Tiagabine hydrochloride

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H225：Flüssigkeit und Dampf leicht entzündbar.

  H370：Schädigt die Organe.

• Sicherheit

  P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

  P260：Dampf/Aerosol/Nebel nicht einatmen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P310：BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P311：GIFTINFORMATIONSZENTRUM/Arzt anrufen.

Tiagabine hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

• Beschreibung

  Tiagabine (145821-59-6) is a clinically useful anticonvulsant.1?It is also used to treat anxiety/panic disorder2?and neuropathic pain3. Tiagabine inhibits GABA-reuptake (IC50?[3H]GABA uptake = 67 nM)?via?inhibiting GABA transporter 1(GAT1) blocking both neuronal and glial GABA re-uptake.4,5

• Chemische Eigenschaften

  White to Off-White Solid

• Originator

  Gabitril,Cephalon, Inc.,USA

• Verwenden

  A GABA uptake inhibitor. Anticonvulsant.

• Verwenden

  Tiagabine hydrochloride was used to study serotoninergic transmission in G1 cells. It has also been used to study its anti-aging effects on the sensory neurons of C. elegans.

• Verwenden

  Tiagabine Hydrochloride is a GABA uptake inhibitor and an anticonvulsant (1,2,3). It is used to treat epilepsy, anxiety disorders, and panic disorder. Neuroprotective & Neuroresearch Product.

• Definition

  ChEBI: A hydrochloride resulting from the reaction of equimolar amounts of tiagabine and hydrogen chloride. A GABA reuptake inhibitor, it is used for the treatment of epilepsy.

• Manufacturing Process

  A solution of 34 ml of n-butyl lithium in 30 ml of anhydrous ether was cooled to -65°C under nitrogen and 5.3 ml of 3-methyl-2-bromothiophene in 10 ml anhydrous ether was added dropwise over a period of 10 min. The reaction mixture was stirred at -65°C for 1 h and 2.7 ml of ethyl 4-bromo-butyrate in 10 ml of anhydrous ether was added slowly. The reaction was stirred for 4 h while the temperature raised to -20°C, 20 ml water was added, and the mixture was stirred for 5 min after which the aqueous layer was removed. The ether layer was washed with 20 ml of water, and the combined aqueous phases were extracted with 50 ml of ether. The combined organic phases were dried over anhydrous sodium sulfate, which after evaporation yielded 9 g of 1- bromo-4,4-bis(3-methylthien-2-yl)but-3-ene as an oil. This compound was without further purification used for coupling with ethyl nipecotate.
  A suspension of 5.0 g of 1-bromo-4,4-bis(3-methylthien-2-yl)but-3-ene, 3.4 g of nipecotic acid ethyl ester and 3.3 g of potassium carbonate in 150 ml of dry acetone was kept under reflux for 15 h. The reaction mixture was evaporated and, after addition of 30 ml of water, the resulting solution was extracted twice with 50 ml of ethyl acetate. The ethyl acetate extracts were dried and evaporated leaving 7.3 g of an oil. By column chromatography on silica gel using methanol as eluent, N-(4,4-bis(3-methylthien-2-yl)but-3-enyl)nipecotic acid ethyl ester was isolated.
  5.3 g of N-(4,4-bis(3-methylthien-2-yl)but-3-enyl)nipecotic acid ethyl ester was dissolved in 100 ml of ethanol and 200 ml of an 8 N sodium hydroxide solution was added. The mixture was heated at reflux for 1 h, cooled and acidified by adding 10% hydrochloric acid. The resulting solution was evaporated and 100 ml of water was added to the residue. The resulting acid solution was extracted with ethyl acetate and the dried extract was evaporated to give (R)-N-(4,4-bis(3-methylthien-2-yl)but-3-enyl)nipecotic acid hydrochloride, melting point 187°-189°C.

• Therapeutic Function

  Antiepileptic

• Biochem/physiol Actions

  Tiagabine increases the synaptic GABA and enhances the neuronal inhibition. It is effective as adjunctive treatment of epilepsy and anxiety disorders.

• Lager

  Room temperature (desiccate)

• Einzelnachweise

  1) Schacter (1999)?A Review of the Antiepileptic Drug Tiagabine, Clin. Neuropharmacol.?22?312 2) Schwartz and Nihalani (2006)?Tiagabine in anxiety disorders, Expert Opin. Pharmacother.?7?1977 3) Novak?et al.?(2001)?Treatment of Painful Sensory Neuropathy With Tiagabine: A Pilot Study, Clin. Auton. Res.?11?357 4) Braestrup?et al.?(1990)?(R)-N-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl)nipecotic Acid Binds With High Affinity to the Brain Gamma-Aminobutyric Acid Uptake Carrier, J. Neurochem. 54 639 5) Nielsen?et al.?(1991)?Characterization of Tiagabine (NO-328), a New Potent and Selective GABA Uptake Inhibitor, Eur. J. Pharmacol.?196?257

Tiagabine hydrochloride Upstream-Materialien And Downstream Produkte

Tiagabine hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(174)Suppliers

145821-59-6, Tiagabine hydrochloride Verwandte Suche: