Tiagabine
Catalog Number: BT-253173
CAS Number: 115103-54-3
Molecular Formula: C20H25NO2S2
Molecular Weight: 375.6 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Tiagabine is a medication used to treat epilepsy and is marketed under the brand name Gabitril. It is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor that increases the concentration of GABA in the brain, which helps to reduce seizures. Tiagabine was first approved by the US Food and Drug Administration (FDA) in 1997 and has since been used as a treatment for epilepsy.
Properties
CAS Number
115103-54-3
Product Name
Tiagabine
IUPAC Name
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
Molecular Formula
C20H25NO2S2
Molecular Weight
375.6 g/mol
InChI
InChI=1S/C20H25NO2S2/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)/t16-/m1/s1
InChI Key
PBJUNZJWGZTSKL-MRXNPFEDSA-N
SMILES
CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C
Solubility
In water, 6.6X10-1 mg/L at 25 °C (est)
2.11e-02 g/L
2.11e-02 g/L
Synonyms
(R)-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochloride
Gabitril
N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic acid
NO 328
NO 329
NO-328
NO-329
tiagabine
Tiagabine Hydrochloride
tiagabine, (S)-isome
Gabitril
N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic acid
NO 328
NO 329
NO-328
NO-329
tiagabine
Tiagabine Hydrochloride
tiagabine, (S)-isome
Canonical SMILES
CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C
Isomeric SMILES
CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)C
Method of Synthesis or Extraction
Tiagabine is synthesized through a multi-step process that involves the reaction of 2,5-dichlorophenylacetic acid with ethyl oxalyl chloride to form the corresponding acid chloride. This is then reacted with 1,2,4-triazole to form the intermediate compound, which is then reacted with 1,2,4,5-tetrahydro-3H-pyridazin-3-one to form tiagabine. The yield of this process is approximately 50%, and the process is considered to be efficient. However, the process involves the use of hazardous chemicals, and safety precautions must be taken to prevent accidents.
Chemical Structure and Biological Activity
The chemical structure of tiagabine consists of a 2,5-dichlorophenyl group, an ethyl group, a triazole group, and a pyridazinone group. Tiagabine acts as a selective Tiagabine reuptake inhibitor, which means that it blocks the reuptake of Tiagabine into presynaptic neurons, leading to an increase in the concentration of Tiagabine in the synaptic cleft. This increase in Tiagabine concentration helps to reduce seizures.
Biological Effects
Tiagabine has been shown to have a number of biological effects on cell function and signal transduction. It has been shown to increase the concentration of Tiagabine in the brain, which helps to reduce seizures. Tiagabine has also been shown to have potential therapeutic and toxic effects. It has been used to treat epilepsy, but it can also cause side effects such as dizziness, drowsiness, and nausea.
Applications
Tiagabine has a number of applications in medical research, including its role in drug development, clinical trials, and findings. It has been used to treat epilepsy, and clinical trials have shown that it is effective in reducing seizures. However, it can also cause side effects, and its use must be carefully monitored. In environmental research, tiagabine has been shown to have effects on ecosystems and can be used in pollution management. In industrial research, tiagabine can be used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account when using tiagabine in industrial settings.
Future Perspectives and Challenges
There are currently some limitations in the use and study of tiagabine, including its potential side effects and the need for careful monitoring of its use. However, there are also possible solutions and improvements that can be made to address these limitations. For example, new formulations of tiagabine may be developed that reduce the risk of side effects. In the future, tiagabine may also be used in new applications in scientific research, such as in the treatment of other neurological disorders. Overall, tiagabine has shown promise as a treatment for epilepsy, and further research is needed to fully understand its potential benefits and limitations.
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