Molecular Identity
Tiagabine
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
PubChem CID: 60648
Tiagabine is a piperidinemonocarboxylic acid that is (R)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group.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. It has a role as an anticonvulsant and a GABA reuptake inhibitor. It is a piperidinemonocarboxylic acid, a member of thiophenes, a beta-amino acid and a tertiary amino compound. It is functionally related to a (R)-nipecotic acid. It is a conjugate base of a tiagabine(1+).
2D Structure
Properties
C20H25NO2S2
Molecular Formula
375.60
Molecular Weight
g/mol
375.1327
Exact Mass
Da
2.7
XLogP
Drug-like (Lipinski: < 5)
97
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
5
H-Bond Acceptors
474
Complexity
SMILES
Canonical SMILES
SMILES: CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)CIsomeric SMILES
SMILES: CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)CSynonyms(20)
tiagabine115103-54-3Tiagabina(R)-TiagabineTiagabinumAbbott-70569Z80I64HMNPABT-569 FREE BASE(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acidNO-050328 FREE BASEABBOTT-70569 FREE BASENNC-050328 FREE BASE(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acidNO-328ABBOTT-705691 FREE BASE
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Tiagabine
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