CHEBI:9586 - tiagabine

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ChEBI Name tiagabine
ChEBI ID CHEBI:9586
Definition A piperidinemonocarboxylic acid that is (R)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group.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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H25NO2S2
Net Charge 0
Average Mass 375.54800
Monoisotopic Mass 375.133
InChI 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
InChIKey PBJUNZJWGZTSKL-MRXNPFEDSA-N
SMILES Cc1ccsc1C(=CCCN1CCC[C@H](C1)C(O)=O)c1sccc1C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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): 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.
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ChEBI Ontology
Outgoing 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 β-amino acid (CHEBI:33706)
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 conjugate base of tiagabine(1+) (CHEBI:85387)
Incoming 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 Sources
tiagabina ChemIDplus
tiagabine WHO MedNet
tiagabine ChemIDplus
tiagabinum ChemIDplus
Synonyms Sources
(−)-(R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid ChemIDplus
(−)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid ChEBI
(R)-(−)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid ChEBI
(R)-tiagabine ChemIDplus
Manual Xrefs Databases
2648 DrugCentral
C07503 KEGG COMPOUND
D08588 KEGG DRUG
DB00906 DrugBank
HMDB0015042 HMDB
LSM-5700 LINCS
Tiagabine Wikipedia
US5010090 Patent
WO8700171 Patent
View more database links
Registry Numbers Types Sources
115103-54-3 CAS Registry Number ChemIDplus
6375354 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10530690 PubMed citation Europe PMC
22592677 PubMed citation Europe PMC
23770680 PubMed citation Europe PMC
23997364 PubMed citation Europe PMC
24440890 PubMed citation Europe PMC
24500879 PubMed citation Europe PMC
25663257 PubMed citation Europe PMC
9097364 PubMed citation Europe PMC
9449883 PubMed citation Europe PMC
Last Modified
22 February 2017