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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25NO2S2.ClH.H2O
Molecular Weight 430.024
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIAGABINE HYDROCHLORIDE MONOHYDRATE

SMILES

O.Cl.CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(O)=O)C3=C(C)C=CS3

InChI

InChIKey=KOZCGZMZXXVHCF-GGMCWBHBSA-N
InChI=1S/C20H25NO2S2.ClH.H2O/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;1H2/t16-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H25NO2S2
Molecular Weight 375.548
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tiagabine (trade name Gabitril) is an anticonvulsant medication used in the treatment of Partial Seizures. The precise mechanism by which Tiagabine exerts its antiseizure effect is unknown, although it is believed to be related to its ability to enhance the activity of gamma-aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Tiagabine binds to recognition sites associated with the GABA uptake carrier. It is thought that, by this action, Tiagabine blocks GABA uptake into presynaptic neurons, permitting more GABA to be available for receptor binding on the surfaces of post-synaptic cells. Tiagabine is approved by U.S. Food and Drug Administration (FDA) as an adjunctive treatment for partial seizures in individuals of age 12 and up. It may also be prescribed off-label by physicians to treat anxiety disorders and panic disorder as well as neuropathic pain (including fibromyalgia). For anxiety and neuropathic pain, tiagabine is used primarily to augment other treatments. Tiagabine may be used alongside selective serotonin reuptake inhibitors, serotonin-norepinephrine reuptake inhibitors, or benzodiazepines for anxiety, or antidepressants, gabapentin, other anticonvulsants, or opioids for neuropathic pain. The most common side effect of tiagabine is dizziness. Other side effects that have been observed with a rate of statistical significance relative to placebo include asthenia, somnolence, nervousness, memory impairment, tremor, headache, diarrhea, and depression.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
70.0 nM [IC50]
917.0 µM [IC50]
1670.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GABITRIL
Primary
GABITRIL

Cmax

ValueDoseCo-administeredAnalytePopulation
552 ng/mL
24 mg single, oral
TIAGABINE blood
Homo sapiens
265 ng/mL
10 mg 1 times / day multiple, oral
TIAGABINE blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2190 ng × h/mL
24 mg single, oral
TIAGABINE blood
Homo sapiens
826 ng × h/mL
10 mg 1 times / day multiple, oral
TIAGABINE blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
24 mg single, oral
TIAGABINE blood
Homo sapiens
6.5 h
10 mg 1 times / day multiple, oral
TIAGABINE blood
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
12-22 mg/day PO divided q8-12hr
Route of Administration: Oral
In Vitro Use Guide
The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) proliferation assay is based on conversion by mitochondrial dehydrogenases of the substrate containing a tetrazolium ring into blue formazan, detectable spectrophotometrically (10). The level of blue formazan is then used as indirect index of cell density. The astrocytes were set up in flat-bottomed 200-μl microplates, incubated at 37◦C in a humidified 5% CO2/95% air mixture, and treated with 1, 10, 50, and 100 μg/ml of Tiagabine for 48 h. Four hours before the end of the culture, 20 μl of 0.5% 3-(4,5-dimethylthiazol-2-yl)diphenyltetrazolium bromide in phosphate-buffered saline (PBS) was added to each microwell. After the incubation with the reagent, the supernatant was removed and replaced with 100 μl of acidified isopropanol and 20 μl of 3% (wt/vol) sodium dodecylsulfate (SDS) in water. The optical density of each sample was measured with a microplate spectrophotometer reader (Titertek Multiskan, Flow Laboratories) at 570 nm, and four replicates were performed for each sample.
Substance Class Chemical
Record UNII
OXB00SKC7R
Record Status Validated (UNII)
Record Version