EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:9586 - tiagabine

ChEBI IDCHEBI:9586
ChEBI Nametiagabine
Stars
DefinitionA piperidinemonocarboxylic acid that is (R)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group. A GABA reuptake inhibitor, it is used (generally as the hydrochloride salt) for the treatment of epilepsy.
Last Modified22 February 2017
DownloadsMolfile
FormulaC20H25NO2S2
Net Charge0
Average Mass375.559
Monoisotopic Mass375.13267
SMILESCc1ccsc1C(=CCCN1CCC[C@@H](C(=O)O)C1)c1sccc1C
InChIInChI=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
InChIKeyPBJUNZJWGZTSKL-MRXNPFEDSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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.
Applications:
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.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
ChEBI Ontology
Outgoing Relation(s)
tiagabine (CHEBI:9586) has functional parent (R)-nipecotic acid (CHEBI:221278)
tiagabine (CHEBI:9586) has role anticonvulsant (CHEBI:35623)
tiagabine (CHEBI:9586) has role GABA reuptake inhibitor (CHEBI:85384)
tiagabine (CHEBI:9586) is a piperidinemonocarboxylic acid (CHEBI:26148)
tiagabine (CHEBI:9586) is a tertiary amino compound (CHEBI:50996)
tiagabine (CHEBI:9586) is a thiophenes (CHEBI:26961)
tiagabine (CHEBI:9586) is a β-amino acid (CHEBI:33706)
tiagabine (CHEBI:9586) is conjugate base of tiagabine(1+) (CHEBI:85387)
Incoming Relation(s)
tiagabine(1+) (CHEBI:85387) is conjugate acid of tiagabine (CHEBI:9586)
IUPAC Name 
(3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
INNs  Source
tiagabinaChemIDplus
tiagabineWHO MedNet
tiagabinumChemIDplus
tiagabineChemIDplus
Synonyms  Source
(R)-tiagabineChemIDplus
(R)-(−)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI
(−)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI
(−)-(R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acidChemIDplus
Manual XrefsDatabases
C07503KEGG COMPOUND
D08588KEGG DRUG
TiagabineWikipedia
DB00906DrugBank
HMDB0015042HMDB
WO8700171Patent
US5010090Patent
LSM-5700LINCS
2648DrugCentral
Registry NumbersSources
Reaxys:6375354Reaxys
CAS:115103-54-3KEGG COMPOUND
CAS:115103-54-3ChemIDplus
Citations