Grundinformationen
- CAS
298-57-7- Standard-SMILES
C(=Cc1ccccc1)CN1CCN(C(c2ccccc2)c2ccccc2)CC1- InChIKey
DERZBLKQOCDDDZ-UHFFFAOYSA-N- Summenformel
- C26H28N2
- Durchschnittliche Molmasse
- 368,5 g/mol
- Monoisotopische Masse
- 368,2252489
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- 1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
- IUPAC
- 1-benzhydryl-4-(3-phenylprop-2-enyl)piperazine
- Lokaler Name
- Cinnarizin
- Englischer Name
- Stugeron
- Summenformel
- C26H28N2
- Molmasse
- 368.51
Namen und Synonyme
1-(diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazineMFCD00056037CinnaC26H28N2Prestwick0_000278Prestwick1_0002781-benzhydryl-4-(3-phenylprop-2-enyl)piperazineOprea1_696883SCHEMBL44958SPBio_002375HMS3372L161-benzhydryl-4-cinnamyl-piperazine
Weitere Namen anzeigen
CINNARIZINECinarizineCinnarizine, powderCinnarizine Hydrochlorider516516mdEglenR 516r1575Sepan
1-Cinnamyl-4-diphenylmethylpiperazineDB00568SY234515DB-047662C3459S47271-trans -Cinnamyl-4-diphenyl-methylpiperazineQ27224950
Datenbank-Bezeichner
- CAS
298-57-7- PubChem CID
- 2761
- DTXSID
DTXSID3022821
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,8
- Polarare Oberfläche (TPSA)
- 6,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 429
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceutical
LogP5.3
Solubility1.72e-03 g/L
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 117 · 117-120°C
- Siedepunkt
- 488.83 °C · 488.83°C (rough estimate)
- Dichte
- 1.1818 · 1.1818 (rough estimate)
- Brechungsindex
- 1.762 · 1.7620 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 50 mg/ml · Soluble in chloroform at 50mg/ml
- pka
- 7.47 · pKa 7.47(H2O t=25.0 ) (Uncertain)
- Aggregatzustand
- powder
- Farbe
- white
- Wasserlöslichkeit
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 2
- hs_code
- 2933.59.2100
- RTECS-Nr.
- TL3430000
- risk_code
- 20/22-36/37/38-42/43
- Toxizität
- LD50 oral in rat: > 6500mg/kg
- hazard_code
- Xn
- safety_code
- 22-24/25-36-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
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
Anwendungen
VerwendenCalcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic
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