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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 83.3
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
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
- 용해도
- Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
- 산도 계수 (pKa)
- 3.46 · pKa 3.46 (Uncertain)
- 물리적 상태
- 기름
- 색상
- 밝은 노란색에서 노란색까지
- 수용성
- 1000 g/L · 1000g/L at 25℃
- Merck
- 13 · 13,1181
- InChI
- 1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
- InChIKey
- UUQMNUMQCIQDMZ-UHFFFAOYSA-N
- SMILES
- CNCCc1ccccn1
- LogP
- 0.68 · 0.68
- EPA
- 2 · 2-Pyridineethanamine, N-methyl- (5638-76-6)
안전 및 규제
GHS 분류
GHS Classification
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
독성 정보
Drug Induced Liver Injury
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
- safety_code
- 26-37/39
- 위험 참고 사항
- Corrosive
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 10 - Combustible liquids
화학 및 산업
약리 정보
ATC Code
N07CA01
N - Nervous system
QN - Nervous system
Mechanism of Action
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.
MeSH Pharmacological Classification
Drugs used to cause dilation of the blood vessels.
Drugs that bind to and activate histamine receptors. Although they have been suggested for a variety of clinical applications histamine agonists have so far been more widely used in research than therapeutically.
Absorption, Distribution and Excretion
When given orally, betahistine is rapidly and almost completely absorbed from the gastrointestinal tract. 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.[A220563,16388]
Betahistine is mainly excreted in the urine; with approximately 85-91% being detected in urine samples within 24 hours of administration.
In a pharmacokinetic study of rats, betahistine was found to be distributed throughout the body. Human data for betahistine's volume of distribution is not readily available.
용도 및 제조
응용 분야
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.
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