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145821-59-6

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  • 3-Piperidinecarboxylicacid, 1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-, hydrochloride (1:1), (3R)- 145821-59-6

    Cas No: 145821-59-6

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  • 1 Kilogram

  • 10000 Metric Ton/Month

  • Shanghai Upbio Tech Co.,Ltd
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145821-59-6 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 145821-59-6 differently. You can refer to the following data:
1. Tiagabine hydrochloride is a whitish, odorless, crystalline powder with a molecular formula of C20H25NO2S2HCl and a molecular weight of 412.0. Tiagabine hydrochloride was originally synthesized by Novo Nordisk Pharmaceuticals in Denmark. It was licensed in Europe in 1996 and in the United States in 1997, under the brand name Gabitril1. Gabitril1 is available in the form of 2, 4, 12, and 16 mg tablets. It is marketed by Cephalon. The antiepileptic drug tiagabine is a lipophilic derivative of nipecotic acid. Nipecotic acid inhibits GABA reuptake, but does not cross the blood brain barrier and is effective against seizures in animal models only when injected in the cerebral ventricles (Croucher et al. 1983). Tiagabine’s lipophilic anchor permits the passage of nipecotic acid from the systemic circulation across the blood brain barrier to the central nervous system (Krogsgaard-Larsen et al. 2000).
2. White to Off-White Solid

Indications

Tiagabine is licensed by the United States Food and Drug Administration (FDA) for adjunctive therapy in adults, and children of 12 years and older in the treatment of partial seizures with or without secondary generalization. There is no evidence to support a broader spectrum of action in epilepsy (Ben-Menachem 1995; Bialer et al. 2007). Tiagabine is also licensed in Europe by the European Medicines Agency (EMEA) for the same indications.

Clinical Applications

Tiagabine is currently used as adjunctive treatment in adults and children 12 years and older, suffering from partial-onset seizures, which cannot be satisfactorily controlled with other antiepileptic drugs. This indication was based on the results of five multi-center, double-blind, placebo-controlled clinical trials (two cross over and three parallel group studies) that proved its efficacy in patients with refractory partial seizures. These studies included a total of 951 adult and adolescent patients treated with add-on tiagabine at doses ranging from 16 to 56 mg compared to placebo (Ben-Menachem 1995; Richens et al. 1995; Sachdeo et al. 1997; Kalviainen et al. 1998; Uthman et al. 1998; Crawford et al. 2001). An integrated analysis of these studies demonstrated a significant 50% reduction in all seizure types in 23% of the tiagabine-treated group compared to 9% of the placebotreated group during a 7–12 week period (Ben-Menachem 1995). Doses between 32 and 56 mg in three or four divided doses were more effective than placebo (Sachdeo et al. 1997; Uthman et al. 1998). There was a dose–response relationship with greater efficacy at 56 mg/day (Uthman et al. 1998).

Drug Interactions

Tiagabine has minimal potential interaction with other drugs (Leppik et al. 1999). Tiagabine is not known to cause either induction or inhibition of hepatic microsomal enzyme systems. Consequently tiagabine does not alter the plasma concentrations of other drugs including antiepileptic drugs that undergo hepatic metabolism (Gustavson et al. 1998a, b). However, enzyme-inducing drugs accelerate the hepatic metabolism of tiagabine (So et al. 1995). There is no clinically relevant interaction between tiagabine and digoxin (Snel et al. 1998).

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

Originator

Gabitril,Cephalon, Inc.,USA

Uses

Different sources of media describe the Uses of 145821-59-6 differently. You can refer to the following data:
1. 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.
2. 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.
3. A GABA uptake inhibitor. 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.

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.

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

Check Digit Verification of cas no

The CAS Registry Mumber 145821-59-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,8,2 and 1 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 145821-59:
(8*1)+(7*4)+(6*5)+(5*8)+(4*2)+(3*1)+(2*5)+(1*9)=136
136 % 10 = 6
So 145821-59-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H25NO2S2.ClH/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23;/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23);1H/t16-;/m1./s1

145821-59-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T3165)  Tiagabine Hydrochloride  >99.0%(HPLC)

  • 145821-59-6

  • 50mg

  • 410.00CNY

  • Detail
  • TCI America

  • (T3165)  Tiagabine Hydrochloride  >99.0%(HPLC)

  • 145821-59-6

  • 250mg

  • 1,390.00CNY

  • Detail
  • Sigma

  • (SML0035)  Tiagabine hydrochloride  ≥98% (HPLC)

  • 145821-59-6

  • SML0035-10MG

  • 657.54CNY

  • Detail
  • Sigma

  • (SML0035)  Tiagabine hydrochloride  ≥98% (HPLC)

  • 145821-59-6

  • SML0035-50MG

  • 2,669.94CNY

  • Detail

145821-59-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name tiagabine hydrochloride

1.2 Other means of identification

Product number -
Other names Tiagabine hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:145821-59-6 SDS

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