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HomeProduct name listTiagabine hydrochloride

Tiagabine hydrochloride

Synonym(s):(-)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride;(R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride monohydrate;(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid hydrochloride;Tiagabine hydrochloride monohydrate

  • CAS NO.:145821-59-6
  • Empirical Formula: C20H26ClNO2S2
  • Molecular Weight: 412.01
  • MDL number: MFCD07369025
  • EINECS: 200-659-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 15:53:33
Tiagabine hydrochloride Structural

What is Tiagabine hydrochloride?

Description

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

Chemical properties

White to Off-White Solid

Originator

Gabitril,Cephalon, Inc.,USA

The Uses of Tiagabine hydrochloride

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.

The Uses of Tiagabine hydrochloride

A GABA uptake inhibitor. Anticonvulsant.

The Uses of Tiagabine hydrochloride

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.

What are the applications of Application

Tiagabine Hydrochloride is an uptake inhibitor of GABA and also an anticonvulsant

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.

storage

Room temperature (desiccate)

References

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

Properties of Tiagabine hydrochloride

Melting point: >192oC dec.
alpha  D20 -11°
Flash point: 9℃
storage temp.  2-8°C
solubility  H2O: soluble10mg/mL, clear
form  powder
pka pKa1 3.3; pKa2 9.4(at 25℃)
color  white to beige
optical activity [α]/D -9 to -12°, c = 1 in H2O
Merck  14,9417
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol, or distilled water may be stored at -20° for up to 3 months.
CAS DataBase Reference 145821-59-6(CAS DataBase Reference)

Safety information for Tiagabine hydrochloride

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H370:Specific target organ toxicity, single exposure
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P311:Call a POISON CENTER or doctor/physician.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for Tiagabine hydrochloride

InChIKey YUKARLAABCGMCN-PKLMIRHRSA-N

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