기본 정보
- CAS
298-57-7- 표준 SMILES
C(=Cc1ccccc1)CN1CCN(C(c2ccccc2)c2ccccc2)CC1- InChIKey
DERZBLKQOCDDDZ-UHFFFAOYSA-N- 분자식
- C26H28N2
- 평균 분자량
- 368.5 g/mol
- 단동위원소 질량
- 368.2252489
개요
First synthesized by Janssen Pharmaceuticals in 1955, cinnarizine is an anti-histaminic drug mainly used for the control of vestibular disorders and motion sickness. Cinnarizine is a specific calcium channel blocker that primarily works on the central vestibular system to interfere with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. Combination use of cinnarizine with other nootropics, such as [piracetam] resulted in enhanced effect of boosting brain oxygen supply.
이름 및 식별자
- 우선 이름
- 1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
- IUPAC
- 1-benzhydryl-4-(3-phenylprop-2-enyl)piperazine
- 현지명
- 신나리진
- 영어명
- Stugeron
- 분자식
- C26H28N2
- 분자량
- 368.51
이름 및 동의어
1-(diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazineMFCD00056037CinnaC26H28N2Prestwick0_000278Prestwick1_0002781-benzhydryl-4-(3-phenylprop-2-enyl)piperazineOprea1_696883SCHEMBL44958SPBio_002375HMS3372L161-benzhydryl-4-cinnamyl-piperazine
이름 더 보기
신나리진CINNARIZINECinarizineCinnarizine, powderCinnarizine Hydrochlorider516516mdEglenR 516r1575Sepan
1-Cinnamyl-4-diphenylmethylpiperazineDB00568SY234515DB-047662C3459S47271-trans -Cinnamyl-4-diphenyl-methylpiperazineQ27224950
데이터베이스 식별자
- CAS
298-57-7- PubChem CID
- 2761
- DTXSID
DTXSID3022821
물성
구조 계산 물성
- XLogP
- 5.8
- 극성 표면적
- 6.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 429
실험 및 물리화학적 성질
DrugsPharmaceutical
LogP5.3
Solubility1.72e-03 g/L
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 117 · 117-120°C
- 끓는 점
- 488.83 °C · 488.83°C (rough estimate)
- 밀도
- 1.1818 · 1.1818 (rough estimate)
- 굴절률
- 1.762 · 1.7620 (estimate)
- 저장 조건
- 2 · Sealed in dry,2-8°C
- 용해도
- 50 mg/ml의 · 50mg/ml의 클로로포름에 용해됨
- 산도 계수 (pKa)
- 7.47 · pKa 7.47(H2O t=25.0 ) (Uncertain)
- 물리적 상태
- 가루
- 색상
- 하얀색
- 수용성
- 0.75 g/L · 0.75g/L(온도 미표시)
- Merck
- 14 · 14,2305
- InChI
- InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 2
- rtecs
- TL3430000
- 독성
- LD50 oral in rat: > 6500mg/kg
- HS 번호
- 2933.59.2100
- risk_code
- 20/22-36/37/38-42/43
- hazard_code
- Xn
- safety_code
- 22-24/25-36-26
- 기존화학 물질
- KE-12088
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Pharmacodynamics
Cinnarizine is an antihistamine and a calcium channel blocker. Histamines mediate a number of activities such as contraction of smooth muscle of the airways and gastrointestinal tract, vasodilatation, cardiac stimulation, secretion of gastric acid, promotion of interleukin release and chemotaxis of eosinophils and mast cells. Competitive antagonists at histamine H1 receptors may be divided into first (sedating) and second (non-sedating) generation agents. Some, such as Cinnarizine also block muscarinic acetylcholine receptors and are used as anti-emetic agents. Cinnarizine through its calcium channel blocking ability also inhibits stimulation of the vestibular system.
Mechanism of Action
Cinnarizine inhibits contractions of vascular smooth muscle cells by blocking L-type and T-type voltage gated calcium channels. Cinnarizine has also been implicated in binding to dopamine D2 receptors, histamine H1 receptors, and muscarinic acetylcholine receptors.
Cellular LocationsMembrane
Metabolite PathwaysCinnarizine H1-Antihistamine Action
응용 분야
용도Calcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic
일반 설명Cinnarizine is a piperazine derivative, which is extracted from wood reed roots. It exhibits antihistaminic and calcium antagonist property. Cinnarizine is used to treat vertigo, unsteadiness and cognitive disorders. Cinnarizine has anticholinergic, antiserotonergic and antidopaminergic effects. It enhances cerebral blood flow. Cinnarizine blocks the contraction of smooth muscles cells and also acts as a skin whitening agent.
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