CHEBI:85388 - tiagabine hydrochloride

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ChEBI Name tiagabine hydrochloride
ChEBI ID CHEBI:85388
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H26ClNO2S2
Net Charge 0
Average Mass 412.00900
Monoisotopic Mass 411.10935
InChI InChI=1S/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
InChIKey YUKARLAABCGMCN-PKLMIRHRSA-N
SMILES Cl.Cc1ccsc1C(=CCCN1CCC[C@H](C1)C(O)=O)c1sccc1C
Roles Classification
Biological Role(s): GABA reuptake inhibitor
A compound that inhibits the re-uptake of the neurotransmitter GABA from the synapse into the pre-synaptic neuron, so increasing the extracellular concentrations of the neurotransmitter and hence increasing neurotransmission.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
GABA reuptake inhibitor
A compound that inhibits the re-uptake of the neurotransmitter GABA from the synapse into the pre-synaptic neuron, so increasing the extracellular concentrations of the neurotransmitter and hence increasing neurotransmission.
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ChEBI Ontology
Outgoing tiagabine hydrochloride (CHEBI:85388) has part tiagabine(1+) (CHEBI:85387)
tiagabine hydrochloride (CHEBI:85388) has role anticonvulsant (CHEBI:35623)
tiagabine hydrochloride (CHEBI:85388) has role GABA reuptake inhibitor (CHEBI:85384)
tiagabine hydrochloride (CHEBI:85388) is a hydrochloride (CHEBI:36807)
IUPAC Name
(3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
Synonyms Sources
(−)-(R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid hydrochloride ChemIDplus
(−)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride ChEBI
(3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]-3-carboxypiperidinium chloride IUPAC
(3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid monohydrochloride ChEBI
Abbott 70569.HCl ChemIDplus
Abbott-70569.1 ChemIDplus
tiagabine HCl ChemIDplus
tiagabine monohydrochloride ChEBI
Brand Name Source
Gabitril ChemIDplus
Manual Xrefs Databases
D02097 KEGG DRUG
US2008064727 Patent
View more database links
Registry Numbers Types Sources
145821-59-6 CAS Registry Number ChemIDplus
6378452 Reaxys Registry Number Reaxys
Last Modified
02 April 2015