum concentration of Betahistine can be increased when it is combined with Tranylcypromine.
TriprolidineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Triprolidine.
Food Interactions
  • Take with food.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Histamine receptor activity
Specific Function:
The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive activity (spontaneous activity in the absence of agonist). Agonist stimulation of isoform 3 neither modified adenylate cyclase activity nor induced intracellular calcium mobilization.
Gene Name:
HRH3
Uniprot ID:
Q9Y5N1
Molecular Weight:
48670.81 Da
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]
  3. Gbahou F, Davenas E, Morisset S, Arrang JM: Effects of betahistine at histamine H3 receptors: mixed inverse agonism/agonism in vitro and partial inverse agonism in vivo. J Pharmacol Exp Ther. 2010 Sep 1;334(3):945-54. doi: 10.1124/jpet.110.168633. Epub 2010 Jun 8. [PubMed:20530654 ]
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Drug created on May 06, 2010 10:01 / Updated on September 16, 2013 18:04