Tiagabine

Names

[ Name ]:
Tiagabine

[Synonym ]:
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride
(R)-(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic acid
acide (3R)-1-[4,4-bis(3-méthylthiophén-2-yl)but-3-én-1-yl]pipéridine-3-carboxylique chlorhydrate
NO-05-0328
Gabitril / NNC 05-328
Abbott-70569.1
(R)-N-[4,4-di-(3-methylthien-2-yl)but-3-enyl] nipecotic acid hydrochloride
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride (1:1)
(3R)-1-[4,4-Bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidin-3-carbonsäurehydrochlorid
TIGABINE
3-Piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-, (3R)-, hydrochloride (1:1)
(R)-1-[4,4-bis(3-methyl-thien-2-yl)-3-butenyl]-3-piperidinecarboxylic acid
(3R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid hydrochloride
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
TGB
Tiagabine
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride (1:1)
no328
4-bis(3-methyl-2-thienyl)-3-butenyl)-1-((r)-3-piperidinecarboxylicaci
(R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid hydrochloride (1:1)
Abbott-70569.HCl
MFCD00865317
3-piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-, (3R)-, hydrochloride

Biological Activity

[Description]:

Tiagabine(NO328) is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor.Target: GABA reuptake inhibitorTiagabine had an early onset of effect, as shown by significant reduction from baseline in mean HAM-A total score compared with placebo at week 1 (observed cases, p < .05). Tiagabine was generally well tolerated and not associated with changes in sexual functioning or depressive status. Symptoms of a discontinuation syndrome during taper were not observed. Tiagabine may be a useful treatment option for adult patients diagnosed with GAD [1]. Tiagabine was generally well tolerated; the most common adverse events were nausea, dizziness and headaches [2]. Tiagabine (0.1 microM), an antiepileptic drug that specifically inhibits the GAT-1 GABA transporter inhibited GABA uptake 50% in temporal cortex and 60-68% in white structures [3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[References]

[1]. Pollack, M.H., et al., The selective GABA reuptake inhibitor tiagabine for the treatment of generalized anxiety disorder: results of a placebo-controlled study. J Clin Psychiatry, 2005. 66(11): p. 1401-8.

[2]. Sheehan, D.V., et al., An open-label study of tiagabine in panic disorder. Psychopharmacol Bull, 2007. 40(3): p. 32-40.

[3]. Henjum, S. and B. Hassel, High-affinity GABA uptake and GABA-metabolizing enzymes in pig forebrain white matter: a quantitative study. Neurochem Int, 2007. 50(2): p. 365-70.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.208 g/cm3

[ Boiling Point ]:
568ºC at 760 mmHg

[ Melting Point ]:
192oC dec.

[ Molecular Formula ]:
C₂₀H₂₅NO₂S₂

[ Molecular Weight ]:
375.55

[ Flash Point ]:
297.3ºC

[ PSA ]:
97.02000

[ LogP ]:
5.78470

[ Vapour Pressure ]:
9.71E-14mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TM6128245

CHEMICAL NAME :: 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)-

CAS REGISTRY NUMBER :: 115103-54-3

LAST UPDATED :: 199801

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H25-N-O2-S2.Cl-H

MOLECULAR WEIGHT :: 412.04

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 mg/kg/21D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: EPIRE8 Epilepsy Research. (Elsevier Science Publishers B.V., POB 1527, 1000 BM, Amsterdam, Netherlands) V.1- 1987- Volume(issue)/page/year: 19,205,1994

Tiagabine

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds