Betahistine

HCID 2366CAS 5638-76-6

기본 정보

표준 SMILES
CNCCc1ccccn1
InChIKey
UUQMNUMQCIQDMZ-UHFFFAOYSA-N
분자식
C8H12N2
평균 분자량
136.19 g/mol
단동위원소 질량
136.10004838

개요

Betahistine is an aminoalkylpyridine that is pyridine substituted by a 2-(methylamino)ethyl group at position 2. It acts as a histamine agonist and a vasodilator, and is thought to improve the microcirculation of the labyrinth, resulting in reduced endolymphatic pressure. It is used (generally as the hydrochloride or mesylate salt) to reduce the symptoms of vertigo, tinnitus, and hearing loss associated with Mnire's disease. It has a role as a vasodilator agent and a H1-receptor agonist. It is an aminoalkylpyridine and a secondary amino compound.

이름 및 식별자

우선 이름
Betahistine
IUPAC
N-methyl-2-pyridin-2-ylethanamine
영어명
Betahistine
분자식
C8H12N2
분자량
136.19

이름 및 동의어

betahistine5638-76-6N-Methyl-2-pyridineethanamineVasomotal2-Pyridineethanamine, N-methyl-Betahistina2-[2-(Methylamino)ethyl]pyridineN-methyl-2-pyridin-2-ylethanamineBetahistinummethyl[2-(pyridin-2-yl)ethyl]amineBetaistina2-(2-(Methylamino)ethyl)pyridine
이름 더 보기
n-methyl-2-(pyridin-2-yl)ethan-1-amineY-G 14-d3PT 9 baseSerc baseβ-HistineNSC 42617-d3AKOS BBS-00002883Sinmenier (free base)
Vestibo(2-(2-Pyridyl)ethyl)methylamine[2-(2-Pyridyl)ethyl]methylamine2-(beta-Methylaminoethyl)pyridineHISTALEANX32KK4201DN-Methyl-2-(2-pyridinyl)ethanamineNSC-42617

데이터베이스 식별자

CAS
5638-76-6
PubChem CID
2366
DTXSID
DTXSID3022665
ChEMBL
CHEMBL24441
ChEBI
CHEBI:35677
UNII
X32KK4201D
EC Number
227-086-4
Nikkaji
J8.042J

물성

구조 계산 물성

XLogP
0.4
극성 표면적
24.9 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
10

실험 및 물리화학적 성질

Drugs · 3건

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP0.68
Boiling Point210.9±15.0 °C
Melting Point150-144
Physical DescriptionSolid
Dissociation Constants3.5, 9.7

물리화학적 성질

끓는 점
113 · 113-114 °C30 mm Hg(lit.)
밀도
0.984 g/mL · 0.984 g/mL at 25 °C(lit.)
증기압
17.7 Pa · 17.7Pa at 25℃
굴절률
20 · n20/D 1.518(lit.)
인화점
206 °F · 206 °F
저장 조건
Keep in dark place,Inert atmosphere,Room temperature

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationStatus: Active Update: 01-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18902
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

독성 정보

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

betahistine

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
UT5552000
HS 번호
2933399990
risk_code
36/37/38
hazard_code
Xi,C

화학 및 산업

약리 정보

ATC Code · 3건

N07CA01

N - Nervous system

QN - Nervous system

Protein BindingThe plasma protein binding of betahistine is reported to be less than 5%.
PharmacodynamicsThrough its actions on the histamine receptors, betahistine provides relief from vertigo associated with Ménière's disease.
Mechanism of Action · 2건

OBE101 is a H1 receptor agonist and partial H3 receptor antagonist. Because inhibition of H1 receptors increases feeding, agonism of H1 receptors by OBE101 should reduce feeding. By also partially antagonizing H3, OBE101 impedes a negative feedback loop that essentially prolongs stimulation of the H1 receptors.

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. 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. **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. 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. **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.

Biological Half-LifeThe half-life of betahistine is 3-4 hours.
Metabolism/MetabolitesBetahistine 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.

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >1000
General Manufacturing Information2-Pyridineethanamine, N-methyl-: INACTIVE
응용 분야 · 2건

개요Betahistine is an analogue of histamine with weak agonist properties at histamine H1 receptors and more potent antagonistic effects at histamine H3 receptors.This drug is broadly used worldwide, except for the USA, since it has not been approved by the US Food and Drug Administration. Betahistine is a structural analog of histamine that acts as a weak partial postsynaptic histamine H1 receptor agonist and presynaptic H3 receptor antagonist, with no effect on postsynaptic H2 receptors (Gbahou et al, 2010). The mechanism of action of the drug appears to depend mainly on its action on H3 receptors mediated by two metabolites, aminoethylpyridine and hydroxyethylpyridine (Bertich et al, 2014).

용도Betahistine is a vasodilator, a mild H1 histamine agonist, and a potent H3 histamine antagonist. The mechanism of action in Meniere's disease is unknown, but theories include reducing the endolymphatic pressure through improved circulation in the stria vascularis or inhibiting activity in the vestibular nuclei. It has been found to be a safe drug with a very low side effect profile. Betahistine was FDA approved for Meniere's disease in the US market for a short period of time in the 1970s, but approval was then rescinded due to lack of evidence supporting its efficacy. However, based on clinical experience and several observational studies, it is still widely used elsewhere in the world.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]

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