Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25NO2S2 |
Molecular Weight | 375.5509 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1ccsc1C(=CCCN2CCC[C@]([H])(C2)C(=O)O)c3c(C)ccs3
InChI
InChIKey=PBJUNZJWGZTSKL-MRXNPFEDSA-N
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
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.drugs.com/pro/tiagabine.html | https://www.drugbank.ca/drugs/DB00906 | http://reference.medscape.com/drug/gabitril-tiagabine-343022 | https://www.ncbi.nlm.nih.gov/pubmed/8595791 | https://www.ncbi.nlm.nih.gov/pubmed/16420077 | https://www.ncbi.nlm.nih.gov/pubmed/15519917
Curator's Comment:: description was created based on several sources, including
https://www.drugs.com/pro/tiagabine.html | https://www.drugbank.ca/drugs/DB00906 | http://reference.medscape.com/drug/gabitril-tiagabine-343022 | https://www.ncbi.nlm.nih.gov/pubmed/8595791 | https://www.ncbi.nlm.nih.gov/pubmed/16420077 | https://www.ncbi.nlm.nih.gov/pubmed/15519917
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8057281 |
70.0 nM [IC50] | ||
Target ID: CHEMBL5208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8057281 |
917.0 µM [IC50] | ||
Target ID: CHEMBL3715 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8057281 |
1670.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | GABITRIL Approved UseGABITRIL (tiagabine hydrochloride) is indicated as adjunctive therapy in adults and children 12 years and older in the treatment of partial seizures. Launch Date8.7557761E11 |
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Primary | GABITRIL Approved UseGABITRIL (tiagabine hydrochloride) is indicated as adjunctive therapy in adults and children 12 years and older in the treatment of partial seizures. Launch Date8.7557761E11 |
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Primary | GABITRIL Approved UseGABITRIL (tiagabine hydrochloride) is indicated as adjunctive therapy in adults and children 12 years and older in the treatment of partial seizures. Launch Date8.7557761E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
552 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
265 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2190 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
826 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7555975 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAGABINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
320 mg single, oral Overdose Dose: 320 mg Route: oral Route: single Dose: 320 mg Co-administed with:: phenytoin, p.o(400 mg, single) Sources: Page: p.155 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Seizures Age Group: 30 Sex: M Population Size: 1 Sources: Page: p.155 |
Disc. AE: Drowsiness, Coma... AEs leading to discontinuation/dose reduction: Drowsiness Sources: Page: p.155Coma (grade 3) |
72 mg single, oral Overdose Dose: 72 mg Route: oral Route: single Dose: 72 mg Sources: Page: p.271 |
unhealthy, 46 n = 1 Health Status: unhealthy Condition: Depression Age Group: 46 Sex: F Population Size: 1 Sources: Page: p.271 |
Disc. AE: Stupor, Confusion... AEs leading to discontinuation/dose reduction: Stupor Sources: Page: p.271Confusion |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | Disc. AE | 320 mg single, oral Overdose Dose: 320 mg Route: oral Route: single Dose: 320 mg Co-administed with:: phenytoin, p.o(400 mg, single) Sources: Page: p.155 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Seizures Age Group: 30 Sex: M Population Size: 1 Sources: Page: p.155 |
Coma | grade 3 Disc. AE |
320 mg single, oral Overdose Dose: 320 mg Route: oral Route: single Dose: 320 mg Co-administed with:: phenytoin, p.o(400 mg, single) Sources: Page: p.155 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Seizures Age Group: 30 Sex: M Population Size: 1 Sources: Page: p.155 |
Confusion | Disc. AE | 72 mg single, oral Overdose Dose: 72 mg Route: oral Route: single Dose: 72 mg Sources: Page: p.271 |
unhealthy, 46 n = 1 Health Status: unhealthy Condition: Depression Age Group: 46 Sex: F Population Size: 1 Sources: Page: p.271 |
Stupor | Disc. AE | 72 mg single, oral Overdose Dose: 72 mg Route: oral Route: single Dose: 72 mg Sources: Page: p.271 |
unhealthy, 46 n = 1 Health Status: unhealthy Condition: Depression Age Group: 46 Sex: F Population Size: 1 Sources: Page: p.271 |
PubMed
Title | Date | PubMed |
---|---|---|
Psychiatric symptoms after therapy with new antiepileptic drugs: psychopathological and seizure related variables. | 2000 Jun |
|
Clinical evaluation of Gabitril and Lamictal for drug-resistant epilepsy in adults. | 2001 |
|
Concerns with antiepileptic drug initiation: safety, tolerability, and efficacy. | 2001 |
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Tiagabine in clinical practice. | 2001 |
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The management of refractory idiopathic epilepsies. | 2001 |
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Epileptic encephalopathy. | 2001 |
|
GABAergic mechanisms in epilepsy. | 2001 |
|
The new generation of GABA enhancers. Potential in the treatment of epilepsy. | 2001 |
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Behavioural effects of the new anticonvulsants. | 2001 |
|
Effects of antiepileptic drugs on cognition. | 2001 |
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Newer antiepileptic drugs: advantages and disadvantages. | 2001 Aug |
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Pharmacological characterization of the 6 Hz psychomotor seizure model of partial epilepsy. | 2001 Dec |
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Progress report on new antiepileptic drugs: a summary of the Fifth Eilat Conference (EILAT V). | 2001 Jan |
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Advances in the treatment of epilepsy. | 2001 Jul 1 |
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Improvement of stiff-person syndrome with tiagabine. | 2001 Jul 24 |
|
Pharmacologic management of epilepsy in the elderly. | 2001 May-Jun |
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Antiepileptic drugs for the acute and maintenance treatment of bipolar disorder. | 2001 Sep-Oct |
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The 'number needed to treat' with levetiracetam (LEV): comparison with the other new antiepileptic drugs (AEDs). | 2002 Apr |
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Tiagabine overdose can induce convulsive status epilepticus. | 2002 Jul |
|
Aggravation of partial seizures by antiepileptic drugs: is there evidence from clinical trials? | 2002 Jul 9 |
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Tiagabine in glial tumors. | 2002 Mar |
|
Contribution of GABAergic cortical circuitry in shaping somatosensory evoked scalp responses: specific changes after single-dose administration of tiagabine. | 2002 May |
|
Effects of tiagabine, a gamma-aminobutyric acid re-uptake inhibitor, on normal rat bladder function. | 2002 May |
|
Comparison of antiepileptic drugs tiagabine, lamotrigine, and gabapentin in mouse models of acute, prolonged, and chronic nociception. | 2002 Sep |
|
An open case series on the utility of tiagabine as an augmentation in refractory bipolar outpatients. | 2002 Sep |
|
[(3)H]Tiagabine binding to GABA transporter-1 (GAT-1) in suicidal depression. | 2002 Sep |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14511393
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.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
959
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NDF-RT |
N0000175753
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NDF-RT |
N0000008486
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WHO-VATC |
QN03AG06
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NCI_THESAURUS |
C264
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WHO-ATC |
N03AG06
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Code System | Code | Type | Description | ||
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C059205
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M10842
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PRIMARY | Merck Index | ||
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31914
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PRIMARY | RxNorm | ||
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6306
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TIAGABINE
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CHEMBL1027
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115103-54-3
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DB00906
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Z80I64HMNP
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C66602
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4818
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60648
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SUB11000MIG
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2648
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115103-54-3
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Tiagabine
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7527
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)