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

• ChemBase ID: 450
• Molecular Formular: C26H28N2
• Molecular Mass: 368.51392
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: cinnarizine; cinna; 1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine; 1-(diphenylmethyl)-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine
• Brand Name: 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
• Synonyms: 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

Database IDs

• CAS Number: 298-57-7; 750512-44-8
• EC Number: 206-064-8
• MDL Number: MFCD00056037
• PubChem SID: 46506769; 160963913; 24278320
• PubChem CID: 2761; 1547484
• CHEBI ID: 31403
• ATC CODE: N07CA02
• CHEMBL: 43064
• Chemspider ID: 1264793
• DrugBank ID: DB00568
• KEGG ID: D01295
• Unique Ingredient Identifier: 3DI2E1X18L
• Wikipedia Title: Cinnarizine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0775893
• LogD (pH = 7.4): 4.841679
• Log P: 5.880391
• Molar Refractivity: 119.8648 cm^3
• Polarizability: 46.581047 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.19
• LOG S: -5.33
• Solubility (Water): 1.72e-03 g/l

PROPERTIES

Physical Property

• Solubility: 750 mg/L; Chloroform
• Apperance: white powder; White Solid
• Melting Point: 117-120°C
• Hydrophobicity(logP): 5.3

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: TL3430000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 3–4 h
• Pregnancy Category: C (US)
• Gene Information: human ... CACNA1A(773), DRD2(1813), HRH1(3269)
• Mechanism of Action: 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

Product Information

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

DETAILS

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).

REFERENCES

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• 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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