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Identification
- Summary
Betahistine is an antivertigo agent used for the reduction of episodes of vertigo association with Ménière's disease.
- Brand Names
- Serc
- Generic Name
- Betahistine
- DrugBank Accession Number
- DB06698
- Background
Ménière's disease is a progressive disease of the inner ear characterized by vertigo, tinnitus, and hearing loss. It has a significant impact on both the physical and social functioning of affected individuals.2,13
Betahistine is a histamine-like antivertigo drug used for treating symptoms associated with Ménière's disease. It is thought to reduce symptoms through its actions on histamine receptors.4,12 Betahistine was first approved by the FDA in the 1970s but withdrawn within approximately 5 years due to a lack of evidence supporting its efficacy. It is currently marketed in Canada by various companies, including Teva Pharmaceuticals.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Betahistine (DB06698)
- Weight
- Average: 136.1943
Monoisotopic: 136.100048394 - Chemical Formula
- C8H12N2
- Synonyms
- [2-(2-pyridyl)ethyl]methylamine
- 2-(β-methylaminoethyl)pyridine
- 2-[2-(methylamino)ethyl]pyridine
- Betahistina
- Bétahistine
- Betahistine
- Betahistinum
- N-methyl-2-(2-pyridinyl)ethanamine
- N-methyl-2-pyridineethanamine
Pharmacology
- Indication
Betahistine is indicated for the reduction of recurrent vertigo episodes associated with Ménière's disease in patients 18 years old and above.11
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Meniere's disease •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Through its actions on the histamine receptors, betahistine provides relief from vertigo associated with Ménière's disease.3,5,11
- Mechanism of action
Vertigo is a disturbing sensation of movement caused by dysfunction of the labyrinth (inner ear), vestibular nerve, cerebellum, brainstem, or Central Nervous System (CNS). Vestibular forms of vertigo are often accompanied by auditory dysfunctions such as hyperacusis, hearing loss, and tinnitus.3 In most cases, adaptive mechanisms of the CNS lead to functional recovery after episodes of vertigo, however, syndromes such as Ménière's disease tend to cause the recurrence of vertigo symptoms. This significantly impacts the quality of life and the ability to carry out daily activities.2
H1-receptor activity
The mechanism of action of betahistine is multifactorial. Ménière's disease is thought to result from a disruption of endolymphatic fluid homeostasis in the ear.6 Betahistine mainly acts as a histamine H1-receptor agonist. The stimulation of H1-receptors in the inner ear causes a vasodilatory effect leading to increased permeability of blood vessels and a reduction in endolymphatic pressure; this action prevents the rupture of the labyrinth, which can contribute to the hearing loss associated with Ménière's disease. Betahistine is also purported to act by reducing the asymmetrical functioning of sensory vestibular organs and increasing vestibulocochlear blood flow, relieving symptoms of vertigo.5
H3-receptor activity
In addition to the above mechanisms, betahistine also acts as a histamine H3-receptor antagonist, increasing the turnover of histamine from postsynaptic histaminergic nerve receptors, subsequently leading to an increase in H1-agonist activity. H3-receptor antagonism elevates levels of neurotransmitters including serotonin in the brainstem, inhibiting the activity of vestibular nuclei, thus restoring proper balance and decreasing vertigo symptoms.3
Target Actions Organism AHistamine H1 receptor agonistHumans AHistamine H3 receptor antagonistHumans - Absorption
When given orally, betahistine is rapidly and almost completely absorbed from the gastrointestinal tract.6,11 In the fasted state, Cmax is achieved within 1 hour of administration; in the fed state, Cmax is delayed, but the total drug absorption is similar. Food, therefore, has little effect on the absorption of betahistine.9
- Volume of distribution
In a pharmacokinetic study of rats, betahistine was found to be distributed throughout the body.14 Human data for betahistine's volume of distribution is not readily available.6,9,11,14
- Protein binding
The plasma protein binding of betahistine is reported to be less than 5%.9,11
- Metabolism
Betahistine is metabolized primarily into the inactive metabolite 2-pyridylacetic acid. There is both clinical and in vitro evidence that monoamine oxidase enzymes are responsible for the metabolism of betahistine.10,8,7,11
Hover over products below to view reaction partners
- Route of elimination
Betahistine is mainly excreted in the urine; with approximately 85-91% being detected in urine samples within 24 hours of administration.6,9,11
- Half-life
- Clearance
Not Available
- Adverse Effects
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Symptoms of an overdose with betahistine (< 640 mg) include dry mouth, nausea, dyspepsia, abdominal pain, and somnolence. Serious complications such as convulsions, pulmonary or cardiac effects may occur with higher doses (> 640 mg), especially during intentional overdoses and combination with other drugs. In the case of an overdose with betahistine, provide supportive therapy, and contact the local poison control center for further management.11
- Pathways
Pathway Category Betahistine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The therapeutic efficacy of Betahistine can be decreased when used in combination with Acrivastine. Albuterol The therapeutic efficacy of Salbutamol can be decreased when used in combination with Betahistine. Alimemazine The therapeutic efficacy of Betahistine can be decreased when used in combination with Alimemazine. Amitriptyline The therapeutic efficacy of Betahistine can be decreased when used in combination with Amitriptyline. Amoxapine The therapeutic efficacy of Betahistine can be decreased when used in combination with Amoxapine. - Food Interactions
- Take with food. This may reduce or prevent gastrointestinal upset.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Betahistine hydrochloride 49K58SMZ7U 5579-84-0 XVDFMHARQUBJRE-UHFFFAOYSA-N Betahistine maleate U5SU5350VT 133206-34-5 JLPICNMNXPSXMA-BTJKTKAUSA-N Betahistine mesylate X1L0E3R43Y 54856-23-4 ZBJJDYGJCNTNTH-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Betahistine Tablet 24 mg Oral Actavis Pharma Company 2011-10-13 2018-06-12 Canada 
Act Betahistine Tablet 16 mg Oral Actavis Pharma Company 2011-10-13 2018-06-12 Canada Betahistine Tablet 8 mg Oral Surax Healthcare Inc Not applicable Not applicable Canada Betahistine Tablet 16 mg Oral Sanis Health Inc 2018-03-07 Not applicable Canada Betahistine Tablet 24 mg Oral Surax Healthcare Inc Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-betahistine Tablet 16 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-betahistine Tablet 8 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-betahistine Tablet 24 mg Oral Apotex Corporation Not applicable Not applicable Canada Auro-betahistine Tablet 16 mg Oral Auro Pharma Inc 2015-11-30 Not applicable Canada Auro-betahistine Tablet 8 mg Oral Auro Pharma Inc 2015-11-30 Not applicable Canada
Categories
- ATC Codes
- N07CA01 — Betahistine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Pyridines and derivatives / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organoheterocyclic compound / Organopnictogen compound / Pyridine / Secondary aliphatic amine / Secondary amine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- secondary amino compound, aminoalkylpyridine (CHEBI:35677)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- X32KK4201D
- CAS number
- 5638-76-6
- InChI Key
- 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
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 References
- Murdin L, Hussain K, Schilder AG: Betahistine for symptoms of vertigo. Cochrane Database Syst Rev. 2016 Jun 21;(6):CD010696. doi: 10.1002/14651858.CD010696.pub2. [Article]
- Orji F: The Influence of Psychological Factors in Meniere's Disease. Ann Med Health Sci Res. 2014 Jan;4(1):3-7. doi: 10.4103/2141-9248.126601. [Article]
- Della Pepa C, Guidetti G, Eandi M: Betahistine in the treatment of vertiginous syndromes: a meta-analysis. Acta Otorhinolaryngol Ital. 2006 Aug;26(4):208-15. [Article]
- Parfenov VA, Golyk VA, Matsnev EI, Morozova SV, Melnikov OA, Antonenko LM, Sigaleva EE, Situkho MI, Asaulenko OI, Popovych VI, Zamergrad MV: Effectiveness of betahistine (48 mg/day) in patients with vestibular vertigo during routine practice: The VIRTUOSO study. PLoS One. 2017 Mar 30;12(3):e0174114. doi: 10.1371/journal.pone.0174114. eCollection 2017. [Article]
- Lacour M, van de Heyning PH, Novotny M, Tighilet B: Betahistine in the treatment of Meniere's disease. Neuropsychiatr Dis Treat. 2007 Aug;3(4):429-40. [Article]
- Duaa J. Al-Tamimi, Afaq M. Ammoo , Mays E. Alani, Jaafar J. Ibraheem, Duaa J. Al-Tamimi , Afaq M. Ammoo , Mays E. Alani and Jaafar J. Ibraheem: Pharmacokinetics and dose proportionality of betahistine in healthy individuals Scientia Pharmaceutica. [Article]
- Strupp M, Kraus L, Schautzer F, Rujescu D: Meniere's disease: combined pharmacotherapy with betahistine and the MAO-B inhibitor selegiline-an observational study. J Neurol. 2018 Mar 12. pii: 10.1007/s00415-018-8809-8. doi: 10.1007/s00415-018-8809-8. [Article]
- Sternson LA, Tobia AJ, Walsh GM, Sternson AW: The metabolism of betahistine in the rat. Drug Metab Dispos. 1974 Mar-Apr;2(2):123-8. [Article]
- Ramos Alcocer R, Ledezma Rodriguez JG, Navas Romero A, Cardenas Nunez JL, Rodriguez Montoya V, Deschamps JJ, Liviac Ticse JA: Use of betahistine in the treatment of peripheral vertigo. Acta Otolaryngol. 2015;135(12):1205-11. doi: 10.3109/00016489.2015.1072873. Epub 2015 Aug 6. [Article]
- Val L, Chen LS, Mendes GD, De Nucci G: Comparative bioavailability of betahistine tablet formulations administered in healthy subjects. Arzneimittelforschung. 2010;60(7):440-4. doi: 10.1055/s-0031-1296309. [Article]
- Product Monograph: SERC (betahistine hydrochloride) oral tablets [Link]
- Medicines UK: Betahistine Dihydrochloride 16mg Tablets [Link]
- NIH StatPearls: Meniere's disease [Link]
- Product monograph: SERC † (Betahistine dihydrochloride) 8 mg, 16 mg, and 24 mg oral tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0015644
- KEGG Drug
- D07522
- PubChem Compound
- 2366
- PubChem Substance
- 99443252
- ChemSpider
- 2276
- BindingDB
- 96589
- 1511
- ChEBI
- 35677
- ChEMBL
- CHEMBL24441
- ZINC
- ZINC000001675415
- PharmGKB
- PA165958372
- Wikipedia
- Betahistine
- MSDS
- Download (24.2 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Menière's Disease 1 somestatus stop reason just information to hide Not Available Completed Prevention Nausea and vomiting 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Benign Paroxysmal Positional Vertigo (BPPV) 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Cervicogenic Dizziness 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Vestibular Disorders 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 8.000 mg Solution Oral Tablet Oral 5 mg/1 Tablet Oral 2.5 mg/1 Tablet, coated Oral 1600000 mg Tablet, coated Oral 8 mg Tablet Oral 1600000 mg Tablet Oral 2400000 mg Tablet, film coated Oral 800000 mg Tablet Oral 15.6 mg/1 Tablet Oral 24 mg Tablet, orally disintegrating Oral 24 mg Tablet Oral 24.00 mg Tablet Oral 800000 mg Tablet Oral 24.000 mg Tablet, orally disintegrating Oral 8 Mg Tablet, extended release Oral 12 MG Solution / drops Oral Tablet, orally disintegrating Oral 12 MG Tablet, orally disintegrating Oral 6 MG Tablet Oral 16.000 mg Tablet Oral 4 mg / tab Tablet Oral 8 mg / tab Tablet, film coated Oral 8 mg Solution Oral 8 mg Tablet Oral Solution / drops Oral 8 MG/ML Tablet, coated Oral 24 mg Solution Oral 12.5 mg Tablet, film coated Oral 16 mg Tablet Oral 8 mg Tablet Oral 16 mg Tablet, film coated Oral 24 mg Tablet Oral 12 mg Tablet Oral 6 mg Tablet, coated Oral 16 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 150-144 https://www.chembk.com/en/chem/Betahistine%20Hydrochloride boiling point (°C) 210.9±15.0 °C https://www.chemsrc.com/en/cas/5638-76-6_951490.html logP 0.10 https://www.chemsrc.com/en/cas/5638-76-6_951490.html pKa 3.5, 9.7 https://www.mylan.ca/-/media/mylanca/documents/english/product-pdf/pdfs-dec-2015/serc-pm-2016.01.08.pdf?la=en-ca - Predicted Properties
Property Value Source Water Solubility 49.3 mg/mL ALOGPS logP 0.59 ALOGPS logP 0.63 Chemaxon logS -0.44 ALOGPS pKa (Strongest Basic) 9.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 24.92 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 41.33 m3·mol-1 Chemaxon Polarizability 15.85 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9339 CYP450 2D6 inhibitor Non-inhibitor 0.9345 CYP450 2C19 inhibitor Non-inhibitor 0.9253 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9200000000-7632c62aa4558c2fb7dd Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-1900000000-b19f0cc268fedb478d3f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0zg0-0900000000-a6c7b960d6cb6baf621e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9800000000-6d0f9d07513ec0395eaa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0550-5900000000-382968ebc2cb97b69ea6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-1ba90537111cba7f5989 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01ox-9200000000-eaef90ea4b7a650e83e0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.4833663 predictedDarkChem Lite v0.1.0 [M-H]- 125.31677 predictedDeepCCS 1.0 (2019) [M+H]+ 131.7084663 predictedDarkChem Lite v0.1.0 [M+H]+ 128.09433 predictedDeepCCS 1.0 (2019) [M+Na]+ 131.2213663 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.60133 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- 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 . [Article]
- Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [Article]
- Lacour M, van de Heyning PH, Novotny M, Tighilet B: Betahistine in the treatment of Meniere's disease. Neuropsychiatr Dis Treat. 2007 Aug;3(4):429-40. [Article]
- Product Monograph: SERC (betahistine hydrochloride) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- HRH3
- Uniprot ID
- Q9Y5N1
- Uniprot Name
- Histamine H3 receptor
- Molecular Weight
- 48670.81 Da
References
- 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 . [Article]
- Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [Article]
- 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. [Article]
- Lacour M, van de Heyning PH, Novotny M, Tighilet B: Betahistine in the treatment of Meniere's disease. Neuropsychiatr Dis Treat. 2007 Aug;3(4):429-40. [Article]
- Product Monograph: SERC (betahistine hydrochloride) oral tablets [Link]
Enzymes
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
- Specific Function
- aliphatic amine oxidase activity
Components:
References
Drug created at May 06, 2010 16:01 / Updated at November 01, 2024 00:04