1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

• ChemBase编号: 450
• 分子式: C26H28N2
• 平均质量: 368.51392
• 单一同位素质量: 368.22524891
• SMILES: N1(CCN(CC1)CC=Cc1ccccc1)C(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)C=CCN1CCN(CC1)C(c1ccccc1)c1ccccc1
• 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
• InChIKey: DERZBLKQOCDDDZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine; 1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine; 1-(diphenylmethyl)-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine
• IUPAC传统名: cinnarizine; cinna; 1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine; 1-(diphenylmethyl)-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine
• 商标名: Abitrate; Aplactan; Aplexal; Apotomin; Artate; Carecin; Cerebolan; Cerepar; Cinaperazine; Cinazyn; Cinnacet; Cinnageron; Cinnarizine Stugeron; Corathiem; Denapol; Dimitron; Dimitronal; Eglen; Folcodal; Giganten; Glanil; Hilactan; Ixertol; Katoseran; Labyrin; Lazeta; Marisan; Midronal; Mitronal; Olamin; Processine; Sedatromin; Sepan; Siptazin; Spaderizine; Stugeron; Stutgeron; Stutgin; Toliman; Stugeron, Stunarone
• 别名: Cinnarizine; 1-trans-Cinnamyl-4-diphenylmethylpiperazine; Cinnarizine; 1-trans-Cinnamyl-4-diphenyl-methylpiperazine; Stugeron; 1-(Diphenylmethyl)-4-[(2Z)-3-phenyl-2-propen-1-yl]piperazine; (Z)-1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine; cis-Cinnarizine; (Z)-Cinnarizine; 1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine; Aplactan; Aplexal; Cerepar; Cinaperazine; Midronal; Mitronal; Olamin

登记号

• CAS号: 298-57-7; 750512-44-8
• EC号: 206-064-8
• MDL号: MFCD00056037
• PubChem SID: 46506769; 160963913; 24278320
• PubChem CID: 2761; 1547484
• CHEBI ID: 31403
• ATC码: N07CA02
• CHEMBL: 43064
• Chemspider ID: 1264793
• DrugBank ID: DB00568
• KEGG ID: D01295
• 美国药典/FDA物质标识码: 3DI2E1X18L
• 维基百科标题: Cinnarizine

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.0775893
• LogD (pH = 7.4): 4.841679
• Log P: 5.880391
• 摩尔折射率: 119.8648 cm^3
• 极化性: 46.581047 Å^3
• 极化表面积: 6.48 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.19
• LOG S: -5.33
• 溶解度: 1.72e-03 g/l

分子性质

理化性质

• 溶解度: 750 mg/L; Chloroform
• 外观: white powder; White Solid
• 熔点: 117-120°C
• 疏水性(logP): 5.3

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: TL3430000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 给药途径: Oral
• 半衰期: 3–4 h
• 妊娠期药物分类: C (US)
• 相关基因信息: human ... CACNA1A(773), DRD2(1813), HRH1(3269)
• 生物活性机理: Calcium antagonist; Histamine H 1 receptor antagonist; Reported catecholamine depletor; Reported inhibitor of bioenergetics of chromaffin granule ghosts; Reported Mg-atpase inhibitor; Reported Proton pump uncoupler; Reported to inhibit cardiac liposomal lipid peroxidation mediated by the xanthine oxidase system

产品相关信息

• 应用领域: Cerebral blood flow improver used for treatment of apoplexy and arteriosclerosis
• Empirical Formula (Hill Notation): C26H28N2

详细说明

MP Biomedicals - 02154986

(1-trans-Cinnamyl-4-diphenyl-methylpiperazine) Crystalline

DrugBank - DB00568

• Drug Groups: approved
• Description: Cinnarizine is an anti-histaminic drug which is mainly used for the control of vomiting due to motion sickness. Cinnarizine was first synthesized by Janssen Pharmaceutica in 1955.; ; It acts by interfering with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. The disparity of signal processing between inner ear motion receptors and the visual senses is abolished, so that the confusion of brain whether the individual is moving or standing is reduced. Vomiting in motion sickness is actually a physiological compensatory mechanism of the brain to keep the individual from moving so that it can adjust to the signal perception.; ; Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. It is also effectively combined with other nootropics, primarily piracetam; in such combination each drug potentiate the other in boosting brain oxygen supply.
• Indication: For the treatment of vertigo/meniere's disease, nausea and vomiting, motion sickness and also useful for vestibular symptoms of other origins.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - C5270

Biochem/physiol Actions
Ca2+ channel blocker; central and peripheral vasodilator.

Toronto Research Chemicals - C465300

Calcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic.

Toronto Research Chemicals - C465290

The Z-isomer of Cinnarizine (C465300).

参考文献

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• Spedding, M., et al.: Arch. Pharmacol., 318, 234 (1980)
• Morad, et al.: Pharmacol. Res., 35, 177 (1997)
• Barber, J.H., et al.: Pharmatherapeutica, 2, 401 (1980)
• Spedding, M., et al.: Arch. Pharmacol., 318, 234 (1980)
• Morad, et al.: Pharmacol. Res., 35, 177 (1997)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMR100; CMS125