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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
SynonymLanguageCode
[2-(2-Pyridyl)ethyl]methylamineNot AvailableNot Available
2-(beta-Methylaminoethyl)pyridineNot AvailableNot Available
2-[2-(Methylamino)ethyl]pyridineNot AvailableNot Available
BetahistinaNot AvailableNot Available
BetahistinumNot AvailableNot Available
N-Methyl-2-(2-pyridinyl)ethanamineNot AvailableNot Available
N-Methyl-2-pyridineethanamineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
SercAbbott Products
Brand mixturesNot Available
Categories
CAS number5638-76-6
WeightAverage: 136.1943
Monoisotopic: 136.100048394
Chemical FormulaC8H12N2
InChI KeyUUQMNUMQCIQDMZ-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassNot Available
Direct parentPyridines and Derivatives
Alternative parentsPolyamines; Dialkylamines
Substituentspolyamine; secondary aliphatic amine; secondary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
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
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
Property Value Probability
Human Intestinal Absorption + 0.9949
Blood Brain Barrier + 0.9485
Caco-2 permeable + 0.7747
P-glycoprotein substrate Substrate 0.5736
P-glycoprotein inhibitor I Non-inhibitor 0.9568
P-glycoprotein inhibitor II Non-inhibitor 0.9843
Renal organic cation transporter Inhibitor 0.5858
CYP450 2C9 substrate Non-substrate 0.7936
CYP450 2D6 substrate Substrate 0.7703
CYP450 3A4 substrate Non-substrate 0.71
CYP450 1A2 substrate Non-inhibitor 0.6919
CYP450 2C9 substrate Non-inhibitor 0.9339
CYP450 2D6 substrate Non-inhibitor 0.9345
CYP450 2C19 substrate Non-inhibitor 0.9253
CYP450 3A4 substrate Non-inhibitor 0.8961
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9759
Ames test Non AMES toxic 0.8219
Carcinogenicity Non-carcinogens 0.9557
Biodegradation Not ready biodegradable 0.8351
Rat acute toxicity 1.3795 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8518
hERG inhibition (predictor II) Non-inhibitor 0.8184
Pharmacoeconomics
Manufacturers
  • Abbott products inc
  • Teva Pharmaceuticals
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral8mg, 16mg, 24mg
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 solubility4.93e+01 g/lALOGPS
logP0.59ALOGPS
logP0.63ChemAxon
logS-0.44ALOGPS
pKa (strongest basic)9.77ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area24.92ChemAxon
rotatable bond count3ChemAxon
refractivity41.33ChemAxon
polarizability15.85ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
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 Reference
  1. Health Canada
External Links
ResourceLink
KEGG DrugD07522
PubChem Compound2366
PubChem Substance99443252
ChemSpider2276
ChEBI35677
ChEMBLCHEMBL24441
PharmGKBPA165958372
WikipediaBetahistine
ATC CodesN07CA01
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Serc monograph. (2010). [Electronic version]. e-CPS. Retrieved November 28, 2010.
  2. Barak N: Betahistine: what’s new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. Pubmed
  3. 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

2. Histamine H3 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H3 receptor Q9Y5N1 Details

References:

  1. Barak N: Betahistine: what’s new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. Pubmed
  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
  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. Epub 2010 Jun 8. Pubmed

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Drug created on May 06, 2010 10:01 / Updated on September 16, 2013 18:04