基本情報
- CAS
298-57-7- 標準SMILES
C(=Cc1ccccc1)CN1CCN(C(c2ccccc2)c2ccccc2)CC1- InChIKey
DERZBLKQOCDDDZ-UHFFFAOYSA-N- 分子式
- C26H28N2
- 平均分子量
- 368.5 g/mol
- 単同位体質量
- 368.2252489
概要
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.
名称と識別子
- 優先名称
- 1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
- IUPAC
- 1-benzhydryl-4-(3-phenylprop-2-enyl)piperazine
- 現地名
- シンナリジン
- 英語名
- Stugeron
- 分子式
- C26H28N2
- 分子量
- 368.51
名称と別名
1-(diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazineMFCD00056037CinnaC26H28N2Prestwick0_000278Prestwick1_0002781-benzhydryl-4-(3-phenylprop-2-enyl)piperazineOprea1_696883SCHEMBL44958SPBio_002375HMS3372L161-benzhydryl-4-cinnamyl-piperazine
名称をさらに表示
シンナリジン1-(ジフェニルメチル)-4-(3-フェニル-2-プロペニル)ピペラジン1-ベンズヒドリル-4-シンナミルピペラジンシンナリジン (JAN)1-(ジフェニルメチル)-4-(3-フェニルプロパ-2-エン-1-イル)ピペラジングラニルジミトロンスツットジンマリサン1-[3-フェニル-2-プロペニル]-4-ジフェニルメチルピペラジンセパンジミトロナールトリマンミトロナールホルコダールスツットゲロンラビリンミドロナールCINNARIZINECinarizineCinnarizine, powderCinnarizine Hydrochlorider516516mdEglenR 516
物性
構造計算による物性
- XLogP
- 5.8
- 極性表面積
- 6.5 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 6
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 429
実験および物理化学的性質
DrugsPharmaceutical
LogP5.3
Solubility1.72e-03 g/L
Physical DescriptionSolid
物理化学的性質
- 融点
- 117 · 117-120°C
- 沸点
- 488.83 °C · 488.83°C (rough estimate)
- 比重(密度)
- 1.1818 · 1.1818 (rough estimate)
- 屈折率
- 1.762 · 1.7620 (estimate)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 50 mg/mlでクロロホルムに可溶 · 50mg/mlでクロロホルムに可溶
- 酸解離定数(Pka)
- 7.47 · pKa 7.47(H2O t=25.0 ) (Uncertain)
- 外見
- 粉
- 色
- 白い
- 水溶解度
- 0.75 g/L · 0.75g/L(温度表記なし)
- 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
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- wgk
- 2
- rtecs
- TL3430000
- 毒性
- LD50 oral in rat: > 6500mg/kg
- hs_code
- 2933.59.2100
- risk_code
- 20/22-36/37/38-42/43
- 化審法
- (5)-960
- hazard_code
- Xn
- safety_code
- 22-24/25-36-26
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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
応用分野
使用Calcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic
一般的な説明Cinnarizine 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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上流原料
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